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  Subjects -> CHEMISTRY (Total: 891 journals)
    - ANALYTICAL CHEMISTRY (55 journals)
    - CHEMISTRY (621 journals)
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    - INORGANIC CHEMISTRY (45 journals)
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CHEMISTRY (621 journals)                  1 2 3 4 | Last

Showing 1 - 200 of 735 Journals sorted alphabetically
2D Materials     Hybrid Journal   (Followers: 14)
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: 43)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 21)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 23)
ACS Macro Letters     Full-text available via subscription   (Followers: 26)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 41)
ACS Nano     Full-text available via subscription   (Followers: 272)
ACS Photonics     Full-text available via subscription   (Followers: 14)
ACS Symposium Series     Full-text available via subscription  
ACS Synthetic Biology     Full-text available via subscription   (Followers: 24)
Acta Chemica Iasi     Open Access   (Followers: 5)
Acta Chimica Slovaca     Open Access   (Followers: 2)
Acta Chimica Slovenica     Open Access   (Followers: 1)
Acta Chromatographica     Full-text available via subscription   (Followers: 9)
Acta Facultatis Medicae Naissensis     Open Access  
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 7)
Acta Scientifica Naturalis     Open Access   (Followers: 3)
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 6)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 9)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 6)
Advanced Functional Materials     Hybrid Journal   (Followers: 57)
Advanced Science Focus     Free   (Followers: 5)
Advances in Chemical Engineering and Science     Open Access   (Followers: 66)
Advances in Chemical Science     Open Access   (Followers: 18)
Advances in Chemistry     Open Access   (Followers: 21)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 19)
Advances in Drug Research     Full-text available via subscription   (Followers: 23)
Advances in Environmental Chemistry     Open Access   (Followers: 5)
Advances in Enzyme Research     Open Access   (Followers: 10)
Advances in Fluorine Science     Full-text available via subscription   (Followers: 9)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 17)
Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 11)
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: 16)
Advances in Polymer Science     Hybrid Journal   (Followers: 43)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 18)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 19)
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: 64)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 17)
American Journal of Chemistry     Open Access   (Followers: 30)
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: 165)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 244)
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: 2)
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 9)
Applied Spectroscopy     Full-text available via subscription   (Followers: 23)
Applied Surface Science     Hybrid Journal   (Followers: 31)
Arabian Journal of Chemistry     Open Access   (Followers: 6)
ARKIVOC     Open Access   (Followers: 1)
Asian Journal of Biochemistry     Open Access   (Followers: 2)
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: 349)
Biochemistry Insights     Open Access   (Followers: 6)
Biochemistry Research International     Open Access   (Followers: 6)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 10)
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: 2)
Biomacromolecules     Full-text available via subscription   (Followers: 21)
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: 128)
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: 8)
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: 10)
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: 18)
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: 190)
Chemical Science     Open Access   (Followers: 24)
Chemical Technology     Open Access   (Followers: 24)
Chemical Vapor Deposition     Hybrid Journal   (Followers: 5)
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: 7)
Chemistry - A European Journal     Hybrid Journal   (Followers: 162)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 16)
Chemistry and Materials Research     Open Access   (Followers: 21)
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: 253)
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   (Followers: 1)
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: 4)
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)
Communications Chemistry     Open Access  
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: 69)
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  

        1 2 3 4 | Last

Journal Cover
Carbohydrate Research
Journal Prestige (SJR): 0.617
Citation Impact (citeScore): 2
Number of Followers: 26  
 
  Hybrid Journal Hybrid journal (It can contain Open Access articles)
ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
Published by Elsevier Homepage  [3163 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.
      Graphical abstract image

      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.
      Graphical abstract image

      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.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.03.009
      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.
      Graphical abstract image

      PubDate: 2018-04-15T14:37:38Z
      DOI: 10.1016/j.carres.2018.02.011
      Issue No: Vol. 461 (2018)
       
  • Structures of O-specific polysaccharides of Pseudomonas psyhrotolerans BIM
           B-1158G
    • Abstract: Publication date: 30 July 2018
      Source:Carbohydrate Research, Volume 465
      Author(s): Evelina L. Zdorovenko, Alexander S. Shashkov, Alexandra A. Kadykova, Elena P. Kiseleva, Victoria V. Savich, Galina I. Novik, Yuriy A. Knirel
      Strain of Pseudomonas psychrotolerans was cultured on the nutrient agar and in a liquid nutrient broth. Bacterial cells were phage-typed with bacteriophages specific to Pseudomonas. O-antigen was isolated from cells using phenol-water method and mild acid degradation. The following structures of the polysaccharides extracted were established by sugar analysis and 1D, 2D NMR spectroscopy: PSI→3)-α-D-Manp-(1→2)-α-D-Manp-(1→; PSII→3)-α-D-Rhap-(1→2)-β-D-Rhap-(1→3)-α-D-Rhap-(1→; α-D-Glcp-(1˩; 2
      Graphical abstract image

      PubDate: 2018-06-18T10:13:01Z
       
  • Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and
           its related glycosides
    • Abstract: Publication date: Available online 8 June 2018
      Source:Carbohydrate Research
      Author(s): Takashi Matsumoto, Takuya Nakajima, Takehiro Iwadate, Ken-ichi Nihei
      Isotachioside (1) and its related natural product 2 are isolated from Isotachis japonica and Protea neriifolia, respectively, and are categorized as analogs of arbutin (3), a tyrosinase inhibitor for practical use. Both of the natural products and several derivatives such as glucoside 4, xyloside 5, cellobioside 6, and maltoside 7 were synthesized via Schmidt glycosylation as a key step, and their tyrosinase inhibitory activity was evaluated. The half maximal inhibitory concentration (IC50) of 1–3 could not be determined even when the concentration was increased to 1000 μM. Contrastingly, glycosides 4–7, missing methyl and benzoyl groups, acted as tyrosinase inhibitors with IC50s of 417 μM, 852 μM, 623 μM, and 657 μM, respectively. Among these novel inhibitors, derivative 4 was the most potent, indicating that the structural combination of resorcinol and glucose was significant for inducing the inhibitory effect.
      Graphical abstract image

      PubDate: 2018-06-11T10:08:09Z
       
  • Improved de novo sequencing of heparin/heparan sulfate oligosaccharides by
           propionylation of sites of sulfation
    • Abstract: Publication date: Available online 8 June 2018
      Source:Carbohydrate Research
      Author(s): Quntao Liang, Pradeep Chopra, Geert-Jan Boons, Joshua S. Sharp
      The structure of heparin and heparan sulfate (Hep/HS) oligosaccharides, as determined by the length and the pattern of sulfation, acetylation, and uronic acid epimerization, dictates their biological function through modulating interactions with protein targets. But fine structural determination is a very challenging task due to the lability of the sulfate modifications and difficulties in separating isomeric HS chains. Previously, we reported a strategy for chemical derivatization involving permethylation, desulfation, and trideuteroperacetylation, combined with standard reverse phase LC-MS/MS that enables the structural sequencing for heparin/HS oligosaccharides of sizes up to dodecasaccharide by positionally replacing all sulfates with more stable trideuteroacetyl groups, allowing for robust MS/MS sequencing. However, isomeric oligosaccharides that contain both N-sulfation and N-acetylation become isotopomers after labeling, differing only in the sites of deuteration. This prevents chromatographic separation of these different mixed domain sequences post-derivatization, and makes sequencing by MS/MS difficult due to co-fragmentation of the isotopomers leading to chimeric product ion spectra. In order to improve chromatographic separation of mixed domain oligosaccharides, we have introduced a propionylation step in place of trideuteroacetylation for labeling of sites of sulfation. HS standard disaccharides have been used to evaluate the efficiency of this improved chemical derivatization. The results show that we can quantitatively replace sulfation with propionyl groups with the same high efficiency as the previously reported trideuteroacetylation. After derivatization, we demonstrate the ability to chromatographically separate two mixed domain tetrasaccharide isomers differing solely by the order of N-sulfation and N-acetylation, allowing for full sequencing of each by MS/MS. These results represent a marked improvement in the ability of our previously reported derivatization strategy to analyze complex mixtures of Hep/HS oligosaccharides without a decrease in sensitivity.
      Graphical abstract image

      PubDate: 2018-06-11T10:08:09Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464


      PubDate: 2018-06-08T10:06:38Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464


      PubDate: 2018-06-08T10:06:38Z
       
  • Structure of the O-specific polysaccharide from Azospirillum fermentarium
           CC-LY743T
    • Abstract: Publication date: Available online 6 June 2018
      Source:Carbohydrate Research
      Author(s): Elena N. Sigida, Yuliya P. Fedonenko, Alexander S. Shashkov, Svetlana A. Konnova, Vladimir V. Ignatov
      O-specific polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide of nitrogen-fixing bacterium Azospirillum fermentarium CC-LY743T (IBPPM 578) and was studied by sugar analysis along with 1H and 13C NMR spectroscopy, including 1H,1H COSY, TOCSY, ROESY, and 1H,13C HSQC and HMBC experiments. The polysaccharide was found to be linear and to consist of alterating α-l-fucose and α-d-mannose residues in tetrasaccharide repeating units of the following structure: →2)-α-D-ManIp-(1 → 3)-α-L-FucIp-(1 → 3)-α-D-ManIIp-(1 → 3)-α-L-FunIIp-(1→
      Graphical abstract image

      PubDate: 2018-06-08T10:06:38Z
       
  • Stereoselective synthesis of 1,2-annulated-C-Aryl glycosides from
           carbohydrate-derived terminally unsubstituted dienes and arynes:
           Application towards synthesis of sugar-fused- or branched- naphthalenes,
           and C-Aryl glycosides
    • Abstract: Publication date: Available online 6 June 2018
      Source:Carbohydrate Research
      Author(s): Sateesh Dubbu, Ashish Kumar Verma, Kadigachalam Parasuraman, Yashwant D. Vankar
      Synthesis of 1,2-annulated-C-aryl glycosides has been achieved in a stereoselective manner through the Diels-Alder reaction between carbohydrate-derived terminally unsubstituted dienes and in situ generated arynes. In these reactions, formation of sugar-fused (or branched) naphthalenes was also observed and found to be temperature dependent and thus constituting one of the salient features of this work. The synthetic importance of 1,2-annulated-C-aryl glycosides has been explored by transforming them into densely oxygenated products by functionalizing the unsubstitued exo-double bond. Further, 1,2-annulated-C-aryl glycosides give rapid access to C-aryl glycosides in four steps.
      Graphical abstract image

      PubDate: 2018-06-08T10:06:38Z
       
  • Efficient synthesis of a linear octyl pentaarabinofuranoside, a substrate
           for mycobacterial EmbA/EmbB proteins
    • Abstract: Publication date: Available online 29 May 2018
      Source:Carbohydrate Research
      Author(s): Yue Chu, Jin-Song Yang
      The efficient synthesis of a linear pentasaccharide with the structure 1, β-D-Araf-(1 → 2)-α-D-Araf-(1 → 5)-α-D-Araf-(1 → 5)-α-D-Araf-(1 → 5)-α-D-Araf-(1 → 5), as its octyl glycoside has been achieved through a convergent [3 + 2] coupling strategy. The difficult-to-obtain 1,2-cis-β-arabinofuranosidic bond at the non-reducing end of the target molecule was stereoselectively constructed by the use of a 2-quinolinecarbonyl-directed 1,2-cis glycosylation method.
      Graphical abstract image

      PubDate: 2018-05-30T16:30:52Z
       
  • Synthesis and glycosidase inhibition potency of all-trans substituted
           1-C-perfluoroalkyl iminosugars
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464
      Author(s): Fabien Massicot, Richard Plantier-Royon, Jean-Luc Vasse, Jean-Bernard Behr
      Synthetic analogues of the naturally occurring iminosugar homoDMDP, which feature a perfluoroalkyl group at the pseudo-anomeric position, have been synthesized from the corresponding sugar-derived cyclic aldonitrone. The new fluorinated iminosugars as well as homoDMDP and its 6-deoxy counterpart were evaluated for their inhibitory activity against a panel of glycosidases. While the replacement of the (1′,2′)-dihydroxyethyl substituent of homoDMDP with –C4F9 proved detrimental for enzyme binding, introduction of a –C3F7 moiety tuned the inhibitory activity spectrum selectively towards α-fucosidase and α-glucosidase from yeast.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Application of a Janus aglycon with dual function in benzyl-free synthesis
           of spacer-armed oligosaccharide fragments of polysaccharides from
           rhizobacterium Azospirillum brasilense sp7
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464
      Author(s): Polina I. Abronina, Alexander I. Zinin, Denis A. Romashin, Valeria V. Tereshina, Alexander O. Chizhov, Leonid O. Kononov
      Both protective and pre-spacer features of 4-(2-chloroethoxy)phenyl (CEP) aglycon, which belong to the class of Janus aglycons, were engaged in a benzyl-free synthesis of oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7. Introduction of α-1,4-linked L-fucose residue was performed using 3,4-di-O-benzoyl-2-O-triisopropylsilyl-α-L-fucopyranosyl N-phenyltrifluoroacetimidate in excellent stereoselectivity and high yields. The obtained deprotected di-, tri- and tetrasaccharides contain 4-(2-azidoethoxy)phenyl (AEP) spacer aglycon, which allows straightforward preparation of neoglycoconjugates that will be used for the study of the role of lipopolysaccharide of rhizobacterium A. brasilense sp7 in plant–microbe symbiosis. The intermediate protected oligosaccharide building blocks with cleavable CEP/AEP aglycons have a strong potential for further application in the synthesis of more complex oligosaccharides.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • An anticoagulant fucan sulfate with hexasaccharide repeating units from
           the sea cucumber Holothuria albiventer
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464
      Author(s): Ying Cai, Wenjiao Yang, Ronghua Yin, Lutan Zhou, Zhongkun Li, Mingyi Wu, Jinhua Zhao
      A fucan sulfate was isolated and purified from the sea cucumber Holothuria albiventer by papain enzymolysis, alkaline hydrolysis and ion-exchange chromatography. The water-soluble polysaccharide had high molecular weight and contained fucose and sulfate in a molar ratio of about 1:0.83. Methylation analysis of the native polysaccharide indicated that its glycosidic linkages and sulfate substituents might be at O-3 or O-3, 4 or O-2, 3, or O-2, 3, 4 positions. FT-IR and 2D NMR spectroscopies further revealed that the fucan sulfate is characteristically composed of a regular α (1 → 3) linked hexasaccharide repeating unit which is substituted with sulfate esters in a distinctive pattern. Anticoagulant properties of the fucan sulfate and its depolymerized product were assessed in vitro in comparison with a low-molecular-weight heparin. The fucan sulfate exhibits strong APTT and TT prolonging activities and intrinsic factor Xase inhibitory activity, and its molecular size seemed to be required for these activities.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Large scale preparation of high mannose and paucimannose N-glycans from
           soybean proteins by oxidative release of natural glycans (ORNG)
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464
      Author(s): Yuyang Zhu, Maomao Yan, Yi Lasanajak, David F. Smith, Xuezheng Song
      Despite the important advances in chemical and chemoenzymatic synthesis of glycans, access to large quantities of complex natural glycans remains a major impediment to progress in Glycoscience. Here we report a large-scale preparation of N-glycans from a kilogram of commercial soy proteins using oxidative release of natural glycans (ORNG). The high mannose and paucimannose N-glycans were labeled with a fluorescent tag and purified by size exclusion and multidimensional preparative HPLC. Side products are identified and potential mechanisms for the oxidative release of natural N-glycans from glycoproteins are proposed. This study demonstrates the potential for using the ORNG approach as a complementary route to synthetic approaches for the preparation of multi-milligram quantities of biomedically relevant complex glycans.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Structural and genetic relatedness of the O-antigens of Escherichia coli
           O50 and O2
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464
      Author(s): Bin Yang, Sof'ya N. Senchenkova, Olesya I. Naumenko, Alexander S. Shashkov, Bin Liu, Andrey V. Perepelov, Yuriy A. Knirel
      An O-specific polysaccharide (O-antigen) was isolated by mild acid degradation of the lipopolysaccharide of Escherichia coli O50 followed by gel chromatography on Sephadex G-50. The following structure of the tetrasaccharide repeat was established by sugar analysis and 1D and 2D 1H and 13C NMR spectroscopy: →3)-α-l-Rhap-(1 → 2)-α-l-Rhap-(1 → 3)-β-l-Rhap-(1 → 4)-β-d-GlcpNAc-(1→ The linear O50 polysaccharide has the same structure as the main chain of the branched O polysaccharide of E. coli O2 studied earlier [Jansson et al., Carbohydr. Res. 161 (1987) 273–279], which differs in the presence of a side-chain α-d-Fucp3NAc residue. In spite of the difference between the O-polysaccharides, the corresponding genes in the O2- and O50-antigen gene cluster are 99–100% identical. The genetic basis for the lack of d-Fucp3NAc from the O50 polysaccharide is evidently a point mutation in the aminotransferase gene fdtB of the d-Fucp3NAc synthesis pathway resulting in a single amino acid change from histidine in O2 to arginine in O50.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Corrigendum to “Structure of the O-polysaccharide of Escherichia coli
           O87” [Carbohydr. Res. 412 (2015) 15–18]
    • Abstract: Publication date: 15 July 2018
      Source:Carbohydrate Research, Volume 464
      Author(s): Evelina L. Zdorovenko, Alla K. Golomidova, Nikolai S. Prokhorov, Alexander S. Shashkov, Lei Wang, Andrei V. Letarov, Yuriy A. Knirel


      PubDate: 2018-05-28T16:29:17Z
       
  • Synthesis of glyceryl glycosides related to A-type prymnesin toxins
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463
      Author(s): Edward S. Hems, Sergey A. Nepogodiev, Martin Rejzek, Robert A. Field
      A suite of glycosylated glycerol derivatives representing various fragments of the glycosylated ichthyotoxins called prymnesins were chemically synthesised. Glycerol was used to represent a small fragment of the prymnesin backbone, and was glycosylated at the 2° position with the sugars currently reported to be present on prymnesin toxins. Neighbouring group participation was utilised to synthesise 1,2-trans-glycosides. SnCl2-promoted glycosylation with furanosyl fluorides gave 1,2-cis-furanosides with moderate stereocontrol, whilst TMSOTf promoted glycosylation with a furanosyl imidate gave a 1,2-cis-furanoside with good stereocontrol. The chemical synthesis of two larger glyceryl diglycoside fragments of prymnesin-1, glycosylated with α-ʟ-arabinopyranose and α-ᴅ-ribofuranose, is also described. As the stereochemistry of the prymnesin backbones at this region is undefined, both the 2R- and 2S- glycerol isomers were synthesised. The separated diastereoisomers were distinguished by comparing NOESY NMR with computational models.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro
           inositols: Does the reaction proceed through ‘axial rich’
           conformation'
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463
      Author(s): Nitai Sarkar, Richa S. Sardessai, Mysore S. Shashidhar, Majid I. Tamboli, Rajesh G. Gonnade
      scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. This provides a potential route for the preparation of ring modified inositol derivatives. DFT calculations suggest that this epoxide formation could be proceeding through the intermediacy of the cyclohexane ring-inverted axial-rich conformer (1,2-trans-diaxial halohydrin). This is supported by the results of DFT calculations on the formation of inositol orthoformate, where the product is locked in the axial-rich conformation, while the starting inositol has the equatorial-rich conformation.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Recent advances in the synthesis of cyclic 5′-nornucleoside
           phosphonate analogues
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463
      Author(s): Guang Huan Shen, Joon Hee Hong
      Nucleoside phosphonates are isosteric, isopolar, and isoelectronic with phosphates. Nucleoside phosphonates can undergo enzymatic phosphorylation for conversion into the corresponding diphosphoryl phosphonates, which are naturally occurring nucleoside triphosphate analogues. The biological activity, which is mostly antiviral and antitumor but sometimes is as specific enzyme inhibitor, is briefly presented to help discover compounds with increased activity over natural nucleosides to provide structure-activity data. This review focuses on the synthesis of three types of cyclic 5′-nucleoside phosphonate analogues: (1) furanose 5′-nornucleoside phosphonates, (2) carbocyclic 5′-nornucleoside phosphonates, and (3) apiose 5′-nornucleoside phosphonates.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Discovery and description of a new serogroup 7 Streptococcus pneumoniae
           serotype, 7D, and structural analysis of 7C and 7D
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463
      Author(s): Christian Kjeldsen, Sofie Slott, Pernille L. Elverdal, Carmen L. Sheppard, Georgia Kapatai, Norman K. Fry, Ian C. Skovsted, Jens Ø. Duus
      Streptococcus pneumoniae is characterised into 92 serotypes based on antigenic reactions of commercial rabbit sera to the capsular polysaccharides. During development of a bioinformatic serotyping tool (PneumoCaT), an isolate exhibited a novel codon at residue 385 of the glycosyltransferase gene wcwK encoding a distinct amino acid, which differentiates genogroup 7. Investigation by repeat serotyping and Quellung reaction revealed a novel pattern of factor sera with the isolate reacting very strongly with 7f, but also with 7e factor sera. The structure of the capsular polysaccharide was determined by NMR spectroscopy to be an approximately 5:1 combination of the structures of 7C and 7B, respectively, and the structure of 7C was also elucidated. All data from whole genome sequencing, NMR spectroscopy, production of antisera and serotyping of the novel 7 strain shows that it is a new serotype, which will be named in the Danish nomenclature as 7D.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Structure of the LPS O-chain from Fusobacterium nucleatum strain MJR
           7757 B
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463
      Author(s): Evgeny Vinogradov, Frank St Michael, Andrew D. Cox
      Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. It was also found in colorectal cancer tissues and is linked with pregnancy complications, including pre-term and still births. Cell surface structures of the bacterium could be implicated in pathogenesis. Here we report the following structure of the lipopolysaccharide O-chain of F. nucleatum strain MJR 7757 B:where Lac is (R)-1-carboxyethyl (lactic acid residue); all monosaccharides are in the pyranose form. ManNAc4Lac, analogue of N-acetylmuramic acid, is found for the first time in natural sources.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Quantification of anomeric structural changes of glucose solutions using
           near-infrared spectra
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463
      Author(s): Sae Tanaka, Dušan Kojić, Roumiana Tsenkova, Masato Yasui
      Glucose is the most abundant carbohydrate found in living organisms. It exists as two anomers: α-D-glucose and β-D-glucose, which differ in how the hydroxyl group on the C1 carbon is directed. In solutions, the ratio between α- and β-D-glucose is typically 4:6 but can vary depending on the surrounding ions or temperature. In this study, we obtained near-infrared (NIR) spectra of the glucose anomers based on concentration, and analyzed the spectral difference between each anomer by spectra subtraction and principal component analysis, respectively. Moreover, by simultaneously measuring the optical rotation and NIR spectra from dissolution to equilibration, we showed that NIR spectra quantitatively estimated the specific rotations of glucose solutions using partial least-squares regression in the 1100–1800 nm wavelength range. All the analytical results indicated that the absorption at 1742 nm possess the potential to distinguish each glucose anomer quantitatively. Therefore, we addressed the prediction of the specific rotation by the absorption at 1742 nm, and demonstrated that the absorption normalized by line subtraction showed the high correlation with measured specific rotation. The absorption at 1742 nm reflects structural changes of the glucose anomers in solution. Our spectroscopy study not only provides spectral information about glucose anomers, which are the most fundamental chemical compounds in organisms, but also shows the possibility to detect the anomer ratio in vivo for the fields of agriculture and medicine by taking advantage of NIR.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463


      PubDate: 2018-05-28T16:29:17Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 30 June 2018
      Source:Carbohydrate Research, Volume 463


      PubDate: 2018-05-28T16:29:17Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462


      PubDate: 2018-05-28T16:29:17Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 15 June 2018
      Source:Carbohydrate Research, Volume 462


      PubDate: 2018-05-28T16:29:17Z
       
  • Synthesis and use of 6,6,6-trifluoro-L-fucose to block core-fucosylation
           in hybridoma cell lines
    • Abstract: Publication date: Available online 23 May 2018
      Source:Carbohydrate Research
      Author(s): Nicole C. McKenzie, Nichollas E. Scott, Alan John, Jonathan M. White, Ethan D. Goddard-Borger
      Many monoclonal antibodies (mAbs) used in cancer immunotherapy mediate tumour cell lysis by recruiting natural killer (NK) cells; a phenomenon known as antibody-dependent cellular cytotoxicity (ADCC). Eliminating core-fucose from the N-glycans of a mAb enhances its capacity to induce ADCC. As such, inhibitors of fucosylation are highly desirable for the production of mAbs for research and therapeutic use. Herein, we describe a simple synthesis of 6,6,6-trifluoro-l-fucose (F3Fuc), a metabolic inhibitor of fucosylation, and demonstrate the utility of this molecule in the production of low-fucose mAbs from murine hybridoma cell lines.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • Structural studies on the O-polysaccharide of Escherichia coli O57
    • Abstract: Publication date: Available online 19 May 2018
      Source:Carbohydrate Research
      Author(s): Olesya I. Naumenko, Jingjie Song, Sof'ya N. Senchenkova, Xiaohan Jiang, Andrei V. Perepelov, Alexander S. Shashkov, Yuriy A. Knirel
      Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O57 afforded an O-polysaccharide, which was isolated by gel permeation chromatography (GPC) and studied by sugar analysis, Smith degradation and solvolysis with trifluoroacetic acid, along with 2D 1H and 13C NMR spectroscopy. The O-polysaccharide was found to contain d-Glc, d-Gal, d-GalA, d-GlcNAc, and l-FucNAc, as well as O-acetyl groups. Smith degradation of the O-deacetylated polysaccharide destroyed side-branch β-Gl≿p and α-GalpA to give a modified linear polysaccharide. Solvolysis cleaved selectively the linkage of α-l-FucpNAc to give a pentasaccharide corresponding to the O-polysaccharide repeat. A comparison of the NMR spectra of the initial and O-deacetylated polysaccharides showed that α-GalpA is non-stoichiometrically O-acetylated at position either 2 (∼30%) or 3 (∼40%). The following structure of the O-polysaccharide was established, which is unique among known bacterial polysaccharide structures: Image 2
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • MCAW-DB: A glycan profile database capturing the ambiguity of glycan
           recognition patterns
    • Abstract: Publication date: Available online 11 May 2018
      Source:Carbohydrate Research
      Author(s): Masae Hosoda, Yushi Takahashi, Masaaki Shiota, Daisuke Shinmachi, Renji Inomoto, Shinichi Higashimoto, Kiyoko F. Aoki-Kinoshita
      Glycan-binding protein (GBP) interaction experiments, such as glycan microarrays, are often used to understand glycan recognition patterns. However, oftentimes the interpretation of glycan array experimental data makes it difficult to identify discrete GBP binding patterns due to their ambiguity. It is known that lectins, for example, are non-specific in their binding affinities; the same lectin can bind to different monosaccharides or even different glycan structures. In bioinformatics, several tools to mine the data generated from these sorts of experiments have been developed. These tools take a library of predefined motifs, which are commonly-found glycan patterns such as sialyl-Lewis X, and attempt to identify the motif(s) that are specific to the GBP being analyzed. In our previous work, as opposed to using predefined motifs, we developed the Multiple Carbohydrate Alignment with Weights (MCAW) tool to visualize the state of the glycans being recognized by the GBP under analysis. We previously reported on the effectiveness of our tool and algorithm by analyzing several glycan array datasets from the Consortium of Functional Glycomics (CFG). In this work, we report on our analysis of 1081 data sets which we collected from the CFG, the results of which we have made publicly and freely available as a database called MCAW-DB. We introduce this database, its usage and describe several analysis results. We show how MCAW-DB can be used to analyze glycan-binding patterns of GBPs amidst their ambiguity. For example, the visualization of glycan-binding patterns in MCAW-DB show how they correlate with the concentrations of the samples used in the array experiments. Using MCAW-DB, the patterns of glycans found to bind to various GBP-glycan binding proteins are visualized, indicating the binding “environment” of the glycans. Thus, the ambiguity of glycan recognition is numerically represented, along with the patterns of monosaccharides surrounding the binding region. The profiles in MCAW-DB could potentially be used as predictors of affinity of unknown or novel glycans to particular GBPs by comparing how well they match the existing profiles for those GBPs. Moreover, as the glycan profiles of diseased tissues become available, glycan alignments could also be used to identify glycan biomarkers unique to that tissue. Databases of these alignments may be of great use for drug discovery.
      Graphical abstract image

      PubDate: 2018-05-28T16:29:17Z
       
  • 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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