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  Subjects -> CHEMISTRY (Total: 846 journals)
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    - CHEMISTRY (597 journals)
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CHEMISTRY (597 journals)                  1 2 3 | Last

Showing 1 - 200 of 735 Journals sorted alphabetically
2D Materials     Hybrid Journal   (Followers: 5)
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: 23)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 15)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 24)
ACS Macro Letters     Full-text available via subscription   (Followers: 18)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 31)
ACS Nano     Full-text available via subscription   (Followers: 156)
ACS Photonics     Full-text available via subscription   (Followers: 6)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 16)
Acta Chemica Iasi     Open Access  
Acta Chimica Sinica     Full-text available via subscription   (Followers: 1)
Acta Chimica Slovaca     Open Access   (Followers: 2)
Acta Chromatographica     Full-text available via subscription   (Followers: 8)
Acta Facultatis Medicae Naissensis     Open Access  
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 4)
Acta Scientifica Naturalis     Open Access  
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 5)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 5)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 4)
Advanced Functional Materials     Hybrid Journal   (Followers: 41)
Advanced Science Focus     Free   (Followers: 2)
Advances in Chemical Engineering and Science     Open Access   (Followers: 33)
Advances in Chemical Science     Open Access   (Followers: 10)
Advances in Chemistry     Open Access   (Followers: 7)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 14)
Advances in Drug Research     Full-text available via subscription   (Followers: 21)
Advances in Environmental Chemistry     Open Access   (Followers: 1)
Advances in Enzyme Research     Open Access   (Followers: 4)
Advances in Fluorine Science     Full-text available via subscription   (Followers: 8)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 12)
Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 8)
Advances in Materials Physics and Chemistry     Open Access   (Followers: 15)
Advances in Nanoparticles     Open Access   (Followers: 12)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 13)
Advances in Polymer Science     Hybrid Journal   (Followers: 36)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 13)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 13)
Advances in Quantum Chemistry     Full-text available via subscription   (Followers: 5)
Advances in Science and Technology     Full-text available via subscription   (Followers: 2)
African Journal of Bacteriology Research     Open Access  
African Journal of Chemical Education     Open Access   (Followers: 2)
African Journal of Pure and Applied Chemistry     Open Access   (Followers: 6)
Agrokémia és Talajtan     Full-text available via subscription   (Followers: 2)
Alkaloids: Chemical and Biological Perspectives     Full-text available via subscription   (Followers: 3)
AMB Express     Open Access   (Followers: 1)
Ambix     Hybrid Journal   (Followers: 3)
American Journal of Biochemistry and Biotechnology     Open Access   (Followers: 68)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 12)
American Journal of Chemistry     Open Access   (Followers: 23)
American Journal of Plant Physiology     Open Access   (Followers: 13)
American Mineralogist     Full-text available via subscription   (Followers: 7)
Anadolu University Journal of Science and Technology     Open Access  
Analyst     Full-text available via subscription   (Followers: 41)
Angewandte Chemie     Hybrid Journal   (Followers: 115)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 163)
Annales UMCS, Chemia     Open Access   (Followers: 1)
Annals of Clinical Chemistry and Laboratory Medicine     Open Access   (Followers: 1)
Annual Reports in Computational Chemistry     Full-text available via subscription   (Followers: 2)
Annual Reports Section A (Inorganic Chemistry)     Full-text available via subscription   (Followers: 3)
Annual Reports Section B (Organic Chemistry)     Full-text available via subscription   (Followers: 7)
Annual Review of Chemical and Biomolecular Engineering     Full-text available via subscription   (Followers: 8)
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     Full-text available via subscription  
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 5)
Applied Spectroscopy     Full-text available via subscription   (Followers: 22)
Applied Surface Science     Hybrid Journal   (Followers: 20)
Arabian Journal of Chemistry     Open Access   (Followers: 6)
ARKIVOC     Open Access   (Followers: 2)
Asian Journal of Biochemistry     Open Access   (Followers: 1)
Atomization and Sprays     Full-text available via subscription   (Followers: 2)
Australian Journal of Chemistry     Hybrid Journal   (Followers: 4)
Autophagy     Hybrid Journal   (Followers: 2)
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 8)
Biochemistry     Full-text available via subscription   (Followers: 204)
Biochemistry Insights     Open Access   (Followers: 4)
Biochemistry Research International     Open Access   (Followers: 4)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 8)
Bioinspired Materials     Open Access   (Followers: 2)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 1)
Biointerphases     Open Access   (Followers: 1)
Biology, Medicine, & Natural Product Chemistry     Open Access  
Biomacromolecules     Full-text available via subscription   (Followers: 17)
Biomass Conversion and Biorefinery     Partially Free   (Followers: 9)
Biomedical Chromatography     Hybrid Journal   (Followers: 7)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 2)
BioNanoScience     Partially Free   (Followers: 4)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 94)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 84)
Bioorganic Chemistry     Hybrid Journal   (Followers: 9)
Biopolymers     Hybrid Journal   (Followers: 16)
Biosensors     Open Access   (Followers: 1)
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: 3)
Bulletin of the Chemical Society of Japan     Full-text available via subscription   (Followers: 24)
Bulletin of the Korean Chemical Society     Hybrid Journal  
C - Journal of Carbon Research     Open Access   (Followers: 2)
Canadian Association of Radiologists Journal     Full-text available via subscription   (Followers: 2)
Canadian Journal of Chemistry     Full-text available via subscription   (Followers: 6)
Canadian Mineralogist     Full-text available via subscription   (Followers: 3)
Carbohydrate Research     Hybrid Journal   (Followers: 27)
Carbon     Hybrid Journal   (Followers: 64)
Catalysis for Sustainable Energy     Open Access   (Followers: 4)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 6)
Catalysis Science and Technology     Free   (Followers: 4)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 3)
Catalysts     Open Access   (Followers: 5)
Cellulose     Hybrid Journal   (Followers: 4)
Cereal Chemistry     Full-text available via subscription   (Followers: 4)
ChemBioEng Reviews     Full-text available via subscription  
ChemCatChem     Hybrid Journal   (Followers: 5)
Chemical and Engineering News     Free   (Followers: 10)
Chemical Bulletin of Kazakh National University     Open Access  
Chemical Communications     Full-text available via subscription   (Followers: 62)
Chemical Engineering Research and Design     Hybrid Journal   (Followers: 20)
Chemical Research in Chinese Universities     Hybrid Journal   (Followers: 3)
Chemical Research in Toxicology     Full-text available via subscription   (Followers: 17)
Chemical Reviews     Full-text available via subscription   (Followers: 136)
Chemical Science     Open Access   (Followers: 18)
Chemical Technology     Open Access   (Followers: 5)
Chemical Vapor Deposition     Hybrid Journal   (Followers: 4)
Chemical Week     Full-text available via subscription   (Followers: 7)
Chemie in Unserer Zeit     Hybrid Journal   (Followers: 53)
Chemie-Ingenieur-Technik (Cit)     Hybrid Journal   (Followers: 26)
ChemInform     Hybrid Journal   (Followers: 4)
Chemistry & Biodiversity     Hybrid Journal   (Followers: 5)
Chemistry & Biology     Full-text available via subscription   (Followers: 30)
Chemistry & Industry     Hybrid Journal   (Followers: 2)
Chemistry - A European Journal     Hybrid Journal   (Followers: 109)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 12)
Chemistry and Materials Research     Open Access   (Followers: 14)
Chemistry Central Journal     Open Access   (Followers: 5)
Chemistry Education Research and Practice     Free   (Followers: 4)
Chemistry in Education     Open Access   (Followers: 2)
Chemistry International     Hybrid Journal   (Followers: 1)
Chemistry Letters     Full-text available via subscription   (Followers: 41)
Chemistry of Materials     Full-text available via subscription   (Followers: 137)
Chemistry of Natural Compounds     Hybrid Journal   (Followers: 8)
Chemistry World     Full-text available via subscription   (Followers: 21)
Chemistry-Didactics-Ecology-Metrology     Open Access  
ChemistryOpen     Open Access   (Followers: 1)
Chemkon - Chemie Konkret, Forum Fuer Unterricht Und Didaktik     Hybrid Journal  
Chemoecology     Hybrid Journal   (Followers: 2)
Chemometrics and Intelligent Laboratory Systems     Hybrid Journal   (Followers: 15)
Chemosensors     Open Access  
ChemPhysChem     Hybrid Journal   (Followers: 6)
ChemTexts     Hybrid Journal  
CHIMIA International Journal for Chemistry     Full-text available via subscription   (Followers: 3)
Chinese Journal of Chemistry     Hybrid Journal   (Followers: 6)
Chinese Journal of Polymer Science     Hybrid Journal   (Followers: 10)
Chromatographia     Hybrid Journal   (Followers: 25)
Chromatography     Open Access   (Followers: 5)
Chromatography Research International     Open Access   (Followers: 5)
Clay Minerals     Full-text available via subscription   (Followers: 9)
Cogent Chemistry     Open Access  
Colloid and Interface Science Communications     Open Access  
Colloid and Polymer Science     Hybrid Journal   (Followers: 8)
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: 17)
Comments on Inorganic Chemistry: A Journal of Critical Discussion of the Current Literature     Hybrid Journal   (Followers: 1)
Composite Interfaces     Hybrid Journal   (Followers: 3)
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: 10)
Computational Biology and Chemistry     Hybrid Journal   (Followers: 10)
Computational Chemistry     Open Access   (Followers: 2)
Computers & Chemical Engineering     Hybrid Journal   (Followers: 9)
Coordination Chemistry Reviews     Full-text available via subscription  
Copernican Letters     Open Access  
Critical Reviews in Biochemistry and Molecular Biology     Hybrid Journal   (Followers: 4)
Crystal Structure Theory and Applications     Open Access   (Followers: 2)
CrystEngComm     Full-text available via subscription   (Followers: 6)
Current Catalysis     Hybrid Journal   (Followers: 1)
Current Metabolomics     Hybrid Journal   (Followers: 3)
Current Opinion in Colloid & Interface Science     Hybrid Journal   (Followers: 7)
Current Opinion in Molecular Therapeutics     Full-text available via subscription   (Followers: 16)
Current Research in Chemistry     Open Access   (Followers: 7)
Current Science     Open Access   (Followers: 11)
Dalton Transactions     Full-text available via subscription   (Followers: 17)
Detection     Open Access   (Followers: 2)
Developments in Geochemistry     Full-text available via subscription   (Followers: 1)
Diamond and Related Materials     Hybrid Journal   (Followers: 12)
Dislocations in Solids     Full-text available via subscription  
Doklady Chemistry     Hybrid Journal  
Drying Technology: An International Journal     Hybrid Journal   (Followers: 3)
Eclética Química     Open Access   (Followers: 1)
Ecological Chemistry and Engineering S     Open Access   (Followers: 2)
Ecotoxicology and Environmental Contamination     Open Access  
Educación Química     Open Access   (Followers: 1)
Education for Chemical Engineers     Hybrid Journal   (Followers: 4)
Elements     Full-text available via subscription  
Environmental Chemistry     Hybrid Journal   (Followers: 5)
Environmental Chemistry Letters     Hybrid Journal   (Followers: 2)

        1 2 3 | Last

Journal Cover Carbohydrate Research
  [SJR: 0.654]   [H-I: 83]   [27 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
   Published by Elsevier Homepage  [2970 journals]
  • Reduction of sugar lactones to hemiacetals with lithium
           triethylborohydride
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Cesar Gonzalez, Sam Kavoosi, Andersson Sanchez, Stanislaw F. Wnuk
      Reduction of ribono-1,4-lactones and gulono-1,4-lactone as well as ribono-1,5-lactone and glucono-1,5-lactones with LTBH (1.2 equiv.) in CH2Cl2 at 0 °C for 30 min provided the corresponding pentose or hexose hemiacetals in high yields. Commonly used in carbohydrate chemistry protecting groups such as trityl, benzyl, silyl, acetals and to some extent acyls are compatible with this reduction.
      Graphical abstract image

      PubDate: 2016-06-23T14:53:40Z
       
  • A one-pot synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by
           hydrodeoxygenation of xylose using a palladium catalyst
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Michael A. Jackson, Judith A. Blackburn, Neil P.J. Price, Karl E. Vermillion, Steven C. Peterson, Gregory M. Ferrence
      In an effort to expand the number of biobased chemicals available from sugars, xylose has been converted to 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane in a one-pot reaction using palladium supported on silica-alumina as the catalyst. The title compound is produced in 35–40% yield under 7 MPa H2 pressure at 733 K using 3–10 wt%Pd on silica-alumina catalyst. It is isolated using a combination of liquid-liquid extractions and flash chromatography. This dimer can be converted to its monomer, 2-hydroxy-(2-hydroxymethyl)tetrahydrofuran, which ring opens under acid conditions to 1,5-dihydroxy-2-pentanone. This diol can then be esterified with vinylacetate in phosphate buffer to produce 1,5-bis(acetyloxy)-2-pentanone which is an inhibitor of mammalian 11β-hydroxysteroid dehydrogenase 1. 1H and 13C nmr spectra of each of these species are reported. The single crystal X-ray structure of the title compound is also reported. These data were collected in a temperature range of 100 K–273 K and show a solid state phase change from triclinic to monoclinic between 175 K and 220 K without a conformational change.
      Graphical abstract image

      PubDate: 2016-06-23T14:53:40Z
       
  • An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones
           upon hydrogenolysis of the anomeric benzyl group
    • Abstract: Publication date: Available online 18 June 2016
      Source:Carbohydrate Research
      Author(s): Shenyou Nie, Xiaoping Chen, Yuyong Ma, Wei Li, Biao Yu
      During our synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.
      Graphical abstract image

      PubDate: 2016-06-18T12:40:13Z
       
  • Comprehensive analysis of the N-glycan biosynthetic pathway using
           bioinformatics to generate UniCorn: A theoretical N-glycan structure
           database
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Yukie Akune, Chi-Hung Lin, Jodie L. Abrahams, Jingyu Zhang, Nicolle H. Packer, Kiyoko F. Aoki-Kinoshita, Matthew P. Campbell
      Glycan structures attached to proteins are comprised of diverse monosaccharide sequences and linkages that are produced from precursor nucleotide-sugars by a series of glycosyltransferases. Databases of these structures are an essential resource for the interpretation of analytical data and the development of bioinformatics tools. However, with no template to predict what structures are possible the human glycan structure databases are incomplete and rely heavily on the curation of published, experimentally determined, glycan structure data. In this work, a library of 45 human glycosyltransferases was used to generate a theoretical database of N-glycan structures comprised of 15 or less monosaccharide residues. Enzyme specificities were sourced from major online databases including Kyoto Encyclopedia of Genes and Genomes (KEGG) Glycan, Consortium for Functional Glycomics (CFG), Carbohydrate-Active enZymes (CAZy), GlycoGene DataBase (GGDB) and BRENDA. Based on the known activities, more than 1.1 million theoretical structures and 4.7 million synthetic reactions were generated and stored in our database called UniCorn. Furthermore, we analyzed the differences between the predicted glycan structures in UniCorn and those contained in UniCarbKB (www.unicarbkb.org), a database which stores experimentally described glycan structures reported in the literature, and demonstrate that UniCorn can be used to aid in the assignment of ambiguous structures whilst also serving as a discovery database.
      Graphical abstract image

      PubDate: 2016-06-18T12:40:13Z
       
  • A β-agarase with high pH stability from Flammeovirga sp. SJP92
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Qi Dong, Lingwei Ruan, Hong Shi
      A novel endo-type β-agarase, AgaB, was cloned from an agar-degrading bacterium, Flammeovirga sp. SJP92. The gene agaB consists of 2, 550 bp and encodes a protein of 849 amino acids including a 19 amino acids signal peptide. Based on the amino acid sequence similarity, AgaB belongs to the glycoside hydrolase family GH16. The recombinant AgaB was expressed in Escherichia coli and exhibited maximal activity at around 45 °C and pH 8.0, with a specific activity of 254.2 U/mg, a K m of 3.99 mg/ml and a V max of 700 U/mg for agarose. The agarase was stable at neutral to mildly alkaline condition, and remained 85%–90% of activity after treatment for 1 h, a characteristic much more different from other agarases reported. The recombinant enzyme was sensitive to some metal ions (Cu2+, Co2+ and Zn2+), but resistant to some denaturants (urea and SDS). It can hydrolyze the β-1, 4-glycosidic linkages of agarose, yielding neoagarotetraose and neoagarohexaose as the main products. These properties could make AgaB has a potential application in the food, cosmetic and medical industries.
      Graphical abstract image

      PubDate: 2016-06-18T12:40:13Z
       
  • The comparison of glycosphingolipids isolated from an epithelial ovarian
           cancer cell line and a nontumorigenic epithelial ovarian cell line using
           MALDI-MS and MALDI-MS/MS
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Krishani K. Rajanayake, William R. Taylor, Dragan Isailovic
      Glycosphingolipids (GSLs) are important biomolecules, which are linked to many diseases such as GSL storage disorders and cancer. Consequently, the expression of GSLs may be altered in ovarian cancer cell lines in comparison to apparently healthy cell lines. Here, differential expressions of GSLs in an epithelial ovarian cancer cell line SKOV3 and a nontumorigenic epithelial ovarian cell line T29 were studied using matrix-assisted laser desorption/ionization-mass spectrometry (MALDI-MS) and MALDI-MS/MS. The isolation of GSLs from SKOV3 and T29 cell lines was carried out using Folch partition. GSLs were successfully detected by MALDI-MS, and structurally assigned by a comparison of their MALDI-MS/MS fragmentation patterns with MS/MS data found in SimLipid database. Additionally, LIPID MAPS was used to assign GSL ion masses in MALDI-MS spectra. Seventeen neutral GSLs were identified in Folch partition lower (chloroform/methanol) phases originating from both cell lines, while five globo series neutral GSLs were identified only in the Folch partition lower phase of SKOV3 cell line. Several different sialylated GSLs were detected in Folch partition upper (water/methanol) phases of SKOV3 and T29 cell lines. Overall, this study demonstrates the alteration and increased glycosylation of GSLs in an epithelial ovarian cancer cell line in comparison to a nontumorigenic epithelial ovarian cell line.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Rapid synthesis of linear homologous oligoarabinofuranosides related to
           mycobacterial lipoarabinomannan and a neoglycoconjugate thereof
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Nikita M. Podvalnyy, Alexander O. Chizhov, Alexander I. Zinin, Leonid O. Kononov
      Rapid and simple synthesis of oligosaccharides related to one of the terminal motifs of mycobacterial lipoarabinomannan is described. An array of homologous linear α(1 → 5)-linked oligoarabinofuranosides with 4-(2-chloroethoxy)phenyl aglycon and selectively unprotected 5-OH group at the non-reducing end was obtained by oligomerization of 3-O-benzoyl β-D-arabinofuranose 1,2,5-orthobenzoate. Subsequent introduction of β(1 → 2)-linked arabinofuranose disaccharide moiety by step-wise glycosylation furnished the target oligosaccharides which were conjugated with bovine serum albumin.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthetic multivalent ligands for cholera & cholera-like toxins:
           Protected cyclic neoglycopeptides
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Vajinder Kumar, Narender Yadav, K.P. Ravindranathan Kartha
      Synthesis of a set of novel glycopeptide analogues as potential cholera/cholera-like toxin inhibitors in their protected form is described. They include di-, tri-, tetra- and pentavalent scaffolds. The synthetic steps were achieved using a combination of solvent-free mechanochemical as well as the conventional solution-phase reactions. During the conventional DIC-HOBt-mediated peptide coupling followed for the preparation of certain glycopeptide analogues an interesting in situ Fmoc deprotection was observed which has been demonstrated to hold potential for synthesiszing glycopeptides/neoglycopeptides with extended polyamide chains.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Structural and binding properties of laminarin revealed by analytical
           ultracentrifugation and calorimetric analyses
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Masayuki Oda, Yoichi Tanabe, Masanori Noda, Satomi Inaba, Elena Krayukhina, Harumi Fukada, Susumu Uchiyama
      One of the β-1,3-glucans, laminarin, has been widely used as a substrate for enzymes including endo-1,3-β-glucanase. To obtain quantitative information about the molecular interaction between laminarin and endo-1,3-β-glucanase, the structural properties of laminarin should be determined. The results from pioneering work using analytical ultracentrifugation for carbohydrate analysis showed that laminarin from Laminaria digitata predominantly exists as a single-chain species with approximately 5% of triple-helical species. Differential scanning calorimetry experiments did not show a peak assignable to the transition from triple-helix to single-chain, supporting the notion that a large proportion of laminarin is the single-chain species. The interaction of laminarin with an inactive variant of endo-1,3-β-glucanase from Cellulosimicrobium cellulans, E119A, was quantitatively analyzed using isothermal titration calorimetry. The binding was enthalpically driven and the binding affinity was approximately 106 M−1. The results from binding stoichiometric analysis indicated that on average, E119A binds to laminarin in a 2:1 ratio. This seems to be reasonable, because laminarin mainly exists as a monomer, the apparent molecular mass of laminarin is 3.6 kDa, and E119A would have substrate-binding subsites corresponding to 6 glucose units. The analytical ultracentrifugation experiments could detect different complex species of laminarin and endo-1,3-β-glucanase.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Graphical contents list
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430




      PubDate: 2016-06-15T11:05:10Z
       
  • Functionalized β-cyclodextrin as supramolecular ligand and their
           Pd(OAc)2 complex: highly efficient and reusable catalyst for
           Mizoroki–Heck cross-coupling reactions in aqueous medium
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Someshwar D. Dindulkar, Daham Jeong, Hwanhee Kim, Seunho Jung
      A novel class of water soluble palladium complexes with recognition abilities based on functionalized β-cyclodextrin has been synthesized. The complex demonstrated high catalytic activity and a supramolecular platform for phosphine-free Mizoroki–Heck cross-coupling reactions in water. The efficient arylation of alkenes was carried out using different iodo- and bromo-arenes with good to excellent yields (up to 96%). The advantages, like recyclability of catalysts, operational simplicity and accessibility in aqueous medium, make this protocol eco-friendly.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Editorial board
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430




      PubDate: 2016-06-15T11:05:10Z
       
  • Structural characterization of the O-polysaccharide isolated from
           Franconibacter helveticus LMG23732T
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Sylwia Szulta, Małgorzata Czerwicka, Stephen J. Forsythe, Karolina Ossowska, Halina Dziadziuszko, Zbigniew Kaczyński
      The bacterial strain Franconibacter helveticus LMG 23732T was previously misidentified as the neonatal pathogen Cronobacter zurichensis. O-polysaccharide (OPS) is a part of lipopolysaccharide (LPS), which is an important cell envelope compound of Gram-negative bacteria. OPS isolated from the bacterium Franconibacter helveticus LMG23732T was characterized by chemical analyses as well as 1D and 2D NMR experiments. Compositional analyses indicated the presence of glucose and unusual 6-deoxy sugar - 6-deoxy-talose (6-dTal). The studied strain produced OPS, which consists of 6-l-dTalp in main chain and terminal d-Glcp as a branch: This is the first structural determination of the OPS isolated from genus Franconibacter.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • An efficient method for the synthesis of pyranoid glycals
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Heshan Chen, Ting Xian, Wan Zhang, Wenshuai Si, Xiaosheng Luo, Bo Zhang, Meiyu Zhang, Zhongfu Wang, Jianbo Zhang
      A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30–60 °C. The corresponding glycals were obtained with excellent isolated yields (72–96%) in a short time (20–50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis and antituberculosis activity of the first macrocyclic
           glycoterpenoids comprising glucosamine and diterpenoid isosteviol
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Bulat F. Garifullin, Irina Yu. Strobykina, Radmila R. Sharipova, Marionella A. Kravchenko, Olga V. Andreeva, Olga B. Bazanova, Vladimir E. Kataev
      The first macrocyclic glycoterpenoids comprising glucosamine and diterpenoid isosteviol moieties were synthesized and evaluated for inhibition activity against Mycobacterium tuberculosis H37Rv.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Editorial board
    • Abstract: Publication date: 16 June 2016
      Source:Carbohydrate Research, Volume 428




      PubDate: 2016-06-15T11:05:10Z
       
  • Voglibose-inspired synthesis of new potent α-glucosidase inhibitors
           N-1,3-dihydroxypropylaminocyclitols
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Wisuttaya Worawalai, Pornthep Sompornpisut, Sumrit Wacharasindhu, Preecha Phuwapraisirisan
      Voglibose, an N-1,3-dihydroxypropylaminocyclitol, has widely been used as an effective α-glucosidase inhibitor for diabetes therapy. Several attempts have been made to synthesize closely related analogues through the coupling of various aminocyclitols and propane-1,3-diol; however, most of them showed weaker or no inhibition. In this communication, we synthesized a pair of new N-1,3-dihydroxypropylaminocyclitols (10 and 11) using (+)-proto-quercitol (1) as a cyclitol core structure. The newly synthesized compounds revealed potent rat intestinal α-glucosidases, particularly against maltase, with IC50 values at submicromolar. Subsequent study on mechanisms underlying the inhibition of 11 indicated the competitive manner towards maltase and sucrase. The potent inhibition of these compounds was elaborated by docking study, in which their binding profiles towards key amino acid residues in the active site were similar to that of voglibose. Therefore, introduction of propane-1,3-diol moiety to suitable cyclohexane core structure such as aminoquercitol would be a potential approach to discover a new series of effective α-glucosidase inhibitors.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • A ring closing metathesis strategy for carbapyranosides of xylose and
           arabinose
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Clayton E. Mattis, David R. Mootoo
      The synthesis of β-carba-xylo and arabino pyranosides of cholestanol is described. The synthetic strategy, which is analogous to the Postema approach to C-glycosides, centers on the ring closing metathesis of an enol ether–alkene precursor to give a cyclic enol ether that is elaborated to a carba-pyranoside via hydroboration–oxidation on the olefin. The method, which is attractive for its modularity and stereoselectivity, may find wider applications to carba-hexopyranosides and other complex cycloalkyl ether frameworks.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Design, synthesis and bioactivity evaluation of Galf mimics as
           antitubercular agents
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Chunyan Liu, Linyu Hou, Aiguo Meng, Gang Han, Weiguo Zhang, Shende Jiang
      A series of novel Galf mimics has been synthesized and characterized by IR, 1H NMR, 13C NMR, mass spectral and element analysis. All the newly prepared compounds were screened for their antitubercular activities. Bioactivity assays manifested that most of Galf mimics exhibited good antitubercular activities. Especially compound 4d and 4e displayed remarkable antitubercular efficacies, which were comparable to ethambutol.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • C-Glucopyranosyl-1,2,4-triazol-5-ones: synthesis and inhibition of
           glycogen phosphorylase
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Éva Bokor, Zsolt Széles, Tibor Docsa, Pál Gergely, László Somsák
      Various C-glucopyranosyl-1,2,4-triazolones were designed as potential inhibitors of glycogen phosphorylase. Syntheses of these compounds were performed with O-perbenzoylated glucose derivatives as precursors. High temperature ring closure of N1 -carbamoyl-C-β-D-glucopyranosyl formamidrazone gave 3-β-D-glucopyranosyl-1,2,4-triazol-5-one. Reaction of N1 -tosyl-C-β-D-glucopyranosyl formamidrazone with ClCOOEt furnished 3-β-D-glucopyranosyl-1-tosyl-1,2,4-triazol-5-one. In situ prepared β-D-glucopyranosylcarbonyl isocyanate was transformed by PhNHNHBoc into 3-β-D-glucopyranosyl-1-phenyl-1,2,4-triazol-5-one, while the analogous 1-(2-naphthyl) derivative was obtained from the unsubstituted triazolone by naphthalene-2-boronic acid in a Cu(II) catalyzed N-arylation. Test compounds were prepared by Zemplén deacylation. The new glucose derivatives had weak or no inhibition of rabbit muscle glycogen phosphorylase b: the best inhibitor was 3-β-D-glucopyranosyl-1-(2-naphthyl)-1,2,4-triazol-5-one (Ki = 80 µM).
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Evaluation of monovalent and multivalent iminosugars to modulate Candida
           albicans β-1,2-mannosyltransferase activities
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Thomas Hurtaux, Ghenima Sfihi-Loualia, Yoan Brissonnet, Julie Bouckaert, Jean-Maurice Mallet, Boualem Sendid, Florence Delplace, Emeline Fabre, Sébastien G. Gouin, Yann Guérardel
      β-1,2-Linked oligomannosides substitute the cell wall of numerous yeast species. Several of those including Candida albicans may cause severe infections associated with high rates of morbidity and mortality, especially in immunocompromised patients. β-1,2-Mannosides are known to be involved in the pathogenic process and to elicit an immune response from the host. In C. albicans, the synthesis of β-mannosides is under the control of a family of nine genes coding for putative β-mannosyltransferases. Two of them, CaBmt1 and CaBmt3, have been shown to initiate and prime the elongation of the β-mannosides on the cell-wall mannan core. In the present study, we have assessed the modulating activities of monovalent and multivalent iminosugar analogs on these enzymes in order to control the enzymatic bio-synthesis of β-mannosides. We have identified a monovalent deoxynojirimycin (DNJ) derivative that inhibits the CaBmt1-catalyzed initiating activity, and mono-, tetra- and polyvalent deoxymannojirimycin (DMJ) that modulate the CaBmt1 activity toward the formation of a single major product. Analysis of the aggregating properties of the multivalent iminosugars showed their ability to elicit clusterization of both CaBmt1 and CaBmt3, without affecting their activity. These results suggest promising roles for multivalent iminosugars as controlling agents for the biosynthesis of β-1,2 mannosides and for monovalent DNJ derivative as a first target for the design of future β-mannosyltransferase inhibitors.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Influence of the configurational pattern of sp2-iminosugar pseudo N-, S-,
           O- and C-glycosides on their glycoside inhibitory and antitumor properties
           
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Elena M. Sánchez-Fernández, Rita Gonçalves-Pereira, Rocío Rísquez-Cuadro, Gabriela B. Plata, José M. Padrón, José M. García Fernández, Carmen Ortiz Mellet
      The synthesis of a complete series of cyclic carbamate-type sp2-iminosugar N-, S-, O- and C-octyl pseudoglycosides related to nojirimycin, mannojirimycin and galactonojirimycin, all having the α-pseudoanomeric configuration, is reported. The gem-diamine-type N-pseudoglycosides can be accessed directly from the corresponding reducing sp2-imisosugar precursors by reaction with octylamine in methanol, whereas per-O-acetyl or 1-fluoro derivatives were used as pseudoglycosyl donors for the preparation of S-pseudoglycosides or O- and C-pseudoglycosides, respectively. Evaluation of their inhibitory properties against a panel of glycosidases evidenced selectivity profiles that strongly depend on the configurational pattern and the nature of the glycosidic linkage. On the contrary, the antiproliferative activity determined against a panel of tumor cell lines was largely independent of the relative orientation of the hydroxyl groups in the sp2-iminosugar moiety. Indeed, sp2-iminosugar representatives exhibiting significant growth inhibition potencies were identified in all three configurationally different types of compounds studied, namely α-d-gluco, α-d-manno and α-d-galacto glycoside analogs. Interestingly, none of the compounds affected viability and mortality of normal cells at the used concentrations. Altogether, the results strongly suggest that the anticancer activity of amphiphilic sp2-iminosugar glycosides might be unrelated, or not solely related, to their glycosidase inhibitory activity.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis of seven-membered iminosugars fused thiazolidin-4-one and
           benzthiazinan-4-one and their HIV-RT inhibitory activity
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Yuheng Hou, Shunkai Xing, Jie Shao, Zhuqing Yin, Le Hao, Tianyu Yang, Hongzhi Zhang, Mo Zhu, Hua Chen, Xiaoliu Li
      Novel seven-membered iminosugars fused thiazolidin-4-one and benzthiazinan-4-one were conveniently synthesized by the tandem Staudinger/aza-Wittig/cyclization reaction under microwave radiation. Benzoyl group (Bz) migrations were found in the synthesis of 8c and 9b using D-galactoside or D-mannoside as starting materials, respectively, which was suggested by HMBC and X-ray. The new bi/tricyclic iminosugars 3~4(a–d) and 5(b–d) were examined for their HIV reverse transcriptase (RT) inhibitory activities. The result showed that all compounds except 5b could effectively inhibit RT activity. Among them, compounds 3c and 4c were the best ones with the IC50 values of RT inhibitory activities of 2.11 µM and 2.73 µM, respectively. Structure–activity relationship analysis suggested that the phenyl group in the tricyclic azasugars was beneficial for their anti-HIV RT activity.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Investigation of original multivalent iminosugars as pharmacological
           chaperones for the treatment of Gaucher disease
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Eugénie Laigre, Damien Hazelard, Josefina Casas, Jenny Serra-Vinardell, Helen Michelakakis, Irene Mavridou, Johannes M.F.G. Aerts, Antonio Delgado, Philippe Compain
      Multivalent iminosugars conjugated with a morpholine moiety and/or designed as prodrugs have been prepared and evaluated as new classes of pharmacological chaperones for the treatment of Gaucher disease. This study further confirms the interest of the prodrug concept and shows that the addition of a lysosome-targeting morpholine unit into iminosugar cluster structures has no significant impact on the chaperone activity on Gaucher cells.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Molecular basis for the affinity and specificity in the binding of
           five-membered iminocyclitols with glycosidases: an experimental and
           theoretical synergy
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Ashutosh Shandilya, Muthupandian Ganesan, Firdaus Parveen, Namakkal G. Ramesh, B. Jayaram
      An unusual substituent dictated complementarity in the inhibition of amino-modified five-membered iminocyclitols toward various glycosidases was reported by us. These intriguing results encouraged us to seek a molecular level explanation for the observation that may facilitate the design of specific iminocyclitol inhibitors against glycosidases of choice. We present here a detailed theoretical account that is substantiated with some new experimental investigations on the molecular origins of the differential affinities of iminocyclitols with various glycosidases. The studies involve docking/scoring, molecular dynamics simulations followed by syntheses of a few novel five-membered iminocyclitols and their in vitro binding assays. Directional hydrogen bonds and snug fit of the ligands are implicated as contributory to the observed selectivities. The observed synergy between the computations and experiment is likely to spur further research in the design of novel iminocyclitols with specific inhibitory activities.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis and evaluation of a water-solubility glycosyl-rhodamine
           fluorescent probe detecting Hg2+
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Zhengjun Chen, Wei Hu, Mian Wang, Lisheng Wang, Guifa Su, Jianyi Wang
      A glycosyl-rhodamine fluorescent probe with good water-solubility has been designed and synthesized through click reaction. Compared with control compound 1, the obtained target compound (RBGlc-3) could be independently applied for the detection of Hg2+ in water medium, and not disturbed by Ce3+, Eu3+, Ca2+, Cd2+, Fe2+, Ba2+, Co2+, Cu2+, Zn2+, Pb2+, Mg2+, Ni2+, K+, Ag+, Na+, NH4 +, CH3COO−, S2O4 2−, SO4 2−, SO3 2− and Cl−. 1:1 Stoichiometry is the most likely recognition mode of RBGlc-3 toward Hg2+ ion, and the OFF–ON fluorescent mechanism of RBGlc-3 is proposed.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis of C-5a-substituted derivatives of 4-epi-isofagomine: notable
           β-galactosidase inhibitors and activity promotors of
           GM1-gangliosidosis related human lysosomal β-galactosidase mutant
           R201C
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Martin Thonhofer, Patrick Weber, Andres Gonzalez Santana, Christina Tysoe, Roland Fischer, Bettina M. Pabst, Eduard Paschke, Michael Schalli, Arnold E. Stütz, Marion Tschernutter, Werner Windischhofer, Stephen G. Withers
      From an easily available partially protected analog of 1-deoxy-L-gulo-nojirimycin, by chain-branching at C-4 and suitable modification, lipophilic analogs of the powerful β-D-galactosidase inhibitor 4-epi-isofagomine have been prepared. New compounds exhibit considerably improved inhibitory activities when compared with the unsubstituted parent compound and may serve as leads toward new pharmacological chaperones for GM1-gangliosidosis and Morquio B disease.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • The Staudinger/aza-Wittig/Grignard reaction as key step for the concise
           synthesis of 1-C-Alkyl-iminoalditol glycomimetics
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Manuel Zoidl, Andres Gonzalez Santana, Ana Torvisco, Christina Tysoe, Aloysius Siriwardena, Stephen G. Withers, Tanja M. Wrodnigg
      The scope of a one-pot tandem approach for the synthesis of C-1 alkyl iminoalditol derivatives with a Staudinger/aza-Wittig/Grignard cascade has been evaluated. The reaction conditions have been optimized for two azidodeoxy aldose substrates and a range of Grignard reagents. The nature of both, substrate as well as nucleophile, was found to control the stereoselectivity of the alkyl addition to the cyclic iminium intermediate at position C-1. This approach enabled the synthesis of a collection of C-alkyl iminoalditols, which were biologically evaluated as inhibitors against a set of standard glycoside hydrolases. All compounds were found to exhibit highly selective inhibition of β-glucosidase activity.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis of NAM-thiazoline derivatives as novel O-GlcNAcase inhibitors
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Hanchu Kong, Wei Chen, Tian Liu, Huizhe Lu, Qing Yang, Yanhong Dong, Xiaomei Liang, Shuhui Jin, Jianjun Zhang
      Human O-GlcNAcase (GH 84) and human β-N-acetyl-D-hexosaminidase (GH 20) from Homo sapiens are two therapeutic enzyme targets that share the same catalytic mechanism but play different physiological roles in vivo. Selective inhibition toward one of these enzymes is therefore of importance to regulate the corresponding bioprocess. Here ten new NAM-thiazoline derivatives were synthesized and subsequently characterized by NMR and HRMS. A preliminary bioassay showed that most of the synthesized compounds exhibited obvious selective inhibition against human O-GlcNAcase over human β-N-acetyl-D-hexosaminidase. Among the compounds tested, compound 7d (IC50 = 6.4 µM, hOGA; IC50>1 mM, hHex) and 7f (IC50 = 11.9 µM, hOGA; IC50>1 mM, hHex) proved to be a highly selective and potent inhibitor. Structure–activity relationship analysis indicated a correlation between the inhibitory activity and the size of the groups linked to the thiazoline ring.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis and DNA-binding properties of novel DNA cyclo-intercalators
           containing purine–glucuronic acid hybrids
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Renshuai Zhang, Shaopeng Chen, Xueting Wang, Rilei Yu, Mingjing Li, Sumei Ren, Tao Jiang
      Novel DNA cyclo-intercalators, which incorporated two intercalator subunits linked by two bridges, were synthesized. Binding of the compounds to calf-thymus DNA was studied by fluorescence spectroscopy, and docking simulations were used to predict the binding modes of these cyclic compounds. The spectral data demonstrated that all of these compounds can interact with CT-DNA. The sugar moiety played an important role in the process of binding between the intercalators containing glucuronic acid and DNA. The length and flexibility of the connecting bridges affected the binding affinity of the resultant cyclo-intercalators. Docking simulations showed that compounds 7 and 8 interact with DNA as mono-intercalators.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • A building block approach to the synthesis of a family of S-linked
           α-1,6-oligomannosides
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Tyson Belz, Spencer J. Williams
      The syntheses of α-1,6-S-linked methyl di-, tetra- and hexamannosides are reported. The sulfur linkages are generated through coupling of thiolates (derived from anomeric thioacetates or isothiouronium bromides) with 6-deoxy-6-iodo sugars. Two approaches are detailed that involve [2 + 2 + 2] construction from either the reducing end or the non-reducing end. In constructing from the reducing end, coupling of a disaccharide thioacetate with a 6'-iodo reducing end disaccharide, followed by activation of the resulting tetrasaccharide to a 6'''-iodide, and iterative coupling with the same disaccharide thioacetate afforded the S-linked hexasaccharide, as well as the intermediate di- and tetrasaccharides. On the other hand, construction from the non-reducing end involved coupling of the above disaccharide thioacetate with an anomeric S-trityl protected 6'-iodo disaccharide. The resulting S-trityl tetrasaccharide was converted to a tetrasaccharide thioacetate, which was coupled with the same anomeric S-trityl protected 6'-iodo disaccharide to afford the hexasaccharide, which was elaborated to the methyl thioglycoside. The developed methodology may prove useful for the construction of other S-linked oligosaccharides.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • CuAAC click chemistry with N-propargyl 1,5-dideoxy-1,5-imino-D-gulitol and
           N-propargyl 1,6-dideoxy-1,6-imino-D-mannitol provides access to
           triazole-linked piperidine and azepane pseudo-disaccharide iminosugars
           displaying glycosidase inhibitory properties
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Luís Otávio B. Zamoner, Valquíria Aragão-Leoneti, Susimaire P. Mantoani, Michael D. Rugen, Sergey A. Nepogodiev, Robert A. Field, Ivone Carvalho
      Protecting group-free synthesis of 1,2:5,6-di-anhydro-D-mannitol, followed by ring opening with propargylamine and subsequent ring closure produced a separable mix of piperidine N-propargyl 1,5-dideoxy-1,5-imino-D-gulitol and azepane N-propargyl 1,6-dideoxy-1,6-imino-D-mannitol. In O-acetylated form, these two building blocks were subjected to CuAAC click chemistry with a panel of three differently azide-substituted glucose building blocks, producing iminosugar pseudo-disaccharides in good yield. The overall panel of eight compounds, plus 1-deoxynojirimycin (DNJ) as a benchmark, was evaluated as prospective inhibitors of almond β-glucosidase, yeast α-glucosidase and barley β-amylase. The iminosugar pseudo-disaccharides showed no inhibitory activity against almond β-glucosidase, while the parent N-propargyl 1,5-dideoxy-1,5-imino-D-gulitol and N-propargyl 1,6-dideoxy-1,6-imino-D-mannitol likewise proved to be inactive against yeast α-glucosidase. Inhibitory activity could be reinstated in the former series by appropriate substitution on nitrogen. The greater activity of the piperidine could be rationalized based on docking studies. Further, potent inhibition of β-amylase was observed with compounds from both the piperidine and azepane series.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Multivalent ligand mimetics of LecA from P. aeruginosa: synthesis
           and NMR studies
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Davide Bini, Roberta Marchetti, Laura Russo, Antonio Molinaro, Alba Silipo, Laura Cipolla
      Molecular recognition of glycans plays an important role in glycomic and glycobiology studies. For example, pathogens have a number of different types of lectin for targeting host sugars. In bacteria, lectins exist sometimes as domains of bacterial toxins and exploit adhesion to glycoconjugates as a means of entering host cells. Herein, we describe the synthesis of three glycodendrons with the aim to dissect the fine structural details involved in the multivalent carbohydrate–protein interactions. LecA, from the pathogen Pseudomonas aeruginosa, has been used to characterize galactose dendrons interaction using one of the most widespread NMR technique for the elucidation of receptor-ligand binding in solution, the saturation transfer difference (STD) NMR. Furthermore, the effective hydrodynamic radius of each dendrimer recognized by LecA was estimated from the diffusion coefficients determined by pulsed-field-gradient stimulated echo (PFG-STE) NMR experiments.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Graphical contents list
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429




      PubDate: 2016-06-15T11:05:10Z
       
  • Carbohydrate CuAAC click chemistry for therapy and diagnosis
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429
      Author(s): Xiao-Peng He, Ya-Li Zeng, Yi Zang, Jia Li, Robert A. Field, Guo-Rong Chen
      Carbohydrates are important as signaling molecules and for cellular recognition events, therefore offering scope for the development of carbohydrate-mimetic diagnostics and drug candidates. As a consequence, the construction of carbohydrate-based bioactive compounds and sensors has become an active research area. While the advent of click chemistry has greatly accelerated the progress of medicinal chemistry and chemical biology, recent literature has seen an extensive use of such approaches to construct functionally diverse carbohydrate derivatives. Here we summarize some of the progress, covering the period 2010 to mid-2015, in CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition CuAAC “click chemistry” of carbohydrate derivatives, in the context of potential therapeutic and diagnostic tool development.
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      PubDate: 2016-06-15T11:05:10Z
       
  • Editorial board
    • Abstract: Publication date: 24 June 2016
      Source:Carbohydrate Research, Volume 429




      PubDate: 2016-06-15T11:05:10Z
       
  • Structure and gene cluster of the O-antigen of Escherichia coli O133
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Alexander S. Shashkov, Yuanyuan Zhang, Qiangzheng Sun, Xi Guo, Sof'ya N. Senchenkova, Andrei V. Perepelov, Yuriy A. Knirel
      The O-specific polysaccharide (O-antigen) of Escherichia coli O133 was obtained by mild acid hydrolysis of the lipopolysaccharide of E. coli O133. The structure of the hexasaccharide repeating unit of the polysaccharide was elucidated by 1H and 13C NMR spectroscopy, including a two-dimensional 1H–1H ROESY experiment: Functions of genes in the O-antigen gene cluster were putatively identified by comparison with sequences in the available databases and, particularly, an encoded predicted multifunctional glycosyltransferase was assigned to three α-l-rhamnosidic linkages.
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      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis of 6-Phosphofructose Aspartic Acid and Some Related Amadori
           Compounds
    • Abstract: Publication date: Available online 14 May 2016
      Source:Carbohydrate Research
      Author(s): Alexandar L. Hansen, Edward J. Behrman
      We describe the synthesis and characterization of 6-phosphofructose-aspartic acid, an intermediate in the metabolism of fructose-asparagine by Salmonella. We also report improved syntheses of fructose-asparagine itself and of fructose-aspartic acid.
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       
  • Structure and gene cluster of the O-antigen of Escherichia coli O156
           containing a pyruvic acid acetal
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Zhifeng Duan, Sof'ya N. Senchenkova, Xi Guo, Andrei V. Perepelov, Alexander S. Shashkov, Bin Liu, Yuriy A. Knirel
      The lipopolysaccharide of Escherichia coli O156 was degraded under mild acidic and alkaline conditions and the resulting polysaccharides were studied by sugar analysis and 1H and 13C NMR spectroscopy. The following structure of the pentasaccharide repeating unit of the O-polysaccharide was established: where Rpyr indicates R-configurated pyruvic acid acetal. Minor O-acetyl groups also were present and tentatively localized on the Gal residues. The gene cluster for biosynthesis of the O-antigen of E. coli O156 was analyzed and shown to be consistent with the O-polysaccharide structure.
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       
  • Synthesis of the 2-deoxy trisaccharide glycal of antitumor antibiotics
           landomycins A and E
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Xiaohua Li, Justin Woodward, Ali Hourani, Danyang Zhu, Sabrine Ayoub, Jianglong Zhu
      Synthesis of the 2-deoxy trisaccharide glycal of antitumor antibiotics landomycins A and E has been described. The synthesis involves an anomeric O-alkylation for the synthesis of 2-deoxy β-linked disaccharide, a tert-butyldimethylsilyl triflate-catalyzed α-selective L-rhodinosylation, and a lithium 4,4′-di-tert-butylbiphenyl-mediated reductive debenzylation and concomitant reductive lithiation-elimination for the production of the 2-deoxy trisaccharide glycal.
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       
  • Biochemical characterization of the novel α-1,
           3-galactosyltransferase WclR from Escherichia coli O3
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Chao Chen, Bin Liu, Yongchang Xu, Natalia Utkina, Dawei Zhou, Leonid Danilov, Vladimir Torgov, Vladimir Veselovsky, Lu Feng
      Glycosyltransferases (GTs) catalyze the formation of regio- and stereo-specific glycosidic linkages between specific sugar donors and recipients. In this study, the function of the gene wclR from the Escherichia coli O3 O-antigen gene cluster that encodes an α 1, 3-galactosyltransferase (GalT) that acts on the linkage Gal α 1, 3-GlcNAc was biochemically characterized. WclR was expressed in E. coli BL21 (DE3), and the enzymatic product was identified by liquid chromatography-mass spectrometry (LC-MS), collision-induced dissociation electrospray ionization ion trap multiple tandem MS (CID-ESI-IT-MSn) and galactosidase digestion, using UDP-Gal as the donor substrate and the synthetic acceptor substrate GlcNAc-PP-De (decyl diphosphate N-acetylglucosamine). The physiochemical properties and the substrate specificity of WclR were investigated. WclR is the first bacterial GalT characterized that acts on the linkage Gal α 1, 3-GlcNAc. This study enhanced our knowledge of the diversified functions of GTs and provided a novel enzyme source for possible pharmaceutical application.
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       

  •        1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose
           (PGG) analogs: design, synthesis, anti-tumor and anti-oxidant activities
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Qurat-ul-ain Shaikh, Meiting Yang, Khadim Hussain Memon, Mehreen Lateef, Du Na, Shengbiao Wan, Deslandes Eric, Lijuan Zhang, Tao Jiang
      1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) 12 has been reported for its antioxidant activities, where the free OH groups in PGG seem to be critical for activities. To explore PGG-based compounds as chemotherapeutic agents and to analyze the contribution of specific OH groups in PGG for anti-cancer activities, we designed and synthesized a series of 27 benzoic and cinnamic acid analogs of PGG. These analogs were tested for cytotoxicities against two human lung (A549 and H1299) and two human colon (HCT116 and HT29) cancer cell lines. Compound 12 (PGG) had highest cytotoxicities against HCT116 and A549 cells with IC50 of 1.61 µM and 3.02 µM, respectively. In contrast, the compound 16 (1,2,3,4,6-pentakis[-O-(4-hydroxy-3-methoxybenzoyl)]-α,β-D-glucopyranose, PVG) was most effective at killing HT29 and H1299 cells with IC50 of 1.76 µM and 3.65 µM, respectively, indicating the mutual contribution of m-methoxy and p-hydroxy groups to the observed cytotoxicities. Moreover, cinnamic acid analogs were less active than the benzoic acid analogs evidenced by higher IC50 values. Furthermore, in cinnamic acid analogs the hydrogenation of double bond to saturated 2-C side chain enhance the cytotoxicities in all four cell lines. Compounds also possess good anti-oxidant and reducing activities. Compound 12 and 26 show the highest antioxidant and reducing activities.
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       
  • Efficient chemoenzymatic synthesis of 4-nitrophenyl
           β-d-apiofuranoside and its use in screening of
           β-d-apiofuranosidases
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Peter Kis, Elena Potocká, Vladimír Mastihuba, Mária Mastihubová
      4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enzymatic step—benzoylation of primary hydroxyl of 2,3-isopropylidene-α,β-d-apiofuranose catalysed by Lipolase 100T and stereoselective β-d-apiofuranosylation of p-nitrophenol using BF3⋅OEt2/Et3N. The product was used for screening of β-d-apiofuranosidase activity in 61 samples of crude commercial enzymes and plant materials. Fifteen enzyme preparations originating from different strains of genera Aspergillus display β-d-apiofuranosidase activity. The highest activity was found in Rapidase AR 2000 (78.27 U/g) and lyophilized Viscozyme L (64,36 U/g).
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       
  • Structural determination of the polysaccharide isolated from biofilms
           produced by a clinical strain of klebsiella pneumoniae
    • Abstract: Publication date: Available online 5 May 2016
      Source:Carbohydrate Research
      Author(s): Paola Cescutti, Gianluigi De Benedetto, Roberto Rizzo
      Klebsiella pneumoniae are Gram negative opportunistic pathogens producing capsular (K) polysaccharides. Seventy seven different K antigens have been described and they are the basis for K serotyping. Capsular polysaccharides are important virulence factors and have a relevant role for the structure of biofilm communities. Nevertheless, little information is available on the polysaccharides produced in biofilm matrices by Klebsiella spp. In the present study, a clinical isolate of Klebsiella pneumoniae was grown both on cellulose membranes deposited on agar plates, where it formed an adherent biofilm, and in liquid medium, where it formed floating biofilms (flocs). Extraction and purification of the polysaccharide fraction showed that only one main carbohydrate polymer was present in both adherent biofilms and flocs. Composition and linkage analysis, Smith degradation followed by ESI-MS, 1D and 2D NMR spectroscopy revealed that the polysaccharide belong to the type K24 and has the following structure:
      Graphical abstract image

      PubDate: 2016-05-07T07:00:11Z
       
  • Binding activities of non-β-glucan glycoclusters to dectin-1 and
           exploration of their binding site
    • Abstract: Publication date: Available online 6 May 2016
      Source:Carbohydrate Research
      Author(s): Shan Jiang, Shan Niu, Wang Yao, Zhong-Jun Li, Qing Li
      Dectin-1, which specifically recognizes β-(1,3)-glucans, plays an important role in innate immune responses. For the first time, in this study we found that a series of non-β-glucan glycoclusters can bind to dectin-1 by means of surface plasmon resonance (SPR) assay. Hexavalent lactosides Ju-6 showed strongest affinity property (K D=1.6 µM). Interestingly, a continuous binding-dissociation experiment on SPR showed that Ju-6 and Laminarin binding to dectin-1 are independent of each other. Moreover, RT-PCR assay showed that Ju-6 cannot up-regulate cytokine gene expression, or inhibit the promoting effect caused by Zymosan (a long-chain β-glucan). These results indicated that there might be a possible new carbohydrate binding site on dectin-1.
      Graphical abstract image

      PubDate: 2016-05-07T07:00:11Z
       
  • Facile synthesis of aminooxy glycosides by gold(III)-catalyzed
           glycosidation
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Shivaji A. Thadke, Mahesh Neralkar, Srinivas Hotha
      The O-glycosidation of hydroxysuccinimides and hydroxyphthalimides with a variety of aldose derived propargyl 1,2-orthoesters under the gold(III)-catalyzed glycosidation conditions is reported. A wide range of hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized from corresponding glycosyl orthoesters including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.
      Graphical abstract image

      PubDate: 2016-05-07T07:00:11Z
       
  • Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-,
           and 1,6-mannan oligomers
    • Abstract: Publication date: 22 July 2016
      Source:Carbohydrate Research, Volume 430
      Author(s): Shu-Lun Tang, Nicola L.B. Pohl
      Automated solution-phase syntheses of β-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a β-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short β-mannan oligomers with limited loading of glycosyl donor—as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including use of a C-5 ester as a protecting group that could be converted under reductive conditions to a hydroxymethyl group for chain extension.
      Graphical abstract image

      PubDate: 2016-05-07T07:00:11Z
       
  • Block synthesis of A (type 2) and B (type 2) tetrasaccharides related to
           the human ABO blood group system
    • Abstract: Publication date: Available online 4 May 2016
      Source:Carbohydrate Research
      Author(s): Ivan M. Ryzhov, Elena Yu. Korchagina, Inna S. Popova, Tatiana V. Tyrtysh, Alexander S. Paramonov, Nicolai V. Bovin
      Herein we report the synthesis of 3-aminopropyl glycosides of A (type 2) and B (type 2) tetrasaccharides via [3+1] block scheme. Peracetylated trichloroacetimidates of A and B trisaccharides were used as glycosyl donors. The well-known low reactivity of 4-OH group of N-acetyl-d-glucosamine forced us to test four glucosamine derivatives (3-Bz-1,6-anhydro-GlcNAc, and 3-trifluoroacetamidopropyl β-glycosydes of 3-Ac-6-Bn-GlcNAc, 3-Ac-6-Bn-GlcN3, and 3-Ac-6-Bn-GlcNAc2) to select the best glycosyl acceptor for the synthesis of type 2 tetrasaccharides. The desired tetrasacchrides were not isolated, when 3-trifluoroacetamidopropyl glycosyde of 3-Ac-6-Bn-GlcNAcβ was glycosylated. Glycosylation of 3-Bz-1,6-anhydro-GlcNAc derivative resulted in α-glycoside as a major product. High stereospecificity was achieved only in the synthesis of B (type 2) tetrasaccharide, when 3-trifluoroacetamidopropyl 3-Ac-6-Bn-GlcNAc2β was applied as the glycosyl acceptor (β/α 5:1), whereas glycosylation with trichloroacetimidate of A trisaccharide was not stereospecific (β/α 1.3:1). Glycosylation of 3-trifluoroacetamidopropyl glycosyde of 3-Ac-6-Bn-GlcN3β with trichloroacetimidates of A and B trisaccharides provided the same stereochemical yield (β/α 1.5:1).
      Graphical abstract image

      PubDate: 2016-05-05T06:55:12Z
       
  • Structural characterization of the lipoteichoic acid isolated from
           staphylococcus sciuri w620
    • Abstract: Publication date: Available online 4 May 2016
      Source:Carbohydrate Research
      Author(s): Katarzyna A. Duda, Sandra Petersen, Otto Holst
      Lipoteichoic acid (LTA) is an important cell envelope compound of Gram-positive bacteria. LTA isolated from allergy-protective Staphylococcus sciuri W620 strain was characterized by chemical analyses as well as 1D and 2D NMR experiments. Compositional analyses indicated the presence of glycerol (Gro), phosphate-Gro, alanine-Gro, glucose (Glc) and fatty acids. The studied strain produced LTA with backbone composed of glycerol-phosphate repeating units only substituted with d-alanine (Ala) and the lipid anchor, typically for genus Staphyloccocus, possessing the structure β-d-Glcp(1→6)- β-d-Glcp(1→3)-1,2-diacyl-sn-Gro.
      Graphical abstract image

      PubDate: 2016-05-05T06:55:12Z
       
  • Preparation of chitooligosaccharides from fungal waste mycelium by
           recombinant chitinase
    • Abstract: Publication date: Available online 19 April 2016
      Source:Carbohydrate Research
      Author(s): Mengyuan Lv, Ying Hu, Michael G. Gänzle, Jianguo Lin, Changgao Wang, Jun Cai
      This study aimed to develop an enzymatic method for conversion of chitin from fungal waste mycelia to chitooligosaccharides. The recombinant chitinase LlChi18A from Lactococcus lactis was over-expressed by Escherichia coli BL21 (DE3) and purified by affinity chromatography. The enzymatic properties of the purified enzyme were studied by chitin oligosaccharides. Waste mycelium was pre-treated by alkaline. The optimal conditions for hydrolysis of fungal chitin by recombinant chitinase were determined by Shales method. HPLC/ESI-MS was used to determine the content of N-acetylglucosamine and chitooligosaccharides after hydrolysis. The level of reducing sugar released from pretreated mycelium by chitinase increased with the reaction time during 6 days. The main product in the hydrolysates was N,N'-diacetylchitobiose. After hydrolysis by chitinase for 5 d, the yield of N,N'-diacetylchitobiose from waste mycelium was around 10% with estimated purity around 70%. Combination of chitinase and snailase remarkably increased the yield to 24% with purity of 78%. Fungal mycelium which contains chitin is a new potential source for obtaining food grade chitooligosaccharides.
      Graphical abstract image

      PubDate: 2016-04-22T11:49:55Z
       
 
 
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