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  Subjects -> CHEMISTRY (Total: 871 journals)
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CHEMISTRY (610 journals)                  1 2 3 4 | Last

Showing 1 - 200 of 735 Journals sorted alphabetically
2D Materials     Hybrid Journal   (Followers: 13)
Accreditation and Quality Assurance: Journal for Quality, Comparability and Reliability in Chemical Measurement     Hybrid Journal   (Followers: 26)
ACS Catalysis     Full-text available via subscription   (Followers: 42)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 20)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 20)
ACS Macro Letters     Full-text available via subscription   (Followers: 25)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 40)
ACS Nano     Full-text available via subscription   (Followers: 266)
ACS Photonics     Full-text available via subscription   (Followers: 13)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 23)
Acta Chemica Iasi     Open Access   (Followers: 2)
Acta Chimica Sinica     Full-text available via subscription   (Followers: 1)
Acta Chimica Slovaca     Open Access   (Followers: 1)
Acta Chimica Slovenica     Open Access  
Acta Chromatographica     Full-text available via subscription   (Followers: 8)
Acta Facultatis Medicae Naissensis     Open Access  
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 6)
Acta Scientifica Naturalis     Open Access   (Followers: 2)
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 5)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 8)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 5)
Advanced Functional Materials     Hybrid Journal   (Followers: 54)
Advanced Science Focus     Free   (Followers: 5)
Advances in Chemical Engineering and Science     Open Access   (Followers: 64)
Advances in Chemical Science     Open Access   (Followers: 15)
Advances in Chemistry     Open Access   (Followers: 20)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 19)
Advances in Drug Research     Full-text available via subscription   (Followers: 21)
Advances in Enzyme Research     Open Access   (Followers: 9)
Advances in Fluorine Science     Full-text available via subscription   (Followers: 7)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 15)
Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 9)
Advances in Materials Physics and Chemistry     Open Access   (Followers: 25)
Advances in Nanoparticles     Open Access   (Followers: 15)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 15)
Advances in Polymer Science     Hybrid Journal   (Followers: 43)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 17)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 18)
Advances in Quantum Chemistry     Full-text available via subscription   (Followers: 6)
Advances in Science and Technology     Full-text available via subscription   (Followers: 12)
African Journal of Bacteriology Research     Open Access  
African Journal of Chemical Education     Open Access   (Followers: 3)
African Journal of Pure and Applied Chemistry     Open Access   (Followers: 7)
Agrokémia és Talajtan     Full-text available via subscription   (Followers: 2)
Al-Kimia : Jurnal Penelitian Sains Kimia     Open Access  
Alkaloids: Chemical and Biological Perspectives     Full-text available via subscription   (Followers: 2)
AMB Express     Open Access   (Followers: 1)
Ambix     Hybrid Journal   (Followers: 3)
American Journal of Biochemistry and Biotechnology     Open Access   (Followers: 61)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 15)
American Journal of Chemistry     Open Access   (Followers: 29)
American Journal of Plant Physiology     Open Access   (Followers: 11)
American Mineralogist     Hybrid Journal   (Followers: 15)
Analyst     Full-text available via subscription   (Followers: 38)
Angewandte Chemie     Hybrid Journal   (Followers: 166)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 237)
Annales UMCS, Chemia     Open Access  
Annals of Clinical Chemistry and Laboratory Medicine     Open Access   (Followers: 5)
Annual Reports in Computational Chemistry     Full-text available via subscription   (Followers: 3)
Annual Reports Section A (Inorganic Chemistry)     Full-text available via subscription   (Followers: 4)
Annual Reports Section B (Organic Chemistry)     Full-text available via subscription   (Followers: 9)
Annual Review of Chemical and Biomolecular Engineering     Full-text available via subscription   (Followers: 12)
Annual Review of Food Science and Technology     Full-text available via subscription   (Followers: 13)
Anti-Infective Agents     Hybrid Journal   (Followers: 3)
Antiviral Chemistry and Chemotherapy     Hybrid Journal   (Followers: 1)
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 8)
Applied Spectroscopy     Full-text available via subscription   (Followers: 22)
Applied Surface Science     Hybrid Journal   (Followers: 31)
Arabian Journal of Chemistry     Open Access   (Followers: 5)
ARKIVOC     Open Access   (Followers: 1)
Asian Journal of Biochemistry     Open Access   (Followers: 1)
Atomization and Sprays     Full-text available via subscription   (Followers: 4)
Australian Journal of Chemistry     Hybrid Journal   (Followers: 7)
Autophagy     Hybrid Journal   (Followers: 2)
Avances en Quimica     Open Access  
Biochemical Pharmacology     Hybrid Journal   (Followers: 10)
Biochemistry     Full-text available via subscription   (Followers: 337)
Biochemistry Insights     Open Access   (Followers: 6)
Biochemistry Research International     Open Access   (Followers: 6)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 9)
Bioinspired Materials     Open Access   (Followers: 5)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 2)
Biointerphases     Open Access   (Followers: 1)
Biology, Medicine, & Natural Product Chemistry     Open Access   (Followers: 1)
Biomacromolecules     Full-text available via subscription   (Followers: 20)
Biomass Conversion and Biorefinery     Partially Free   (Followers: 10)
Biomedical Chromatography     Hybrid Journal   (Followers: 7)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 3)
BioNanoScience     Partially Free   (Followers: 5)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 122)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 84)
Bioorganic Chemistry     Hybrid Journal   (Followers: 10)
Biopolymers     Hybrid Journal   (Followers: 18)
Biosensors     Open Access   (Followers: 2)
Biotechnic and Histochemistry     Hybrid Journal   (Followers: 2)
Bitácora Digital     Open Access  
Boletin de la Sociedad Chilena de Quimica     Open Access  
Bulletin of the Chemical Society of Ethiopia     Open Access   (Followers: 2)
Bulletin of the Chemical Society of Japan     Full-text available via subscription   (Followers: 24)
Bulletin of the Korean Chemical Society     Hybrid Journal   (Followers: 1)
C - Journal of Carbon Research     Open Access   (Followers: 3)
Cakra Kimia (Indonesian E-Journal of Applied Chemistry)     Open Access  
Canadian Association of Radiologists Journal     Full-text available via subscription   (Followers: 2)
Canadian Journal of Chemistry     Hybrid Journal   (Followers: 10)
Canadian Mineralogist     Full-text available via subscription   (Followers: 6)
Carbohydrate Research     Hybrid Journal   (Followers: 26)
Carbon     Hybrid Journal   (Followers: 71)
Catalysis for Sustainable Energy     Open Access   (Followers: 7)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 7)
Catalysis Science and Technology     Free   (Followers: 8)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 3)
Catalysts     Open Access   (Followers: 9)
Cellulose     Hybrid Journal   (Followers: 7)
Cereal Chemistry     Full-text available via subscription   (Followers: 4)
ChemBioEng Reviews     Full-text available via subscription   (Followers: 1)
ChemCatChem     Hybrid Journal   (Followers: 8)
Chemical and Engineering News     Free   (Followers: 17)
Chemical Bulletin of Kazakh National University     Open Access  
Chemical Communications     Full-text available via subscription   (Followers: 73)
Chemical Engineering Research and Design     Hybrid Journal   (Followers: 26)
Chemical Research in Chinese Universities     Hybrid Journal   (Followers: 3)
Chemical Research in Toxicology     Full-text available via subscription   (Followers: 22)
Chemical Reviews     Full-text available via subscription   (Followers: 183)
Chemical Science     Open Access   (Followers: 23)
Chemical Technology     Open Access   (Followers: 21)
Chemical Vapor Deposition     Hybrid Journal   (Followers: 5)
Chemical Week     Full-text available via subscription   (Followers: 7)
Chemie in Unserer Zeit     Hybrid Journal   (Followers: 56)
Chemie-Ingenieur-Technik (Cit)     Hybrid Journal   (Followers: 24)
ChemInform     Hybrid Journal   (Followers: 8)
Chemistry & Biodiversity     Hybrid Journal   (Followers: 7)
Chemistry & Biology     Full-text available via subscription   (Followers: 32)
Chemistry & Industry     Hybrid Journal   (Followers: 6)
Chemistry - A European Journal     Hybrid Journal   (Followers: 153)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 16)
Chemistry and Materials Research     Open Access   (Followers: 20)
Chemistry Central Journal     Open Access   (Followers: 4)
Chemistry Education Research and Practice     Free   (Followers: 5)
Chemistry in Education     Open Access   (Followers: 9)
Chemistry International     Hybrid Journal   (Followers: 2)
Chemistry Letters     Full-text available via subscription   (Followers: 44)
Chemistry of Materials     Full-text available via subscription   (Followers: 247)
Chemistry of Natural Compounds     Hybrid Journal   (Followers: 9)
Chemistry World     Full-text available via subscription   (Followers: 19)
Chemistry-Didactics-Ecology-Metrology     Open Access   (Followers: 1)
ChemistryOpen     Open Access   (Followers: 1)
Chemkon - Chemie Konkret, Forum Fuer Unterricht Und Didaktik     Hybrid Journal  
Chemoecology     Hybrid Journal   (Followers: 4)
Chemometrics and Intelligent Laboratory Systems     Hybrid Journal   (Followers: 14)
Chemosensors     Open Access  
ChemPhysChem     Hybrid Journal   (Followers: 11)
ChemPlusChem     Hybrid Journal   (Followers: 2)
ChemTexts     Hybrid Journal  
CHIMIA International Journal for Chemistry     Full-text available via subscription   (Followers: 2)
Chinese Journal of Chemistry     Hybrid Journal   (Followers: 6)
Chinese Journal of Polymer Science     Hybrid Journal   (Followers: 11)
Chromatographia     Hybrid Journal   (Followers: 24)
Chromatography     Open Access   (Followers: 2)
Chromatography Research International     Open Access   (Followers: 6)
Clay Minerals     Full-text available via subscription   (Followers: 10)
Cogent Chemistry     Open Access  
Colloid and Interface Science Communications     Open Access  
Colloid and Polymer Science     Hybrid Journal   (Followers: 11)
Colloids and Interfaces     Open Access  
Colloids and Surfaces B: Biointerfaces     Hybrid Journal   (Followers: 6)
Combinatorial Chemistry & High Throughput Screening     Hybrid Journal   (Followers: 5)
Combustion Science and Technology     Hybrid Journal   (Followers: 22)
Comments on Inorganic Chemistry: A Journal of Critical Discussion of the Current Literature     Hybrid Journal   (Followers: 2)
Composite Interfaces     Hybrid Journal   (Followers: 7)
Comprehensive Chemical Kinetics     Full-text available via subscription   (Followers: 1)
Comptes Rendus Chimie     Full-text available via subscription  
Comptes Rendus Physique     Full-text available via subscription   (Followers: 1)
Computational and Theoretical Chemistry     Hybrid Journal   (Followers: 9)
Computational Biology and Chemistry     Hybrid Journal   (Followers: 11)
Computational Chemistry     Open Access   (Followers: 2)
Computers & Chemical Engineering     Hybrid Journal   (Followers: 10)
Coordination Chemistry Reviews     Full-text available via subscription   (Followers: 3)
Copernican Letters     Open Access   (Followers: 1)
Corrosion Series     Full-text available via subscription   (Followers: 6)
Critical Reviews in Biochemistry and Molecular Biology     Hybrid Journal   (Followers: 5)
Croatica Chemica Acta     Open Access  
Crystal Structure Theory and Applications     Open Access   (Followers: 4)
CrystEngComm     Full-text available via subscription   (Followers: 13)
Current Catalysis     Hybrid Journal   (Followers: 2)
Current Chromatography     Hybrid Journal  
Current Green Chemistry     Hybrid Journal  
Current Metabolomics     Hybrid Journal   (Followers: 5)
Current Microwave Chemistry     Hybrid Journal  
Current Opinion in Colloid & Interface Science     Hybrid Journal   (Followers: 9)
Current Opinion in Molecular Therapeutics     Full-text available via subscription   (Followers: 14)
Current Research in Chemistry     Open Access   (Followers: 8)
Current Science     Open Access   (Followers: 70)
Current Trends in Biotechnology and Chemical Research     Open Access   (Followers: 3)
Dalton Transactions     Full-text available via subscription   (Followers: 23)
Detection     Open Access   (Followers: 2)
Developments in Geochemistry     Full-text available via subscription   (Followers: 2)
Diamond and Related Materials     Hybrid Journal   (Followers: 12)
Dislocations in Solids     Full-text available via subscription  
Doklady Chemistry     Hybrid Journal  

        1 2 3 4 | Last

Journal Cover Carbohydrate Research
  [SJR: 0.612]   [H-I: 98]   [26 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
   Published by Elsevier Homepage  [3175 journals]
  • Structure of surface polysaccharides from Aeromonas sp. AMG272, a
           plant-growth promoting rhizobacterium isolated from rice rhizosphere
    • Authors: Rocío Contreras Sánchez-Matamoros; Antonio M. Gil-Serrano; M. Rosario Espuny; Francisco Javier Ollero; Manuel Megías; Miguel A. Rodríguez-Carvajal
      Pages: 1 - 6
      Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462
      Author(s): Rocío Contreras Sánchez-Matamoros, Antonio M. Gil-Serrano, M. Rosario Espuny, Francisco Javier Ollero, Manuel Megías, Miguel A. Rodríguez-Carvajal
      Aeromonas sp. AMG272 is a Gram-negative bacterium that has been isolated from agricultural soil and studied for its plant growth-promoting activities. Structures of the O-specific polysaccharide chain of the AMG272 lipopolysaccharide and its capsular polysaccharide were elucidated using GLC-MS and NMR spectroscopy. The structure of the O-specific polysaccharide, →4)-α-l-Rhap-(1 → 3)-β-d-GlcpNAc-(1→, has been found in other Aeromonas strains and related bacteria, whereas the structure of the capsular polysaccharide has not been reported before: →6)[β-d-Fucp3NAc4Ac-(1 → 3)]-α-d-GlcpNAc-(1 → 4)-α-d-Galp-(1 → 3)-α-d-GalpNAc-(1 → 4)-α-d-Galp-(1 → .
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.012
      Issue No: Vol. 462 (2018)
       
  • N-Glycosyltransferase from Aggregatibacter aphrophilus synthesizes
           glycopeptides with relaxed nucleotide-activated sugar donor selectivity
    • Authors: Yun Kong; Jiang Li; Xinyuan Hu; Yaoguang Wang; Qingyun Meng; Guofeng Gu; Peng George Wang; Min Chen
      Pages: 7 - 12
      Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462
      Author(s): Yun Kong, Jiang Li, Xinyuan Hu, Yaoguang Wang, Qingyun Meng, Guofeng Gu, Peng George Wang, Min Chen
      N-Glycosyltransferase (NGT) is an inverting glycosyltransferase for an unusual pathway of N-linked protein glycosylation and glycosylates polypeptides in the consensus sequon (N-(X≠P)-T/S) with hexose monosaccharides. Here, we expressed and characterized a novel N-glycosyltransferase from Aggregatibacter aphrophilus (named AaNGT). RP-HPLC and Mass Spectrometry were used to assay and quantify glycopeptide formation by AaNGT and determine its substrate specificities. AaNGT could utilize a variety of nucleotide-activated sugar donors, including UDP-Glc, UDP-Gal, UDP-Xyl, GDP-Glc, dGDP-Glc and UDP-GlcN, to glycosylate the tested peptides. To the best of our knowledge, AaNGT was the first identified natural glycosyltransferase able to transfer GlcN moiety onto asparagine residues. AaNGT also exhibited a different position-specific residue preference of substrate peptides from the NGT of Actinobacillus pleuropneumoniae (ApNGT). In vitro assays with diverse synthesized peptides revealed that AaNGT preferred different peptide substrates from ApNGT. The efficient glycosylation of natural short peptides by AaNGT showed its potential to modify important therapeutic mammalian N-glycoproteins.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.008
      Issue No: Vol. 462 (2018)
       
  • Comparative conformational studies of
           3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyhex-1-enitols at the DFT level
    • Authors: Andrzej Nowacki; Beata Liberek
      Pages: 13 - 27
      Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462
      Author(s): Andrzej Nowacki, Beata Liberek
      B3LYP and M06–2X optimization and MP2 single point calculations are reported for the 4 H 5 and 5 H 4 conformations of 3,4,6-tri-O-acetyl-D-allal, 3,4,6-tri-O-acetyl-D-galactal, 3,4,6-tri-O-acetyl-D-glucal, and 3,4,6-tri-O-acetyl-D-gulal. Significant discrepancies in predictions of relative energies and conformers' population for B3LYP and M06–2X optimized geometries are observed. Generally, B3LYP overestimates the conformers' energies with respect to MP2, whereas M06–2X slightly underestimates the conformers' energies. B3LYP failed to estimate the 4 H 5 ⇄ 5 H 4 conformational equilibrium for 3,4,6-tri-O-acetyl-D-galactal and 3,4,6-tri-O-acetyl-D-glucal. The M06–2X functional showed good agreement with experimental results for all glycals studied. The 4 H 5 ⇄ 5 H 4 conformational equilibrium for 3,4,6-tri-O-acetyl-D-allal and 3,4,6-tri-O-acetyl-D-gulal is governed by the vinylogous anomeric effect (VAE), whereas competition between the VAE and quasi 1,3-diaxial interactions influence this equilibrium for 3,4,6-tri-O-acetyl-D-galactal and 3,4,6-tri-O-acetyl-D-glucal. The orientation of the 4-OAc group influences the strength of the quasi 1,3-diaxial interactions between the 3-OAc and 5-CH2OAc groups. AIM analysis shows weak bonding interaction between the 3-OAc and 5-CH2OAc groups.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.013
      Issue No: Vol. 462 (2018)
       
  • Molecular interactions of the anticancer agent ellipticine with
           glycosaminoglycans by in silico analysis
    • Authors: Ferenc Zsila; Sergey A. Samsonov
      Pages: 28 - 33
      Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462
      Author(s): Ferenc Zsila, Sergey A. Samsonov
      The anticancer agent ellipticine (ELP) functions as a DNA intercalating drug. Depending on the pH of the medium, it exists both in a neutral and a protonated form. In acidic extracellular microenvironment characteristic to malignant tissues, charged ELP molecules can also bind to glycosaminoglycans (GAGs), linear anionic periodic polysaccharides, which interact with various protein targets affecting diverse cellular events. Although a previous experimental work indicated specific GAG binding of protonated ELP, the underlying molecular mechanisms remain to be elucidated. From a computational point of view, analysis of molecular systems containing GAGs is challenging due to their high flexibility, variability in sulfation patterns and a key role of electrostatics and solvent-mediated interactions. In the present study, molecular dynamics-based approaches were employed to model ELP-GAG interactions in order to unveil the atomistic details of this biologically relevant molecular system. We characterized dynamic and energetic properties of three kinds of ELP-GAG complexes to rationalize and complement the available experimental data. The results reported herein provide insight into possible molecular pathways by which biological actions of ELP are mediated.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.014
      Issue No: Vol. 462 (2018)
       
  • Structure and gene cluster of the O-antigen of Escherichia coli O54
    • Authors: Olesya I. Naumenko; Xi Guo; Sof'ya N. Senchenkova; Peng Geng; Andrei V. Perepelov; Alexander S. Shashkov; Bin Liu; Yuriy A. Knirel
      Pages: 34 - 38
      Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462
      Author(s): Olesya I. Naumenko, Xi Guo, Sof'ya N. Senchenkova, Peng Geng, Andrei V. Perepelov, Alexander S. Shashkov, Bin Liu, Yuriy A. Knirel
      Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O54 afforded an O-polysaccharide, which was studied by sugar analysis, solvolysis with anhydrous trifluoroacetic acid, and 1H and 13C NMR spectroscopy. Solvolysis cleaved predominantly the linkage of β-d-Ribf and, to a lesser extent, that of β-d-GlcpNAc, whereas the other linkages, including the linkage of α-l-Rhap, were stable under selected conditions (40 °C, 5 h). The following structure of the O-polysaccharide was established: →4)-α-d-GalpA-(1 → 2)-α-l-Rhap-(1 → 2)-β-d-Ribf-(1 → 4)-β-d-Galp-(1 → 3)-β-d-GlcpNAc-(1→ The O-antigen gene cluster of E. coli O54 was analyzed and found to be consistent in general with the O-polysaccharide structure established but there were two exceptions: i) in the cluster, there were genes for phosphoserine phosphatase and serine transferase, which have no apparent role in the O-polysaccharide synthesis, and ii) no ribofuranosyltransferase gene was present in the cluster. Both uncommon features are shared by some other enteric bacteria.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.04.001
      Issue No: Vol. 462 (2018)
       
  • Determination of the cell wall polysaccharide and teichoic acid structures
           from Lactococcus lactis IL1403
    • Authors: Evgeny Vinogradov; Irina Sadovskaya; Pascal Courtin; Saulius Kulakauskas; Thierry Grard; Jennifer Mahony; Douwe van Sinderen; Marie-Pierre Chapot-Chartier
      Pages: 39 - 44
      Abstract: Publication date: Available online 12 April 2018
      Source:Carbohydrate Research
      Author(s): Evgeny Vinogradov, Irina Sadovskaya, Pascal Courtin, Saulius Kulakauskas, Thierry Grard, Jennifer Mahony, Douwe van Sinderen, Marie-Pierre Chapot-Chartier
      In the lactic acid bacterium Lactococcus lactis, a cell wall polysaccharide (CWPS) is the bacterial receptor of the majority of infecting bacteriophages. The diversity of CWPS structures between strains explains, at least partially, the narrow host range of lactococcal phages. In the present work, we studied the polysaccharide components of the cell wall of the prototype L. lactis subsp. lactis strain IL1403. We identified a rhamnose-rich complex polysaccharide, carrying a glycerophosphate substitution, as the major component. Its structure was analyzed by 2D NMR spectroscopy, methylation analysis and MALDI-TOF MS and shown to be distinctly different from currently known lactococcal CWPS structures. It contains a linear backbone of repeated α-l-Rha disaccharide subunits, which is irregularly substituted with a trisaccharide occasionally bearing a glycerophosphate group. A poly (glycerol phosphate) teichoic acid, another important carbohydrate component of the IL1403 cell wall, was also isolated and structurally characterized.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.04.002
      Issue No: Vol. 462 (2018)
       
  • Metal-free oxidative esterification of benzylated monosaccharides
    • Authors: Tchambaga Camara; Abed Bil; Vincent Chagnault
      Pages: 45 - 49
      Abstract: Publication date: Available online 12 April 2018
      Source:Carbohydrate Research
      Author(s): Tchambaga Camara, Abed Bil, Vincent Chagnault
      Methyl glyconates have been attracting considerable attention as intermediates for the preparation of aryl C-glycosides, polyphenolic products, aliphatic polyesters, SGLT2 inhibitors, antibiotics etc … In view of the interest in those compounds, we report herein our work on the synthesis of methyl glyconates using an oxidative esterification carried out by molecular iodine. This reaction is catalyzed by non-toxic K4Fe(CN)6 that releases a small amount of cyanide ion into the reaction mixture. Four benzylated carbohydrates which contain a hemiacetalic functional group have been tested successfully.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.04.003
      Issue No: Vol. 462 (2018)
       
  • Pd(II)/PhI(OAc)2 promoted direct cross coupling of glucals with aromatic
           acids
    • Authors: Zubeda Begum; G. Shankar; K. Sirisha; B.V. Subba Reddy
      Pages: 1 - 3
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Zubeda Begum, G. Shankar, K. Sirisha, B.V. Subba Reddy
      A highly efficient oxidative C2-aroyloxylation of D-glucal with aromatic carboxylic acids has been achieved for the first time using 5 mol% Pd(OAc)2 and 1 equiv of PhI(OAc)2 to produce C2-aroyloxyglycals in good yields. The use of excess of PhI(OAc)2 (2 equiv) provides C2-acyloxyglycal exclusively.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.002
      Issue No: Vol. 461 (2018)
       
  • Peruvioses A to F, sucrose esters from the exudate of Physalis peruviana
           fruit as α-amylase inhibitors
    • Authors: Carlos-A. Bernal; Leonardo Castellanos; Diana M. Aragón; Diana Martínez-Matamoros; Carlos Jiménez; Yolima Baena; Freddy A. Ramos
      Pages: 4 - 10
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Carlos-A. Bernal, Leonardo Castellanos, Diana M. Aragón, Diana Martínez-Matamoros, Carlos Jiménez, Yolima Baena, Freddy A. Ramos
      The fruit of Physalis peruviana is widely used in traditional Colombian medicine as an antidiabetic treatment. The aim of the study reported here was to identify the compounds responsible for the hypoglycemic activity using the α-amylase inhibition test. Bioguided fractionation of a dichloromethane extract of the sticky exudate that covers the fruit allowed the isolation and identification of three new sucrose esters, named as peruvioses C–E (1–3), along with the known peruvioses A (6), B (5) and F (4), the structures of which were elucidated by extensive NMR and MS experiments. These compounds proved to be responsible for the hypoglycemic activity observed in the extract. Peruviose D (2) showed the highest activity, with an inhibitory activity value of 84.8%. This is the first study to establish the potential of sucrose esters as α-amylase inhibitors and to explain the hypoglycemic effect that has traditionally been attributed to gooseberry fruit.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.003
      Issue No: Vol. 461 (2018)
       
  • Charge effects of self-assembled chitosan-hyaluronic acid nanoparticles on
           inhibiting amyloid β-protein aggregation
    • Authors: Zhiqiang Jiang; Xiaoyan Dong; Yan Sun
      Pages: 11 - 18
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Zhiqiang Jiang, Xiaoyan Dong, Yan Sun
      Amyloid β-protein (Aβ) aggregation is crucial for the pathogenesis of Alzheimer's disease, and surface charge of nanoparticles (NPs) has been recognized as an important factor influencing Aβ aggregation. Herein, we report a systematic study on the issue with a series of self-assembled chitosan-hyaluronic acid composite (CH) NPs of different surface charges (CH1 to CH7, zeta potentials from +38 to −35 mV). Both the positive and negative CH NPs inhibited Aβ aggregation and the inhibitory effect increased with increasing the surface charges density. Circular dichroism spectroscopy and atomic force microscopy revealed the difference in their working mechanisms. Studies at different pH values further confirmed the importance of electrostatic interactions in Aβ aggregation and presented that the effects of CH NPs changed due to the change of Aβ charge property with pH. This work has thus provided new insight into the surface charge effects on Aβ aggregation.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.001
      Issue No: Vol. 461 (2018)
       
  • 5-Acetamido-3,5-dideoxy-L-glycero-L-manno-non-2-ulosonic acid-containing
           O-polysaccharide from marine bacterium Pseudomonas glareae KMM 9500T
    • Authors: Maxim S. Kokoulin; Anatoly I. Kalinovsky; Lyudmila A. Romanenko; Valery V. Mikhailov
      Pages: 19 - 24
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Maxim S. Kokoulin, Anatoly I. Kalinovsky, Lyudmila A. Romanenko, Valery V. Mikhailov
      The O-polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Pseudomonas glareae KMM 9500T and studied by chemical methods along with 1D and 2D 1H and 13C NMR spectroscopy including 1H,1H-TOCSY, 1H,1H-COSY, 1H,1H-ROESY, 1H,13C-HSQC and 1H,13C-HMBC experiments. The O-polysaccharide was found to consist of linear tetrasaccharide repeating units constituted by D-glucuronic acid (D-GlcA), L-rhamnose (L-Rha), D-glucose (D-Glc) and 5-acetamido-7,9-O-[(S)-1-carboxyethylidene]-3,5-dideoxy-L-glycero-L-manno-non-2-ulosonic acid (Sug7,9(S-Pyr)), partially O-acetylated at position 8 (∼70%): →4)-α-D-GlcpA-(1→3)-β-L-Rhap-(1→4)-β-D-Glcp-(1→4)-β-Sugp8Ac(∼70%)7,9(S-Pyr)-(2→
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.004
      Issue No: Vol. 461 (2018)
       
  • Structural studies of the cell wall polysaccharide from Lactococcus lactis
           UC509.9
    • Authors: Evgeny Vinogradov; Irina Sadovskaya; Thierry Grard; James Murphy; Jennifer Mahony; Marie-Pierre Chapot-Chartier; Douwe van Sinderen
      Pages: 25 - 31
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Evgeny Vinogradov, Irina Sadovskaya, Thierry Grard, James Murphy, Jennifer Mahony, Marie-Pierre Chapot-Chartier, Douwe van Sinderen
      Lactococcus lactis is the most widely utilised starter bacterial species in dairy fermentations. The L. lactis cell envelope contains polysaccharides, which, among other known functions, serve as bacteriophage receptors. Our previous studies have highlighted the structural diversity of these so-called cell wall polysaccharides (CWPSs) among L. lactis strains that could account for the narrow host range of most lactococcal bacteriophages. In the present work, we studied the CWPS of L. lactis strain UC509.9, an Irish dairy starter strain that is host to the temperate and well-characterized P335-type phage Tuc2009. The UC509.9 CWPS structure was analyzed by methylation, deacetylation/deamination, Smith degradation and 2D NMR spectroscopy. The CWPS consists of a linear backbone composed of a tetrasaccharide repeat unit, partially substituted with a branched phosphorylated oligosaccharide having a common trisaccharide and three non-stoichiometric substitutions.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.011
      Issue No: Vol. 461 (2018)
       
  • Synthesis of bidesmosidic lupane saponins – comparison of batch and
           continuous-flow methodologies
    • Authors: Anna Korda; Zbigniew Pakulski; Piotr Cmoch; Katarzyna Gwardiak; Romuald Karczewski
      Pages: 32 - 37
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Anna Korda, Zbigniew Pakulski, Piotr Cmoch, Katarzyna Gwardiak, Romuald Karczewski
      Synthesis of lupane bidesmosides was optimized. The title compounds were obtained by glycosylation of 3-O- or 28-O-substituted betulin monodesmosides with Schmidt donors catalyzed by TMSOTf. Classical batch procedure and microreactor technique were used and compared in the above synthesis. Experimental results clearly showed that both methods are comparable, although any particular outcome strongly depends on the structure of the reagents. Undesired allobetulin derivatives formed by the Wagner-Meerwein rearrangement were usually isolated in minute amounts. In the case of batch reaction, shorter reaction time significantly decreased formation of side-products.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.006
      Issue No: Vol. 461 (2018)
       
  • Inositol to aromatics –benzene free synthesis of poly oxygenated
           aromatics
    • Authors: Bharat P. Gurale; Mysore S. Shashidhar; Richa S. Sardessai; Rajesh G. Gonnade
      Pages: 38 - 44
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Bharat P. Gurale, Mysore S. Shashidhar, Richa S. Sardessai, Rajesh G. Gonnade
      A method for the preparation of benzene derivatives from myo-inositol, an abundantly available phyto chemical is described. 1,3-Bridged acetals of inososes undergo step-wise elimination leading to the formation of polyoxygenated benzene derivatives. This aromatization reaction proceeds through the intermediacy of a β-alkoxyenone, which could be isolated. This sequence of reactions starting from myo-inositol, provides a novel route for the preparation of polyoxygenated benzene derivatives including polyoxygenated biphenyl. This scheme of synthesis demonstrates the potential of myo-inositol as a sustainable non-petrochemical resource for aromatic compounds.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.007
      Issue No: Vol. 461 (2018)
       
  • 1-C-phosphonomethyl- and
           1-C-difluorophosphonomethyl-1,4-imino-l-arabinitols as Galf transferase
           inhibitors: A comparison
    • Authors: Chloé Cocaud; Ruixiang B. Zheng; Todd L. Lowary; Thomas Poisson; Xavier Pannecoucke; Cyril Nicolas; Olivier R. Martin
      Pages: 45 - 50
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Chloé Cocaud, Ruixiang B. Zheng, Todd L. Lowary, Thomas Poisson, Xavier Pannecoucke, Cyril Nicolas, Olivier R. Martin
      The convenient preparation of iminopentitol derivatives, based on a 1,4-dideoxy-1,4-imino-l-arabinitol scaffold carrying β-phosphono(difluoromethyl) or β-phosphonomethyl appendages, as Galf-1P mimics, is reported. The compounds were tested for their ability to inhibit GlfT2, a vital galactofuranosyltransferase involved in the cell wall biosynthesis of mycobacteria. Interestingly, the Galf-1P mimics lacking a fluorine atom (7 and 8) were very poor inhibitors, showing less than 20% inhibition of GlfT2, whereas compounds 2 and 3, which contains a difluoromethylenephosphonate moiety were more potent inhibitors. Compound 3 that is fully deprotected was the most potent showing a significant IC50 value (0.9 mm), despite the absence of the diphosphate linkage present in the parent sugar nucleotide. This study paves the way to the synthesis of more complex β-phosphonomethyl-imino-l-arabinitol derivatives as simplified mimics of UDP-α-d-Galf.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.009
      Issue No: Vol. 461 (2018)
       
  • XRD and solid state 13C-NMR evaluation of the crystallinity enhancement of
           13C-labeled bacterial cellulose biosynthesized by Komagataeibacter xylinus
           under different stimuli: A comparative strategy of analyses
    • Authors: Juan C. Meza-Contreras; Ricardo Manriquez-Gonzalez; José A. Gutiérrez-Ortega; Yolanda Gonzalez-Garcia
      Pages: 51 - 59
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Juan C. Meza-Contreras, Ricardo Manriquez-Gonzalez, José A. Gutiérrez-Ortega, Yolanda Gonzalez-Garcia
      The production and crystallinity of 13C bacterial cellulose (BC) was examined in static culture of Komagataeibacter xylinus with different chemical and physical stimuli: the addition of NaCl or cloramphenicol as well as exposure to a magnetic field or to UV light. Crystalline BC biosynthesized under each stimulus was studied by XRD and solid state 13C NMR analyses. All treatments produced BC with enhanced crystallinity over 90% (XRD) and 80% (NMR) compared to the control (83 and 76%, respectively) or to Avicel (77 and 62%, respectively). The XRD data indicated that the crystallite size was 80–85 Å. Furthermore, changes on the allomorphs (Iα and Iβ) ratio tendency of BC samples addressed to the stimuli were estimated using the C4 signal from 13C NMR data. These results showed a decrease of the allomorph Iα (3%) when BC was biosynthesized with UV light and chloramphenicol compared to control (58.79%). In contrast, the BC obtained with NaCl increased up to 60.31% of the Iα allomorph ratio.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.005
      Issue No: Vol. 461 (2018)
       
  • Synthesis and self-assembling properties of 4,6−O-benzylidene acetal
           protected D-glucose and D-glucosamine β−1,2,3−triazole derivatives
    • Authors: Anji Chen; Ifeanyi S. Okafor; Consuelo Garcia; Guijun Wang
      Pages: 60 - 75
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Anji Chen, Ifeanyi S. Okafor, Consuelo Garcia, Guijun Wang
      Sugar based low molecular weight gelators (LMWGs) are useful small molecules that can form reversible supramolecular gels with many applications. Selective functionalization of common monosaccharides has resulted in several classes of effective LMWGs. Recently we found that certain peracetylated sugars containing anomeric triazole functional groups were effective gelators. In this study we synthesized two series of 4,6-O-benzylidene acetal protected β-1,2,3-triazolyl glycoside of D-glucose and N-acetyl D-glucosamine derivatives and evaluated their self-assembling properties in a few solvents. Several gelators were obtained and the gelation properties of these compounds rely on the structures of the 4-triazolyl substituents. Typically, alkyl derivatives resulted in effective gelation in organic solvents and aqueous mixtures of ethanol and dimethyl sulfoxide. But further acetylation of these compounds resulted in loss of gelation properties. The gels were characterized using optical microscopy, rheology, and FTIR spectroscopy. We also analyzed the molecular assemblies, using 1H NMR spectroscopy to probe the influences of the hydroxyl, amide, and triazole functional groups. Naproxen was used as a model drug and it formed co-gels with compound 25 in DMSO water mixtures. Using UV spectroscopy, we found that naproxen was slowly released from the gel to aqueous solution. The general structure and gelation trend obtained here can be useful in designing sugar based biomaterials. We expect that further structural optimization can lead to more effective gelators that are compatible with different drug molecules for encapsulation and sustained release.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.011
      Issue No: Vol. 461 (2018)
       
  • Structure of
           3,6-dideoxy-3-[(R)-2-hydroxypropanoylamino]-D-galactose-containing
           O-polysaccharide from marine bacterium Simiduia litorea KMM 9504T
    • Authors: Maxim S. Kokoulin; Lyudmila A. Romanenko; Valery V. Mikhailov
      Pages: 76 - 79
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Maxim S. Kokoulin, Lyudmila A. Romanenko, Valery V. Mikhailov
      The O-polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Simiduia litorea KMM 9504T and studied by chemical methods along with 1D and 2D 1H and 13C NMR spectroscopy including 1H,1H-TOCSY, 1H,1H-COSY, 1H,1H-ROESY, 1H,13C-HSQC and 1H,13C-HMBC experiments. The following new structure of the O-polysaccharide of S. litorea KMM 9504T containing D-galacturonamide, 2-acetamido-2,6-dideoxy-D-glucose and 3,6-dideoxy-3-[(R)-2-hydroxypropanoylamino]-D-galactose was established: Image 2
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.010
      Issue No: Vol. 461 (2018)
       
  • Studies on the O-polysaccharide of Escherichia albertii O2 characterized
           by non-stoichiometric O-acetylation and non-stoichiometric side-chain
           l-fucosylation
    • Authors: Olesya I. Naumenko; Han Zheng; Yanwen Xiong; Sof'ya N. Senchenkova; Hong Wang; Alexander S. Shashkov; Qun Li; Jianping Wang; Yuriy A. Knirel
      Pages: 80 - 84
      Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461
      Author(s): Olesya I. Naumenko, Han Zheng, Yanwen Xiong, Sof'ya N. Senchenkova, Hong Wang, Alexander S. Shashkov, Qun Li, Jianping Wang, Yuriy A. Knirel
      An O-polysaccharide was isolated from the lipopolysaccharide of Escherichia albertii O2 and studied by chemical methods and 1D and 2D 1H and 13C NMR spectroscopy. The following structure of the O-polysaccharide was established: Image 2 . The O-polysaccharide is characterized by masked regularity owing to a non-stoichiometric O-acetylation of an l-fucose residue in the main chain and a non-stoichiometric side-chain l-fucosylation of a β-GlcNAc residue. A regular linear polysaccharide was obtained by sequential Smith degradation and alkaline O-deacetylation of the O-polysaccharide. The content of the O-antigen gene cluster of E. albertii O2 was found to be essentially consistent with the O-polysaccharide structure established.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.013
      Issue No: Vol. 461 (2018)
       
  • β-L-Arabinofuranosylation Conducted by
           5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl Trichloroacetimidate
    • Authors: Hong-Zhan Li; Jie Ding; Chun-Ru Cheng; Yue Chen; Xing-Yong Liang
      Pages: 1 - 7
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Hong-Zhan Li, Jie Ding, Chun-Ru Cheng, Yue Chen, Xing-Yong Liang
      We describe a β-L-arabinofuranosylation method by employing the 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl trichloroacetimidate 10 as a donor. This approach allows a wide range of acceptor substrates, especially amino acid acceptors, to be used. Stereoselective synthesis of β-(1,4)-L-arabinofuranosyl-(2S, 4R)-4-hydroxy-L-proline (β-L-Araf-L-Hyp4) and its dimer is achieved readily by this method. Both the stereoselectivities and yields of the reactions are excellent. To demonstrate the utility of this methodology, the preparation of a trisaccharide in a one-pot manner was carried out.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.006
      Issue No: Vol. 460 (2018)
       
  • Preparation and structural characterization of regioselective
           4-O/6-O-desulfated chondroitin sulfate
    • Authors: Wenwei Han; Quancai Li; Youjing Lv; QingChi Wang; Xia Zhao
      Pages: 8 - 13
      Abstract: Publication date: Available online 2 February 2018
      Source:Carbohydrate Research
      Author(s): Wenwei Han, Quancai Li, Youjing Lv, QingChi Wang, Xia Zhao
      The sulfation pattern plays a crucial role in chondroitin sulfate (CS) biological activity, and preparation of CS with defined structure is essential for accurate pharmacological study. In this study, we focused on the preparation of regioselective 4-O/6-O-desulfated CS derived from porcine, employing a dimethyl sulfoxide-methanol (DMSO-MeOH) method and an N-methyl-N-(trimethylsilyl) -trifluoroacetamide (MTSTFA) method CS, respectively. Results showed that the sulfate at C4 position (4-O-S) of N-acetylgalactosamine (GalNAc) was selectively removed by the DMSO-MeOH method, and the sulfate at C6 position (6-O-S) of GalNAc was selectively removed by the MTSTFA method. Structures of desulfated CS were characterized by means of FT-IR, NMR and disaccharide composition analysis. The preparations of regioselective 4-O/6-O-desulfated CS are powerful for the study of structure-activity relationship of CS.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
      DOI: 10.1016/j.carres.2018.01.010
      Issue No: Vol. 460 (2018)
       
  • Mechanochemical depolymerization of inulin
    • Authors: Haoran Xing; Varoujan A. Yaylayan
      Pages: 14 - 18
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Haoran Xing, Varoujan A. Yaylayan
      Although chemical reactions driven by mechanical force is emerging as a promising tool in the field of physical sciences, its applications in the area of food sciences are not reported. In this paper, we propose ball milling as an efficient tool for the controlled generation of fructooligosaccharide (FOS) mixtures from inulin with a degree of polymerization (dp) ranging between 4 and 7. The addition of catalytic amounts of AlCl3 together with ball milling (30 min, at 30 Hz) generated mixtures rich in dehydrated disaccharides such as di-D-fructose dianhydrides. Based on anion exchange chromatography in conjunction with ESI/qTOF/MS/MS analysis, catalysis increased the overall content of mono-, di-, and tri-saccharides by around 30 fold compared to un-catalyzed milling. In addition, dialysis results of the untreated and treated samples have indicated that under catalysis the percent of depolymerization (dp < 12) reached 73.4% from the starting value of 27.6% in the untreated sample. Both processes resulted in mixtures of prebiotic value. The use of mechanical energy may be suitable for a fast, cost-efficient and green conversion of inulin to value-added food ingredients.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.009
      Issue No: Vol. 460 (2018)
       
  • Efficient glycosylation of natural Danshensu and its enantiomer by sugar
           and 2-deoxy sugar donors
    • Authors: Katarzyna Sidoryk; Piotr Cmoch; Marta Świtalska; Bartosz Trzaskowski; Joanna Wietrzyk; Marcin Cybulski
      Pages: 19 - 28
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Katarzyna Sidoryk, Piotr Cmoch, Marta Świtalska, Bartosz Trzaskowski, Joanna Wietrzyk, Marcin Cybulski
      An efficient methodology of the glycosylation process of a secondary plant metabolite (R-Danshensu) and its enantiomer by sugar and 2-deoxy sugar donors was developed. The overall synthesis of the new sugar derivatives involved two steps, starting from the previously synthesized protected R and S Danshensu (1 and 2). The deoxy sugar derivatives of R and S Danshensu were obtained from available tri-O-acetyl-2-deoxy-D-glucal and di-O-acetyl-2-deoxy-D-ramnal. The direct glycosylation of 1 and 2 using glycal activation by an acid catalyst in all cases led to the α-anomers of deoxy sugar derivatives with good yields. As a result, a novel group of sugar and deoxy sugar conjugates with optically pure polyphenolic acids was successfully synthesized and their cytotoxic profile against two cancer cell lines was tested. An advantageous ADME profile and antiproliferative data classified this new group of compounds as a promising scaffold for further modification of more potent and selective anticancer agents.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.005
      Issue No: Vol. 460 (2018)
       
  • Synthesis of novel sugar or azasugar modified anthra[1,2-d]
           imidazole-6,11-dione derivatives and biological evaluation
    • Authors: Qiwei Wang; Chen Ma; Xueyan Li; Xiaofen Wang; Ruixue Rong; Chao Wei; Pingzhu Zhang; Xiaoliu Li
      Pages: 29 - 33
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Qiwei Wang, Chen Ma, Xueyan Li, Xiaofen Wang, Ruixue Rong, Chao Wei, Pingzhu Zhang, Xiaoliu Li
      A series of novel, sugar or azasugar modified anthra[1,2-d] imidazole-6,11-dione derivatives, with different side chain were synthesized, using the synthetic route of imidazole cyclization reaction of 1,2-diaminoanthraquinone with various sugar (azasugar)-derived aldehydes, and imidazole cyclization reaction of 1,2-diaminoanthraquinone with chloroacetic acid and then followed by the nucleophilic substitution of N-alkylamino azasugar. Their biological activities against HIV-RT and cytotoxic activities against A549, Hela and MCF-7 cells were preliminary evaluated, most compounds showed similar HIV-RT inhibition to the control drug (AZT).
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.012
      Issue No: Vol. 460 (2018)
       
  • Configuration-dependent complex formation between Ca(II) and sugar
           carboxylate ligands in alkaline medium: Comparison of L-gulonate with
           D-gluconate and D-heptaguconate
    • Authors: Bence Kutus; Csilla Dudás; Gábor Peintler; István Pálinkó; Pál Sipos
      Pages: 34 - 40
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Bence Kutus, Csilla Dudás, Gábor Peintler, István Pálinkó, Pál Sipos
      The calcium sugar carboxylate interactions in hyperalkaline solutions are of relevance in radioactive waste repositories and in certain industrial processes. The complex formation between L-gulonate and Ca2+ ions was studied in strongly alkaline medium at 25 °C and 1 M ionic strength and was compared with previous results reported for D-gluconate and D-heptagluconate. The deprotonation of the ligand was confirmed by potentiometric and 13C NMR spectroscopic measurements. Pronounced pH effects were seen in the presence of Ca2+ indicating strong complex formation. By the evaluation of the experimental data, two highly stable trinuclear species, Ca3Gul2H–3 + and the Ca3Gul2H–4 0, are formed in alkaline aqueous solutions. Polarimetric as well as 1H NMR spectroscopic measurements attested that the increased complex stability was due to the formation of strong metal ion - alcoholate interactions. Moreover, the 1H NMR spectra of the three anions refer to the role of configuration in metal ion-binding. That is, the participation of the C3-OH or C4-OH group is governed by the relative position (i.e., threo or erythro) of the C2-OH and C3-OH groups.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.01.012
      Issue No: Vol. 460 (2018)
       
  • Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A
           and ovatoside D
    • Authors: Shiqiang Yan; Sumei Ren; Ning Ding; Yingxia Li
      Pages: 41 - 46
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Shiqiang Yan, Sumei Ren, Ning Ding, Yingxia Li
      Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.
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      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.015
      Issue No: Vol. 460 (2018)
       
  • Structure and genetics of a glycerol 2-phosphate-containing O-specific
           polysaccharide of Escherichia coli O33
    • Authors: Sof'ya N. Senchenkova; Wenqi Hou; Olesya I. Naumenko; Peng Geng; Alexander S. Shashkov; Andrei V. Perepelov; Bin Yang; Yuriy A. Knirel
      Pages: 47 - 50
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Sof'ya N. Senchenkova, Wenqi Hou, Olesya I. Naumenko, Peng Geng, Alexander S. Shashkov, Andrei V. Perepelov, Bin Yang, Yuriy A. Knirel
      An O-specific polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Escherichia coli O33 followed by gel-permeation chromatography on Sephadex G-50. The polysaccharide was found to contain glycerol 2-phosphate (Gro-2-P), and the following structure of its tetrasaccharide repeat was established by sugar analysis, dephosphorylation, and 1D and 2D 1H and 13C NMR spectroscopy: Image 2 The O33-antigen gene cluster was analyzed and found to be essentially consistent with the O-polysaccharide structure.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.008
      Issue No: Vol. 460 (2018)
       
  • Full structure and insight into the gene cluster of the O-specific
           polysaccharide of Yersinia intermedia H9-36/83 (O:17)
    • Authors: Olga V. Sizova; Alexander S. Shashkov; Anna N. Kondakova; Yuriy A. Knirel; Rima Z. Shaikhutdinova; Sergei A. Ivanov; Angelina A. Kislichkina; Lidia A. Kadnikova; Aleksandr G. Bogun; Svetlana V. Dentovskaya
      Pages: 51 - 56
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Olga V. Sizova, Alexander S. Shashkov, Anna N. Kondakova, Yuriy A. Knirel, Rima Z. Shaikhutdinova, Sergei A. Ivanov, Angelina A. Kislichkina, Lidia A. Kadnikova, Aleksandr G. Bogun, Svetlana V. Dentovskaya
      Lipopolysaccharide was isolated from bacteria Yersinia intermedia H9-36/83 (O:17) and degraded with mild acid to give an O-specific polysaccharide, which was isolated by GPC on Sephadex G-50 and studied by sugar analysis and 1D and 2D NMR spectroscopy. The polysaccharide was found to contain 3-deoxy-3-[(R)-3-hydroxybutanoylamino]-d-fucose (d-Fuc3NR3Hb) and the following structure of the heptasaccharide repeating unit was established: Image 2 The structure established is consistent with the gene content of the O-antigen gene cluster. The O-polysaccharide structure and gene cluster of Y. intermedia are related to those of Hafnia alvei 1211 and Escherichia coli O:103.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.014
      Issue No: Vol. 460 (2018)
       
  • Efficient synthesis of a 6-deoxy-talose containing tetrasccharide found in
           Franconibacter helveticus LMG23732T
    • Authors: Yiren Xu; Tianheng Xu; Jianjun Zhang
      Pages: 57 - 65
      Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460
      Author(s): Yiren Xu, Tianheng Xu, Jianjun Zhang
      Synthesis of the 6-deoxy-talose (6-dTal) containing tetrasaccharide, naturally found in Franconibacter helveticus LMG23732T, has been described. The synthetic method utilized an allyloxyethylidene group for protecting the 1-OH and 2-OH groups of rhamnopyranose and a redox reaction for synthesizing 6-deoxy talose, which eventually formed a disaccharide containing α-Glcp-(1→2)-6dTalp configured glycosidic bonds using a [2 + 2] synthetic strategy.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.01.002
      Issue No: Vol. 460 (2018)
       
  • Synthesis and conformational analysis of
           d-gluco-pyranosyl-(6,6′)-d-gluco-pyranuronate, a model compound for the
           inter-glycan 6,6′-ester linkage
    • Authors: Sven Hackbusch; Amelia Watson; Andreas H. Franz
      Pages: 1 - 12
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Sven Hackbusch, Amelia Watson, Andreas H. Franz
      The synthesis of a 6,6′-ester linked disaccharide analog model compound was achieved in five steps from d-glucose and featured a key oxidative esterification transformation. The synthesized d- gluco-pyranosyl-(6,6′)-d- gluco-pyranuronate was characterized in D2O using NMR spectroscopy. Using the experimental data together with molecular dynamics simulations (TIP3P, water), a model of the compound's conformational behavior was established. The effect of the 6,6′-ester linkage on the solution phase structure was compared to that of the previously reported 6,6′-ether linkage in a disaccharide analog. Based on the established models, the ester linkage was found to have a profound effect on the overall shape of the molecule.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.01.005
      Issue No: Vol. 458-459 (2018)
       
  • New insight in crosslinking degree determination for crosslinked starch
    • Authors: Tingting Kou; Qunyu Gao
      Pages: 13 - 18
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Tingting Kou, Qunyu Gao
      The crosslinked starch has been studied for many years, but it is difficult to characterize degree of substitution on crosslinking of the very high and low crosslinked starches. The available approaches (including viscosity, settling volume, and P content) all have their limitations, i.e., not applicable in a large scope, pollution problem, and can not reflect the internal structure change. Here in this paper starch-iodine (St-I) method was proposed as a new approach to characterize the crosslinking degree. In this investigation, three starches of A, B, and C crystalline pattern with different amount (from very low to very high, 0.01, 0.05, 0.1, 0.5, 1, 5, 10%) of crosslinking reagent added were studied. This method is based on the mechanism that crosslinking reaction take place between amylose/amylopectin, amylopectin/amylopectin, whereas the amylose dose not crosslink one another. After crosslinked to amylopectin, the result amylose-amylopectin complex can be considered as a new amylopectin. Results showed that the St-I method can characterize all the crosslinked starches of the three starches, at low reagent level (0.01–0.1%), the amylose was found to decrease rapidly, this can also replace the viscosity method, whereas at high reagent level (1–10%), although the significant differences can still be observed, the effect was not so obvious as it for the lower crosslinked starches, here we firstly applied dose efficiency to characterize this phenomenon, which was informative and helpful in determining this modification process.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.01.009
      Issue No: Vol. 458-459 (2018)
       
  • Ab-initio and experimental study of pentose sugar dehydration mechanism in
           the gas phase
    • Authors: L. Antonini; S. Garzoli; A. Ricci; A. Troiani; C. Salvitti; P. Giacomello; R. Ragno; A. Patsilinakos; B. Di Rienzo; F. Pepi
      Pages: 19 - 28
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): L. Antonini, S. Garzoli, A. Ricci, A. Troiani, C. Salvitti, P. Giacomello, R. Ragno, A. Patsilinakos, B. Di Rienzo, F. Pepi
      In this work pentose sugar (D-xylose, D-ribose and D-arabinose) gas phase dehydration reaction was investigated by means of mass spectrometric techniques and theoretical calculations. The ionic species derived from the dehydration reaction of protonated D-ribose and D-arabinose were structurally characterized by their fragmentation patterns and the relative dehydration energies measured by energy resolved CAD mass spectra. The results were compared with those recently obtained for D-xylose in the same mass spectrometric experimental conditions. Dehydration of C1-OH protonated sugars was theoretically investigated at the CCSD(T)/cc-pVTZ//M11/6-311++G(2d,2p) level of theory. Protonated pentoses are not stable and promptly lose a water molecule giving rise to the dehydrated ions at m/z 133. D-xylose, D-ribose and D-arabinose dehydration follows a common reaction pathway with ionic intermediates and transition states characterized by similar structures. Slightly different dehydration energies were experimentally measured and the relative trend was theoretically confirmed. The overall dehydration activation energy follows the order arabinose < ribose < xylose. Gas-phase pentose sugar dehydration leads to the formation of protonated 2-furaldehyde as final product. Based on the experimental and theoretical evidence a new mechanistic hypothesis starting from C1-OH protonation was proposed.
      Graphical abstract image

      PubDate: 2018-02-13T18:23:18Z
      DOI: 10.1016/j.carres.2018.01.007
      Issue No: Vol. 458-459 (2018)
       
  • Partially methylated galactans containing different proportions of
           3-O-methyl-galactose from Pleurotus citrinopileatus
    • Authors: Dayane R. Brito; Elaine R. Carbonero; Sthefany R.F. Viana; Estefânia V. Silva; Andrea Caroline Ruthes; Luciano M. Lião; Marcello Iacomini
      Pages: 29 - 34
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Dayane R. Brito, Elaine R. Carbonero, Sthefany R.F. Viana, Estefânia V. Silva, Andrea Caroline Ruthes, Luciano M. Lião, Marcello Iacomini
      Pleurotus citrinopileatus, popularly known as “golden oyster mushroom” have medicinal properties, which are attributed mainly to the presence of bioactive polysaccharides. In this work, two partially 3-O-methylated galactans were isolated from the fruiting bodies of this fungus, via successive aqueous extraction, followed by fractionation by freeze-thawing, and precipitation of soluble material with Fehling solution. The structural assignments were carried out using mono- and bidimensional NMR spectroscopy, monosaccharide composition, and methylation analyses. The polysaccharides were characterized as linear, partially 3-O-methylated (1 → 6)-linked α-galactopyranans, containing only Gal and 3-O-Me-Gal, in 2:1 and 1:1 molar ratios, with molar masses of 37.6 × 103 g/mol and 28.5 × 103 g/mol, respectively. Similar structures have been described for other Pleurotus spp., but showing a lower content of 3-O-Me-Gal.
      Graphical abstract image

      PubDate: 2018-02-13T18:23:18Z
      DOI: 10.1016/j.carres.2018.02.002
      Issue No: Vol. 458-459 (2018)
       
  • Stereocontrolled synthesis of oleanolic saponin ladyginoside A isolated
           from Ladyginia bucharica
    • Authors: Matylda Stefaniak; Grzegorz Łopatkiewicz; Magdalena Antkowiak; Jacek Mlynarski
      Pages: 35 - 43
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Matylda Stefaniak, Grzegorz Łopatkiewicz, Magdalena Antkowiak, Jacek Mlynarski
      Efficient stereocontrolled synthesis of ladyginoside A isolated from Ladyginia bucharica is described. The presented methodology bases on the β-selective glycosylation to construct oleanate-3-O-β-glycoside from selectively protected d-cellobiose comprising desired β-linkage in carbohydrate unit. By using this procedure, dimethyl ester of ladyginoside A (1) (methyl oleanate 3-O-(β-d-glucopyranosyl)-(1 → 4)-β-d-glucuronide methyl ester) was obtained in 16% overall yield. Elaborated synthesis is also demonstrated as useful methodology en route to saponin 2 with additional glucose unit, namely 3-O-[β-d-glucopyranosyl-(1 → 4)-β-d-glucuronide] oleanolic acid 28-O-β-d-glucopyranosyl ester.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.01.011
      Issue No: Vol. 458-459 (2018)
       
  • Simultaneous formation of 3-deoxy-d-threo-hexo-2-ulose and
           3-deoxy-d-erythro-hexo-2-ulose during the degradation of d-glucose derived
           Amadori rearrangement products: Mechanistic considerations
    • Authors: Martin Kaufmann; Sophie Krüger; Clemens Mügge; Lothar W. Kroh
      Pages: 44 - 51
      Abstract: Publication date: Available online 12 February 2018
      Source:Carbohydrate Research
      Author(s): Martin Kaufmann, Sophie Krüger, Clemens Mügge, Lothar W. Kroh
      Analyzing classical model reaction systems of Amadori rearrangement products (ARP) it became apparent that the formation of 3-deoxy-d-threo-hexo-2-ulose (3-deoxygalactosone, 3-DGal) during the degradation of ARPs is highly dependent on pH and the amino acid residue of the respective ARP. Based on a detailed analysis of the NMR chemical shifts of the sugar moieties of different ARPs, it could be derived that the formation of 3-DGal is sensitive to the stability of a co-operative hydrogen bond network which involves HO-C3, the deprotonated carboxyl functionality and the protonated amino nitrogen of the amino acid substituent. Participating in this bond network, HO-C3 is partially protonated which facilitates the elimination of water at C3. Based on that, a new mechanism of 3-deoxyglycosone formation is proposed.
      Graphical abstract image

      PubDate: 2018-02-13T18:23:18Z
      DOI: 10.1016/j.carres.2018.01.006
      Issue No: Vol. 458-459 (2018)
       
  • NMR analysis of substrate binding to a two-domain chitinase: Comparison
           between soluble and insoluble chitins
    • Authors: Tomoya Takashima; Takayuki Ohnuma; Tamo Fukamizo
      Pages: 52 - 59
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Tomoya Takashima, Takayuki Ohnuma, Tamo Fukamizo
      CJP-4 is a two-domain chitinase from Japanese cedar (Cryptomeria japonica) pollen, consisting of an N-terminal CBM18 domain and a GH19 catalytic domain. The substrate binding to an inactive mutant protein of full-length CJP-4, in which the catalytic acid Glu108 was mutated to glutamine, CJP-4(E108Q), was analyzed by NMR spectroscopy. Based on the chemical shift perturbations of 1H-15N HSQC signals of Gly26 (CBM18 domain) and Trp185 (GH19 domain), the association constants for individual domains of CJP-4(E108Q) toward soluble chitin hexamer (GlcNAc)6 were determined to be 2300 and 3500 M−1, respectively. Isothermal titration calorimetry provided a similar association constant for (GlcNAc)6 (1980 M−1) with the one-site binding model. One (GlcNAc)6 molecule appeared to bind to a single binding site of CJP-4(E108Q), spanning from CBM18 to GH19 domains. When chitin nanofibers, insoluble chitinase substrate, were added to the CJP-4(E108Q) solution, strong line-broadening was observed for the majority of the backbone resonances in CBM18 domain but not in GH19 domain, indicating a binding preference of CBM18 domain to the insoluble chitin. We here demonstrated importance of CBM18 domain in insoluble chitin recognition based on the NMR binding data obtained for full-length CJP-4. Chitin nanofibers were found to be useful for spectroscopic observation of insoluble chitin binding to proteins.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.004
      Issue No: Vol. 458-459 (2018)
       
  • A new look at acid catalyzed deacetylation of carbohydrates: A
           regioselective synthesis and reactivity of 2-O-acetyl aryl
           glycopyranosides
    • Authors: Elena V. Stepanova; Marina O. Nagornaya; Victor D. Filimonov; Rashid R. Valiev; Maxim L. Belyanin; Anna K. Drozdova; Victor N. Cherepanov
      Pages: 60 - 66
      Abstract: Publication date: Available online 12 February 2018
      Source:Carbohydrate Research
      Author(s): Elena V. Stepanova, Marina O. Nagornaya, Victor D. Filimonov, Rashid R. Valiev, Maxim L. Belyanin, Anna K. Drozdova, Victor N. Cherepanov
      In the present work we report that acetyl groups of per – acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl3, which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. We have determined the influence of both carbohydrate moiety and the aglycon on the selectivity of deacetylation reaction by kinetic experiments. Using DFT/B3LYP/6-31G(d,p) and semi-empirical АМ1 methods we have found that the highest activation barrier is for 2-О-acetyl group. This completely explains the least reactivity of 2-О-acetyl group.
      Graphical abstract image

      PubDate: 2018-02-13T18:23:18Z
      DOI: 10.1016/j.carres.2018.02.003
      Issue No: Vol. 458-459 (2018)
       
  • Preparation and functional analysis of gossypols having two carbohydrate
           appendages with enaminooxy linkages
    • Authors: Yoshitsugu Amano; Masaki Nakamura; Shinya Shiraishi; Naoto Chigira; Nobuya Shiozawa; Masahito Hagio; Tomohiro Yano; Teruaki Hasegawa
      Pages: 67 - 76
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Yoshitsugu Amano, Masaki Nakamura, Shinya Shiraishi, Naoto Chigira, Nobuya Shiozawa, Masahito Hagio, Tomohiro Yano, Teruaki Hasegawa
      We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6.4–17 μM), due to their hydrophobic naphthyl rings. We also carried out WST-8 assays to assess the anticancer activity of the glycoGos on DLD-1 and HepG2 cells and found that the glycoGos having β-lactosides and having β-galactosides (specific ligands for asialoglycoprotein receptors) showed enhanced anticancer activity on HepG2 cells.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.001
      Issue No: Vol. 458-459 (2018)
       
  • Site-specific immobilization of endoglycosidases for streamlined
           chemoenzymatic glycan remodeling of antibodies
    • Authors: Tiezheng Li; Chao Li; David N. Quan; William E. Bentley; Lai-Xi Wang
      Pages: 77 - 84
      Abstract: Publication date: 22 March–15 April 2018
      Source:Carbohydrate Research, Volumes 458–459
      Author(s): Tiezheng Li, Chao Li, David N. Quan, William E. Bentley, Lai-Xi Wang
      Chemoenzymatic glycan remodeling of antibodies using an endoglycosidase and its mutant is emerging as an attractive approach for producing homogeneous antibody glycoforms. We report in this paper a site-specific covalent immobilization of the endoglycosidases (Endo-S2 and its glycosynthase mutant D184M) using a recombinant microbial transglutaminase (MTG) and evaluation of the immobilized enzymes in deglycosylation and glycosylation of a therapeutic antibody. The site-specific covalent immobilization was achieved by introduction of a Q-tag at the C-terminus of the recombinant enzymes followed by conjugation of the enzymes to a primary amine-containing solid support through MTG-catalyzed transglutamination. Using rituximab as a model system, we found that the Endo-S2 wild-type and D184M glycosynthase mutant immobilized by this approach were efficient in the two step antibody glycan remodeling to generate homogeneous antibody glycoforms. Notably using the covalently immobilized enzymes can efficiently avoid the need of intermediate purification and eliminate the residual contamination of wild type enzyme for product hydrolysis, thus streamlining the chemoenzymatic Fc glycan remodeling of antibodies.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.007
      Issue No: Vol. 458-459 (2018)
       
  • Scope and limitations of carbohydrate hydrolysis for de novo glycan
           sequencing using a hydrogen peroxide/metallopeptide-based glycosidase
           mimetic
    • Authors: Tianyuan Peng; Zachary Wooke; Nicola L.B. Pohl
      Pages: 85 - 88
      Abstract: Publication date: Available online 3 February 2018
      Source:Carbohydrate Research
      Author(s): Tianyuan Peng, Zachary Wooke, Nicola L.B. Pohl
      Acidic hydrolysis is commonly used as a first step to break down oligo- and polysaccharides into monosaccharide units for structural analysis. While easy to set up and amenable to mass spectrometry detection, acid hydrolysis is not without its drawbacks. For example, ring-destruction side reactions and degradation products, along with difficulties in optimizing conditions from analyte to analyte, greatly limits its broad utility. Herein we report studies on a hydrogen peroxide/CuGGH metallopeptide-based glycosidase mimetic design for a more efficient and controllable carbohydrate hydrolysis. A library of methyl glycosides consisting of ten common monosaccharide substrates, along with oligosaccharide substrates, was screened with the artificial glycosidase for hydrolytic activity in a high-throughput format with a robotic liquid handling system. The artificial glycosidase was found to be active towards most screened linkages, including alpha- and beta-anomers, thus serving as a potential alternative method for traditional acidic hydrolysis approaches of oligosaccharides.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
      DOI: 10.1016/j.carres.2018.01.008
      Issue No: Vol. 458-459 (2018)
       
  • Graphical abstract TOC
    • Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461


      PubDate: 2018-04-15T14:37:38Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 22 May 2018
      Source:Carbohydrate Research, Volume 461


      PubDate: 2018-04-15T14:37:38Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460


      PubDate: 2018-04-15T14:37:38Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 2 May 2018
      Source:Carbohydrate Research, Volume 460


      PubDate: 2018-04-15T14:37:38Z
       
  • A rapid synthesis of sphingosine from phytosphingosine
    • Authors: Arumugam Sankar; I-Cheng Chen; Shun-Yuan Luo
      Abstract: Publication date: Available online 13 April 2018
      Source:Carbohydrate Research
      Author(s): Arumugam Sankar, I-Cheng Chen, Shun-Yuan Luo
      A simple and efficient protocol for the synthesis of a sphingosine starting from cost-effective phytosphingosine has been described. Two alternative synthetic pathway have been disclosed based on the use of two different kinds of protective groups for the protection of the amino group in the phytosphingosine. The protected phytosphingosine was subsequently transformed into sphingosine in 5 steps i.e. protection of the amine group, protection of 1,3-diol, leaving group insertion, elimination, and one-pot deprotection.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.04.006
       
  • Synthesis of C-pyrimidyl nucleosides starting from alkynyl ribofuranosides
    • Authors: Grégory Legrave; Ramzi Ait Youcef; Damien Afonso; Angélique Ferry; Jacques Uziel; Nadège Lubin-Germain
      Abstract: Publication date: Available online 13 April 2018
      Source:Carbohydrate Research
      Author(s): Grégory Legrave, Ramzi Ait Youcef, Damien Afonso, Angélique Ferry, Jacques Uziel, Nadège Lubin-Germain
      The synthesis of four C-pyrimidyl nucleosides is described by condensation of small nitrogen molecules (amidines and ureas) onto alkynyl riboside derivatives. These last compounds were obtained by indium mediated stereoselective alkynylation of suitably protected ribose derivatives and the condensation reaction conditions were studied in order to favor the N-attack of the nitrogen molecules leading to the pyrimidine ring formation.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.04.005
       
  • Cytotoxic and glycosaminoglycan priming activities of novel
           4-anilinequinazoline β-D-xylosides
    • Authors: Jinpeng Wang; Yajing Chang; Xueyang Dong; Renshuai Zhang; Yang Tang; Meng Zhang; Rilei Yu; Tao Jiang; Lijuan Zhang
      Abstract: Publication date: Available online 13 April 2018
      Source:Carbohydrate Research
      Author(s): Jinpeng Wang, Yajing Chang, Xueyang Dong, Renshuai Zhang, Yang Tang, Meng Zhang, Rilei Yu, Tao Jiang, Lijuan Zhang
      β-D-xylosides with cytotoxic aglycones have augmented cytotoxicity towards animal cells because β-D-xyloside-primed glycosaminoglycans further enhance the aglycone's cytotoxicity. In this study, we designed and synthesized different 4-anilinequinazoline β-D-xylosides and found that compounds 7–10 possessing 3-chloro-4-((3-fluorobenzyl)oxy)aniline group as in anticancer drug lapatinib also primed glycosaminoglycans and were highly cytotoxic to cancer cells.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.04.007
       
 
 
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