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  Subjects -> CHEMISTRY (Total: 860 journals)
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    - CHEMISTRY (603 journals)
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CHEMISTRY (603 journals)                  1 2 3 4 | Last

Showing 1 - 200 of 735 Journals sorted alphabetically
2D Materials     Hybrid Journal   (Followers: 13)
Accreditation and Quality Assurance: Journal for Quality, Comparability and Reliability in Chemical Measurement     Hybrid Journal   (Followers: 26)
ACS Catalysis     Full-text available via subscription   (Followers: 40)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 20)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 23)
ACS Macro Letters     Full-text available via subscription   (Followers: 25)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 41)
ACS Nano     Full-text available via subscription   (Followers: 260)
ACS Photonics     Full-text available via subscription   (Followers: 12)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 23)
Acta Chemica Iasi     Open Access   (Followers: 2)
Acta Chimica Sinica     Full-text available via subscription   (Followers: 1)
Acta Chimica Slovaca     Open Access   (Followers: 1)
Acta Chimica Slovenica     Open Access  
Acta Chromatographica     Full-text available via subscription   (Followers: 9)
Acta Facultatis Medicae Naissensis     Open Access  
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 5)
Acta Scientifica Naturalis     Open Access   (Followers: 2)
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 5)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 8)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 5)
Advanced Functional Materials     Hybrid Journal   (Followers: 51)
Advanced Science Focus     Free   (Followers: 3)
Advances in Chemical Engineering and Science     Open Access   (Followers: 59)
Advances in Chemical Science     Open Access   (Followers: 14)
Advances in Chemistry     Open Access   (Followers: 16)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 18)
Advances in Drug Research     Full-text available via subscription   (Followers: 23)
Advances in Enzyme Research     Open Access   (Followers: 9)
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Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 9)
Advances in Materials Physics and Chemistry     Open Access   (Followers: 24)
Advances in Nanoparticles     Open Access   (Followers: 14)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 16)
Advances in Polymer Science     Hybrid Journal   (Followers: 41)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 18)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 20)
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: 2)
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: 3)
AMB Express     Open Access   (Followers: 1)
Ambix     Hybrid Journal   (Followers: 3)
American Journal of Biochemistry and Biotechnology     Open Access   (Followers: 67)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 15)
American Journal of Chemistry     Open Access   (Followers: 28)
American Journal of Plant Physiology     Open Access   (Followers: 14)
American Mineralogist     Hybrid Journal   (Followers: 15)
Analyst     Full-text available via subscription   (Followers: 39)
Angewandte Chemie     Hybrid Journal   (Followers: 167)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 237)
Annales UMCS, Chemia     Open Access   (Followers: 1)
Annals of Clinical Chemistry and Laboratory Medicine     Open Access   (Followers: 4)
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)
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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: 16)
Anti-Infective Agents     Hybrid Journal   (Followers: 3)
Antiviral Chemistry and Chemotherapy     Hybrid Journal   (Followers: 1)
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 7)
Applied Spectroscopy     Full-text available via subscription   (Followers: 22)
Applied Surface Science     Hybrid Journal   (Followers: 28)
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: 4)
Australian Journal of Chemistry     Hybrid Journal   (Followers: 7)
Autophagy     Hybrid Journal   (Followers: 2)
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 10)
Biochemistry     Full-text available via subscription   (Followers: 339)
Biochemistry Insights     Open Access   (Followers: 6)
Biochemistry Research International     Open Access   (Followers: 6)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 9)
Bioinspired Materials     Open Access   (Followers: 5)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 2)
Biointerphases     Open Access   (Followers: 1)
Biology, Medicine, & Natural Product Chemistry     Open Access   (Followers: 1)
Biomacromolecules     Full-text available via subscription   (Followers: 19)
Biomass Conversion and Biorefinery     Partially Free   (Followers: 10)
Biomedical Chromatography     Hybrid Journal   (Followers: 6)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 3)
BioNanoScience     Partially Free   (Followers: 5)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 121)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 85)
Bioorganic Chemistry     Hybrid Journal   (Followers: 10)
Biopolymers     Hybrid Journal   (Followers: 18)
Biosensors     Open Access   (Followers: 2)
Biotechnic and Histochemistry     Hybrid Journal   (Followers: 1)
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: 69)
Catalysis for Sustainable Energy     Open Access   (Followers: 7)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 8)
Catalysis Science and Technology     Free   (Followers: 8)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 3)
Catalysts     Open Access   (Followers: 9)
Cellulose     Hybrid Journal   (Followers: 7)
Cereal Chemistry     Full-text available via subscription   (Followers: 5)
ChemBioEng Reviews     Full-text available via subscription   (Followers: 1)
ChemCatChem     Hybrid Journal   (Followers: 8)
Chemical and Engineering News     Free   (Followers: 16)
Chemical Bulletin of Kazakh National University     Open Access  
Chemical Communications     Full-text available via subscription   (Followers: 71)
Chemical Engineering Research and Design     Hybrid Journal   (Followers: 25)
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: 23)
Chemical Technology     Open Access   (Followers: 16)
Chemical Vapor Deposition     Hybrid Journal   (Followers: 5)
Chemical Week     Full-text available via subscription   (Followers: 8)
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: 31)
Chemistry & Industry     Hybrid Journal   (Followers: 5)
Chemistry - A European Journal     Hybrid Journal   (Followers: 153)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 16)
Chemistry and Materials Research     Open Access   (Followers: 20)
Chemistry Central Journal     Open Access   (Followers: 4)
Chemistry Education Research and Practice     Free   (Followers: 5)
Chemistry in Education     Open Access   (Followers: 9)
Chemistry International     Hybrid Journal   (Followers: 2)
Chemistry Letters     Full-text available via subscription   (Followers: 43)
Chemistry of Materials     Full-text available via subscription   (Followers: 244)
Chemistry of Natural Compounds     Hybrid Journal   (Followers: 9)
Chemistry World     Full-text available via subscription   (Followers: 22)
Chemistry-Didactics-Ecology-Metrology     Open Access   (Followers: 1)
ChemistryOpen     Open Access   (Followers: 2)
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: 10)
Chromatographia     Hybrid Journal   (Followers: 24)
Chromatography     Open Access   (Followers: 2)
Clay Minerals     Full-text available via subscription   (Followers: 10)
Cogent Chemistry     Open Access  
Colloid and Interface Science Communications     Open Access  
Colloid and Polymer Science     Hybrid Journal   (Followers: 10)
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)
Composite Interfaces     Hybrid Journal   (Followers: 6)
Comprehensive Chemical Kinetics     Full-text available via subscription   (Followers: 2)
Comptes Rendus Chimie     Full-text available via subscription  
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Computational Biology and Chemistry     Hybrid Journal   (Followers: 11)
Computational Chemistry     Open Access   (Followers: 2)
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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)
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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)
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Current Science     Open Access   (Followers: 64)
Dalton Transactions     Full-text available via subscription   (Followers: 23)
Detection     Open Access   (Followers: 2)
Developments in Geochemistry     Full-text available via subscription   (Followers: 2)
Diamond and Related Materials     Hybrid Journal   (Followers: 12)
Dislocations in Solids     Full-text available via subscription  
Doklady Chemistry     Hybrid Journal  
Drying Technology: An International Journal     Hybrid Journal   (Followers: 4)
Eclética Química     Open Access   (Followers: 1)
Ecological Chemistry and Engineering S     Open Access   (Followers: 3)

        1 2 3 4 | Last

Journal Cover Carbohydrate Research
  [SJR: 0.612]   [H-I: 98]   [26 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
   Published by Elsevier Homepage  [3120 journals]
  • Synthesis of sulfamide analogues of deoxthymidine monophosphate as
           potential inhibitors of mycobacterial cell wall biosynthesis
    • Abstract: Publication date: 2 March 2018
      Source:Carbohydrate Research, Volume 457
      Author(s): Kajitha Suthagar, Wanting Jiao, Hélène Munier-Lehmann, Antony J. Fairbanks
      The recently discovered enzyme Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt), which catalyses the phosphorylation of deoxythymidine monophosphate (dTMP) to give deoxythymidine diphosphate (dTDP), is indispensable for the growth and survival of M. tuberculosis as it plays an essential role in DNA synthesis. Inhibition of TMPKmt is an attractive avenue for the development of novel anti-tuberculosis agents. Based on the premise that sulfamide may be a suitable isostere of phosphate, deoxythymidine analogues comprising various substituted sulfamides at C5′ were modelled in silico into the active site of TMPKmt (PDB accession code: 1N5K) using induced-fit docking methods. A selection of modelled compounds was synthesized, and their activity as inhibitors of TMPKmt was evaluated. Three compounds showed competitive inhibition of TMPKmt in the micromolar range (10–50 μM). Compounds were tested in vitro for anti-mycobacterial activity against M. smegmatis: three compounds showed weak anti-mycobacterial activity (MIC 250 μg/mL).
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • L-Proline/CeCl3·7H2O-NaI mediated stereoselective synthesis of α-2-deoxy
           glycosides from glucal
    • Abstract: Publication date: 2 March 2018
      Source:Carbohydrate Research, Volume 457
      Author(s): Mukul R. Gupta, Kratima Thakur, Naveen K. Khare
      Glucal with different alcohols can be converted into the corresponding 2-deoxy glycosides without Ferrier rearrangement in high yield by treatment with eco friendly transition metal based catalysts [CuCl3·2H2O-NaI (A) or CeCl3·7H2O-NaI (B)] and chiral amine ligand L-proline at various reaction conditions which were optimized for stereoselectivity. The catalyst CeCl3·7H2O-NaI (B) and ligand L-proline in toluene, was found to be much more efficient and high atom economic for the stereoselective glycosidation of propargyl alcohol with glucal, afforded exclusively α-2-deoxy propargyl glycoside in 98% optimized yield. The ligand L-proline was used for the first time in stereoselective glycosidation of α-2-deoxy glycosides involving glucal and alcohols.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • Structure elucidation of the O-specific polysaccharide by NMR spectroscopy
           and selective cleavage and genetic characterization of the O-antigen of
           Escherichia albertii O5
    • Abstract: Publication date: 2 March 2018
      Source:Carbohydrate Research, Volume 457
      Author(s): Olesya I. Naumenko, Han Zheng, Jianping Wang, Sof'ya N. Senchenkova, Hong Wang, Alexander S. Shashkov, Alexander O. Chizhov, Qun Li, Yuriy A. Knirel, Yanwen Xiong
      The O-specific polysaccharide (O-antigen) was obtained by mild acid degradation of the lipopolysaccharide of Escherichia albertii O5 (strain T150248) and studied by sugar analysis, selective cleavages of glycosidic linkages, and 1D and 2D 1H and 13C NMR spectroscopy. Partial solvolysis with anh (anhydrous) CF3CO2H and hydrolysis with 0.05 M CF3CO2H cleaved predominantly the glycosidic linkage of β-GalpNAc or β-Galf, respectively, whereas the linkages of α-GlcpNAc and β-Galp were stable. Mixtures of the corresponding tri- and tetra-saccharides thus obtained were studied by NMR spectroscopy and high-resolution ESI MS. The following new structure was established for the tetrasaccharide repeat (O-unit) of the O-polysaccharide: →4)-α-d-GlcpNAc-(1 → 4)-β-d-Galp6Ac-(1 → 6)-β-d-Galf-(1 → 3)-β-d-GalpNAc-(1→where the degree of O-acetylation of d-Galp is ∼70%. The O-polysaccharide studied has a β-d-Galp-(1 → 6)-β-d-Galf-(1 → 3)-β-d-GalpNAc trisaccharide fragment in common with the O-polysaccharides of E. albertii O7, Escherichia coli O124 and O164, and Shigella dysenteriae type 3 studied earlier. The orf5-7 in the O-antigen gene cluster of E. albertii O5 are 47%, 78%, and 75% identical on the amino acid level to genes for predicted enzymes of E. albertii O7, including Galp-transferase wfeS, UDP-d-Galp mutase glf, and Galf-transferase wfeT, respectively, which are putatively involved with the synthesis of the shared trisaccharide fragment of the O-polysaccharides. The occurrence upstream of the O-antigen gene cluster of a 4-epimerase gene gnu for conversion of undecaprenyl diphosphate-linked d-GlcNAc (UndPP-d-GlcNAc) into UndPP-d-GalNAc indicates that d-GalNAc is the first monosaccharide of the O-unit, and hence the O-units are interlinked in the O-polysaccharide of E. albertii O5 by the β-d-GalpNAc-(1 → 4)-α-d-GlcpNAc linkage.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • Proper balance of solvent-solute and solute-solute interactions in the
           treatment of the diffusion of glucose using the Drude polarizable force
           field
    • Abstract: Publication date: 2 March 2018
      Source:Carbohydrate Research, Volume 457
      Author(s): Mingjun Yang, Asaminew H. Aytenfisu, Alexander D. MacKerell
      Motivated by underestimation of the diffusion constant of glucose in aqueous solution at high glucose concentrations we performed additional optimization of the Drude polarizable hexopyranose monosaccharide force field. This indicated aggregation of the glucose at higher concentrations, which is a concern for studies of complex glycan systems such as the HIV Envelope where high effective concentrations of sugars are present. High-level quantum mechanical calculations were undertaken on water monohydrate-glucose interactions, on water cluster-glucose interactions and on glucose-glucose dimers in stacked (parallel) and perpendicular orientations. Optimization of the nonbond and dihedral parameters targeting these data yielded a revised model that showed improved agreement with experimental aqueous diffusion data. However, limitations in the diffusion constants were still present. These were due to the SWM4-NDP inherently overestimating the diffusion constant of water, a problem that was validated by calculation of the aqueous diffusion constants using the SWM6-NDP water model. In addition, results show the water diffusion constant to be significantly overestimated at high glucose concentrations though the glucose diffusion is in satisfactory agreement with experiment. These results indicate the subtle balance of water-sugar, water-water and sugar-sugar interactions that needs to be properly modeled to account for the full range of aqueous behavior of sugars in aqueous solution.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • Scope and limitations of carbohydrate hydrolysis for de novo glycan
           sequencing using a hydrogen peroxide/metallopeptide-based glycosidase
           mimetic
    • Abstract: Publication date: Available online 3 February 2018
      Source:Carbohydrate Research
      Author(s): Tianyuan Peng, Zachary Wooke, Nicola L.B. Pohl
      Acidic hydrolysis is commonly used as a first step to break down oligo- and polysaccharides into monosaccharide units for structural analysis. While easy to set up and amenable to mass spectrometry detection, acid hydrolysis is not without its drawbacks. For example, ring-destruction side reactions and degradation products, along with difficulties in optimizing conditions from analyte to analyte, greatly limits its broad utility. Herein we report studies on a hydrogen peroxide/CuGGH metallopeptide-based glycosidase mimetic design for a more efficient and controllable carbohydrate hydrolysis. A library of methyl glycosides consisting of ten common monosaccharide substrates, along with oligosaccharide substrates, was screened with the artificial glycosidase for hydrolytic activity in a high-throughput format with a robotic liquid handling system. The artificial glycosidase was found to be active towards most screened linkages, including alpha- and beta-anomers, thus serving as a potential alternative method for traditional acidic hydrolysis approaches of oligosaccharides.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • Preparation and structural characterization of regioselective
           4-O/6-O-desulfated chondroitin sulfate
    • Abstract: Publication date: Available online 2 February 2018
      Source:Carbohydrate Research
      Author(s): Wenwei Han, Quancai Li, Youjing Lv, QingChi Wang, Xia Zhao
      The sulfation pattern plays a crucial role in chondroitin sulfate (CS) biological activity, and preparation of CS with defined structure is essential for accurate pharmacological study. In this study, we focused on the preparation of regioselective 4-O/6-O-desulfated CS derived from porcine, employing a dimethyl sulfoxide-methanol (DMSO-MeOH) method and an N-methyl-N-(trimethylsilyl) -trifluoroacetamide (MTSTFA) method CS, respectively. Results showed that the sulfate at C4 position (4-O-S) of N-acetylgalactosamine (GalNAc) was selectively removed by the DMSO-MeOH method, and the sulfate at C6 position (6-O-S) of GalNAc was selectively removed by the MTSTFA method. Structures of desulfated CS were characterized by means of FT-IR, NMR and disaccharide composition analysis. The preparations of regioselective 4-O/6-O-desulfated CS are powerful for the study of structure-activity relationship of CS.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • New insight in crosslinking degree determination for crosslinked starch
    • Abstract: Publication date: Available online 1 February 2018
      Source:Carbohydrate Research
      Author(s): Tingting Kou, Qunyu Gao
      The crosslinked starch has been studied for many years, but it is difficult to characterize degree of substitution on crosslinking of the very high and low crosslinked starches. The available approaches (including viscosity, settling volume, and P content) all have their limitations, i.e., not applicable in a large scope, pollution problem, and can not reflect the internal structure change. Here in this paper starch-iodine (St-I) method was proposed as a new approach to characterize the crosslinking degree. In this investigation, three starches of A, B, and C crystalline pattern with different amount (from very low to very high, 0.01, 0.05, 0.1, 0.5, 1, 5, 10%) of crosslinking reagent added were studied. This method is based on the mechanism that crosslinking reaction take place between amylose/amylopectin, amylopectin/amylopectin, whereas the amylose dose not crosslink one another. After crosslinked to amylopectin, the result amylose-amylopectin complex can be considered as a new amylopectin. Results showed that the St-I method can characterize all the crosslinked starches of the three starches, at low reagent level (0.01–0.1%), the amylose was found to decrease rapidly, this can also replace the viscosity method, whereas at high reagent level (1–10%), although the significant differences can still be observed, the effect was not so obvious as it for the lower crosslinked starches, here we firstly applied dose efficiency to characterize this phenomenon, which was informative and helpful in determining this modification process.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • Synthesis and conformational analysis of
           D-gluco-pyranosyl-(6,6′)-D-gluco-pyranuronate, a model compound for the
           inter-glycan 6,6′-ester linkage
    • Abstract: Publication date: Available online 31 January 2018
      Source:Carbohydrate Research
      Author(s): Sven Hackbusch, Amelia Watson, Andreas H. Franz
      The synthesis of a 6,6′-ester linked disaccharide analog model compound was achieved in five steps from d-glucose and featured a key oxidative esterification transformation. The synthesized d- gluco-pyranosyl-(6,6′)-d- gluco-pyranuronate was characterized in D2O using NMR spectroscopy. Using the experimental data together with molecular dynamics simulations (TIP3P, water), a model of the compound's conformational behavior was established. The effect of the 6,6′-ester linkage on the solution phase structure was compared to that of the previously reported 6,6′-ether linkage in a disaccharide analog. Based on the established models, the ester linkage was found to have a profound effect on the overall shape of the molecule.
      Graphical abstract image

      PubDate: 2018-02-04T18:03:15Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455


      PubDate: 2018-02-04T18:03:15Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455


      PubDate: 2018-02-04T18:03:15Z
       
  • A concise route to access C-glycosidic tetrazolyl analogues of Kdo as
           bioisosteres
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Bettina Riedl, Walther Schmid
      Ulosonic acids are an important class of carbohydrates, including well-known representatives as 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-d-glycero-d-galacto-non-2-ulosonic acid (Kdn) and N-Acetylneuraminic acid (Neu5Ac). As part of the lipopolysaccharides (LPS) and capsular polysaccharides (CPS, K-antigen), these carbohydrates can be found on the surfaces of, both, Gram-positive and Gram-negative bacteria. We developed a synthetic approach to access tetrazole-derivatives of these compounds. Tetrazoles have shown to be ideal analogues for the bioisosteric replacement of carboxylic acids in several drugs, improving biological activity and pharmacokinetic properties. The presented route features indium-mediated allylation with subsequent [2 + 3]-cycloaddition as key steps, leading to tetrazole-derivative of Kdo and its corresponding C-4 epimer. The route is flexible enough to be adapted to the preparation of further tetrazole ulosonic acids.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Bisecting GlcNAc restricts conformations of branches in model N-glycans
           with GlcNAc termini
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Shinya Hanashima, Akitsugu Suga, Yoshiki Yamaguchi
      Bisected N-glycans play significant roles in tumor migration and Alzheimer's disease through modulating the action and localization of their carrier proteins. Such biological functions are often discussed in terms of the conformation of the attached N-glycans with or without bisecting GlcNAc. To obtain insights into the effects of bisecting GlcNAc on glycan conformation, a systematic NMR structural analysis was performed on two pairs of synthetic N-glycans, with and without bisecting GlcNAc. The analysis reveals that terminal GlcNAcs and bisecting GlcNAc cooperate to restrict the conformations of both the α1-3 and α1-6 branches of N-glycans. 1H and 13C chemical shift comparisons suggest that bisecting GlcNAc directly modulates local conformation. Unique NOE correlations between core-mannose and the α1-3 branch mannose as well as the 3 J C-H constant of the glycoside linkage indicate that bisecting GlcNAc restricts the conformation of the 1–3 branch. The angles of the glycosidic bonds between core-mannose and α1-6 branch mannose derived from 3 J C-H and 3 J H-H coupling constants show that terminal GlcNAcs restrict the distribution of the ψ angle to 180° and the bisecting GlcNAc increases the distribution of the ω angle +60° in the presence of terminal GlcNAcs. It is feasible that restriction of branch conformations by bisecting GlcNAc has important consequences for protein-glycan interplay and following biological events.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Reaction specificity of keratanase II in the transglycosylation using the
           sugar oxazolines having keratan sulfate repeating units
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Yuji Yamazaki, Shunsaku Kimura, Masashi Ohmae
      The reaction specificity of the transglycosylation catalyzed by keratanase II from Bacillus circulans KsT202 (KSase II) was studied by using the oxazoline derivatives having keratan sulfate repeating units. The addition of 10% organic cosolvent reduced the activity for the enzymatic transglycosylation. The oxazoline derivative of 6-O-sulfonato-N-acetyllactosamine (su-LacNAc) was processively oligomerized to the corresponding hexamer or longer by the enzyme. This result strongly implies that the enzyme has the large positively numbered subsites. In contrast, the transglycosylation of the su-LacNAc oxazoline donor with the 6-O-sulfonato-Lewis X (su-LeX) acceptor solely gave the su-LacNAc-su-LeX pentasaccharide. In addition, both the oxazoline derivatives of su-LeX and 6,6′-di-O-sulfonato-LacNAc have been exclusively oligomerized to the corresponding dimers respectively. These results strongly suggest that the steric hindrance exists around the (+3)(+4) subsites in KSase II. Furthermore, KSase II-catalyzed reaction of the excess su-LeX oxazoline with the su-LacNAc gave the su-LeX-su-LacNAc pentasaccharide as the sole transglycosylation product, also implying the steric hindrance at the catalytic center hampering processive shift of this pentasaccharide. Thus, KSase II has the sterically crowded structures at the catalytic center and around the (+3)(+4) subsites, which are all expected to be tunnel-like.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Conjugation of carbohydrates to proteins using di(triethylene glycol
           monomethyl ether) squaric acid ester revisited
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Peng Xu, Michael N. Trinh, Pavol Kováč
      Properties of di(triethylene glycol monomethyl ether) squarate relevant to conjugation of carbohydrates to proteins have been reinvestigated and compared with those of dimethyl squarate. It is concluded that the commercially available, crystalline dimethyl squarate remains the most convenient and efficient reagent for conjugation of amine-containing carbohydrates to proteins by a two-step or one-pot conjugation protocol.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Synthesis of tetracyclic azasugars fused benzo[e][1,3]thiazin-4-one by the
           tandem Staudinger/aza-Wittig/cyclization and their HIV-RT inhibitory
           activity
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Jie Shao, Mo Zhu, Ligang Gao, Hua Chen, Xiaoliu Li
      Azasugar aldehydes 6a and 6b containing azido groups were prepared from D-mannose. Three novel tetracyclic azasugars fused benzo[e][1,3]thiazin-4-one 9a -1, 9a-2 and 9a-3 were conveniently synthesized from 6a by the tandem intramolecular Staudinger/aza-Wittig/cyclization reaction under microwave radiation. Two unexpected elimination compounds 8b-1 and 8b-2 were achieved as the main products from 6b in the same processes. The newly synthesized azasugars were examined for their HIV reverse transcriptase (RT) inhibitory activities. The results showed that all the tested compounds could effectively inhibit RT activity. Among them, compound 8b-1 with the protective group (isopropylidene group) was the best one with the IC50 value of 0.76 μM. The structure activity relationship analysis suggested that improvement of the molecular hydrophilicity might be beneficial for their anti-HIV RT activities.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Structural analysis of the O-polysaccharide from the lipopolysaccharide of
           Pseudomonas putida BIM B-1100
    • Abstract: Publication date: Available online 25 December 2017
      Source:Carbohydrate Research
      Author(s): Evelina L. Zdorovenko, Alexander S. Shashkov, Alexandra A. Kadykova, Elena P. Kiseleva, Victoria V. Savich, Galina I. Novik, Yuriy A. Knirel
      Two specific polysaccharides, together with an →4)-α-d-Glcp-(1→ glucan (bacterial glycogen), were obtained from a lipopolysaccharide preparation isolated from the bacterium Pseudomonas putida BIM B-1100 by phenol/water extraction. The following structures of the polysaccharides were established by composition analysis, Smith degradation, ESI-MS, and 1D and 2D NMR spectroscopy: Image 2
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Cloning, purification and biochemical characterization of two
           β-N-acetylhexosaminidases from the mucin-degrading gut bacterium
           Akkermansia muciniphila
    • Abstract: Publication date: Available online 23 December 2017
      Source:Carbohydrate Research
      Author(s): Meng Wang, Xiao-Yang Zhang, Rui-Rui Guo, Zhi-Peng Cai, Xiao-Chun Hu, Huan Chen, Shuang Wei, Josef Voglmeir, Li Liu
      Two genes encoding the β-N-acetylhexosaminidases Am2301 and Am2446 were cloned successfully from the mucin-degrading bacterium Akkermansia muciniphila. The recombinant enzymes with molecular masses of 61 kDa and 78 kDa were isolated and biochemically characterised. The optimum temperature of both enzymes was 37 °C, and the optimum pH was determined to be pH 5.0 for Am2301 and pH 6.5 for Am2446. The addition of sodium dodecyl sulphate (SDS) reduced the enzymes' activity significantly. Cu2+-ions decreased the activity of Am2301 by 70%, while the activity of Am2446 was significantly reduced by Fe3+-ions. PugNAc strongly inhibited both enzymes already in the sub-molar concentration range. The enzymes catalysed the hydrolysis of β1,4-linked N-acetylgalactosamine and β1,6-linked N-acetylglucosamine from glycan standards, as well as β1,2-linked N-acetylglucosamine units from the non-reducing end of N-glycans. The present study describes the first functional characterisation of β-N-acetylhexosaminidases from this human gut symbiont.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Chondroitin sulfate-stabilized silver nanoparticles: Improved synthesis
           and their catalytic, antimicrobial, and biocompatible activities
    • Abstract: Publication date: Available online 14 December 2017
      Source:Carbohydrate Research
      Author(s): Jenn-jong Young, Kuang-ming Cheng, Yen-an Young, Xin-an Chen, Yu-hao Chen, Tein-yao Chang, Hui-ju Yen, Cheng-cheung Chen
      Herein, we describe an improved procedure for the green synthesis of chondroitin sulfate stabilized silver nanoparticles (ChS-AgNPs). Glucose was used as a reducing agent under alkaline conditions to obtain a small particle size (<10 nm), and the reduction was complete within 1 h at room temperature. The concentration of NaOH affected the reaction rate, formation yield, and particle size of ChS-AgNPs. The formation of AgNPs was confirmed using UV–vis, TEM, XRD, and XPS. ChS-AgNPs showed excellent catalytic activities in the reduction of 4-nitrophenol by NaBH4, and the reaction rate increased linearly with increasing catalyst amounts. The antimicrobial activities of ChS-AgNPs against A. baumannii (including multidrug-resistant strains), E. coli, P. aeruginosa, and S. aureus were evaluated using the broth microdilution method. Finally, from the morphological observations and cell cycle analysis of L929 cells, we found that ChS-AgNPs exhibited antimicrobial and biocompatible activities.
      Graphical abstract image

      PubDate: 2017-12-26T18:14:06Z
       
  • Structure and genetics of the O-specific polysaccharide of Escherichia
           coli O27
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Andrei V. Perepelov, Tingting Chen, Sofya N. Senchenkova, Andrei V. Filatov, Jingjie Song, Alexander S. Shashkov, Bin Liu, Yuriy A. Knirel
      The O-specific polysaccharide (O-antigen) is a part of the lipopolysaccharide on the cell surface of Gram-negative bacteria. The O-polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O27 and studied by sugar analysis and Smith degradation along with 1H and 13C NMR spectroscopy. The following structure of the branched hexasaccharide repeating unit was established, which is unique among known structures of bacterial polysaccharides: Image 2 where GlcA is non-stoichiometrically O-acetylated at position 3 (∼22%) or 4 (∼37%). Functions of genes in the O-antigen gene cluster of E. coli O27 were tentatively assigned by comparison with sequences in the available databases and found to be consistent with the O-polysaccharide structure.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • A highly regular fucan sulfate from the sea cucumber Stichopus horrens
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Nadezhda E. Ustyuzhanina, Maria I. Bilan, Andrey S. Dmitrenok, Elizaveta Yu. Borodina, Nikolay E. Nifantiev, Anatolii I. Usov
      A highly regular fucan sulfate SHFS was isolated from the sea cucumber Stichopus horrens by extraction of the body walls in the presence of papain followed by ion-exchange and gel permeation chromatography. SHFS had MW of about 140 kDa and contained fucose and sulfate in the molar ratio of about 1:1. Chemical and NMR spectroscopic methods were applied for the structural characterization of the polysaccharide. SHFS was shown to have linear molecules built up of 3-linked α-l-fucopyranose 2-sulfate residues. Anticoagulant properties of SHFS were assessed in vitro in comparison with the LMW heparin (enoxaparin) and totally sulfated 3-linked α-l-fucan. SHFS was found to have the lowest activity, and hence, both sulfate groups at O-2 and O-4 of fucosyl units seem to be important for anticoagulant effect of sulfated homo-(1 → 3)-α-l-fucans.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Synthesis of the repeating unit of O-specific polysaccharide isolated from
           the water-borne bacteria Aeromonas bestiarum 207
    • Abstract: Publication date: 1 February 2018
      Source:Carbohydrate Research, Volume 456
      Author(s): Yiren Xu, Guanghui Zong, Shuhui Jin, Jianjun Zhang
      Aeromonas bestiarum 207 is a bacterial pathogen with severe impact on aquaculture. In a recent study, the structure of OPS antigens from Aeromonas bestiarum was identified as pentasaccharide repeating units. Synthesis of the pentasaccharide repeating unit and its derivative are reported. Stereo- and regio-specific synthesis was achieved under Schmidt glycosylation conditions employing appropriately protected L-rhamopyranosyl and D-glucopyranosylamine building blocks. The pentasaccharide synthesis was achieved using a [3 + 2] strategy with an overall yield of 5.2% through 11 linear steps from the monosaccharide building blocks 10 and 14.
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      PubDate: 2017-12-13T05:07:35Z
       
  • Microfluidic reactor for lipase-catalyzed regioselective synthesis of
           
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Lihua Du, Zhipeng Jiang, Liangliang Xu, Nani Zhou, Jiahong Shen, Zhen Dong, Le Shen, Hong Wang, Xiping Luo
      Lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives was performed by Lipase TL IM from Thermomyces lanuginosus in a continuous-flow microreactor and then their antimicrobial activity was studied. It appears that neohesperidin, neohesperidin dihydrochalcone with primary OH on the sugar part is the most reactive substrate. Various reaction parameters were investigated including substrate molar ratio, reaction time and temperature. Maximum conversion (92%) was obtained under the optimal condition of substrate molar ratio of 8:1 (vinyl esters: neohesperidin) at 52 °C for about 35 min. Then, the antibacterial activity of modified neohesperidin ester derivatives was examined and showed great improvement against gram negative and gram positive bacteria.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Synthesis of aromatic and indole alpha-glucosinolates
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Quan V. Vo, Simone Rochfort, Pham C. Nam, Tuan L. Nguyen, Trung T. Nguyen, Adam Mechler
      Aromatic and indole glucosinolates are important members of the glucosinolate family of compounds du to their potential medicinal properties. They are known to exert antioxidant and anti-carcinogenic activity either by the natural products themselves, or their metabolic products including indole-3-carbinol and isothiocyanates. Natural glucosinolates are all β-glucosinolates; however, α-glucosinolates are also promising compounds for medicinal applications and hence have to be produced synthetically for any bio-activity studies. Here we report on the successful synthesis of a series of α-glucosinolates: α-neoglucobrassicin, α-4-methoxyglucobrassicin, 2,3-dichlorophenyl-α-glucosinolate for the first time. Testing for anti-inflammatory properties of these synthetic GLs, however, did not yield the expected activity.
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      PubDate: 2017-12-13T05:07:35Z
       
  • Сonformational study of persulfated propyl glucuronide
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Alexey G. Gerbst, Dmitry Z. Vinnitsky, Andrey S. Dmitrenok, Nadezhda E. Ustyuzhanina, Nikolay E. Nifantiev
      Glucuronic acid is an important constituting block of biologically active glycosaminoglycans where it can be present in non-sulfated, mono-sulfated and di-sulfated forms. Despite that some investigators reported previously that the exhaustively sulfated glucuronic acid moiety was characterized with unusual 1H-1H coupling constants and some times chemical shifts, these were just qualitative studies in which their authors suggested that the mentioned deviations in NMR spectra might mean complete inversion of the normal D-pyranoside chair conformation 4C1 to 1C4. Herein we outline a detailed conformational investigation showing that the distortion in the pyranoside ring of the persulfated glucuronic acid cannot be described simply with 4C1↔1C4 inversion. Instead, the experimental NOE data clearly indicate that two skew-boat conformers, OS2 and 3S1, provide significant contribution to the conformational equilibrium.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Hafnium(IV) triflate as a potent catalyst for selective 1-O-deacetylation
           of peracetylated saccharides
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Rui Wang, Ji-Zong Chen, Xiu-An Zheng, Rui Kong, Shan-Shan Gong, Qi Sun
      An efficient method for selective anomeric deacetylation of peracetylated mono-, di-, and trisaccharides has been developed by using 2 mol% Hf(OTf)4 as catalyst in acetonitrile. Employment of ultrasonic irradiation could significantly accelerate the reaction rate. Mechanistic study confirmed the hydrolysis nature of this reaction, and NMR experimental data suggested that multiple peracetylated saccharide molecules may ligate to Hf(IV) cation primarily via the anomeric acetate to promote its specific hydrolysis.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Penicillium purpurogenum produces a novel endo-1,5-arabinanase, active on
           debranched arabinan, short arabinooligosaccharides and on the artificial
           substrate p-nitrophenyl arabinofuranoside
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Felipe Vilches, María Cristina Ravanal, Felipe Bravo-Moraga, Danilo Gonzalez-Nilo, Jaime Eyzaguirre
      Penicillium purpurogenum secretes numerous lignocellulose-degrading enzymes, including four arabinofuranosidases and an exo-arabinanase. In this work, the biochemical properties of an endo-arabinanase (ABN1) are presented. A gene, coding for a potential ABN was mined from the genome. It includes three introns. The cDNA is 975 bp long and codes for a mature protein of 324 residues. The cDNA was expressed in Pichia pastoris. The enzyme is active on debranched arabinan and arabinooligosaccharides. In contrast to other characterized ABNs, inactive on p-nitrophenyl-α-L-arabinofuranoside (pNPAra), ABN1 is active on this substrate. The enzyme has an optimal pH of 4.5 and an optimal temperature of 30–35 °C. Calcium does not activate ABN1. ABN1 belongs to GH family 43 sub-family 6, and a Clustal alignment with sequences of characterized fungal ABNs shows highest identity (54.6%) with an ABN from Aspergillus aculeatus. A three-dimensional model of ABN1 was constructed and the docking with pNPAra was compared with similar models of an enzyme very active on this substrate and another lacking activity, both from GH family 43. Differences in the number of hydrogen bonds between enzyme and substrate, and distance between the substrate and the catalytic residues may explain the differences in activity shown by these enzymes.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Pyranose ring puckering in aldopentoses, ketohexoses and deoxyaldohexoses.
           A molecular dynamics study
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Karina Panczyk, Wojciech Plazinski
      Conformation of monosaccharides, including the ring shape, has for years been the subject of intensive research. Although d-aldohexopyranoses are the most extensively studied pyranoses, there also exist other groups of saccharides that contain analogous chemical system of the six-membered ring. Here we describe in details the results of the molecular dynamics-based conformational analysis concerning a series of pyranoses, namely: d-aldopentoses, d-ketohexoses as well as deoxy- (d-quinovose, l-fucose, l-rhamnose) and dideoxy- (abequose, paratose, tyvelose, digitoxose) derivatives of aldohexoses. By using the carbohydrate-dedicated GROMOS 56a6CARBO force field, we determined the conformational properties of both the lactol and hydroxymethyl groups as well as the anomeric populations for all considered compounds. The orientation of the lactol group follows the trend expected on the basis of the exo-anomeric effect for all compounds whereas the conformation of the hydroxymethyl group in d-ketohexoses is represented by the two gauche (with respect to the ring oxygen atom) rotamers. The special emphasis is put on the ring-inversion properties studied in the context of both the full chair-chair inversion and the chair-boat/skew-boat rearrangement. The calculated ring-distortion energies, compared with those obtained for regular d-aldohexopyranoses allowed for estimating the influence of particular substituents on the ring flexibility. Overall, such influence is correlated with the dimension of the substituent and its orientation but is limited to the case of the chair-chair inversion whereas the chair-to-boat/skew-boat rearrangement exhibits roughly the same properties for all pyranoses. For all d-aldopyranoses the α anomers exhibit lower ring-inversion free energies in comparison to the β anomers whereas this trend is inverted in the case of d-ketohexopyranoses.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • A combined variable temperature 600 MHz NMR/MD study of the calcium
           release agent cyclic adenosine diphosphate ribose (cADPR): Structure,
           conformational analysis, and thermodynamics of the conformational
           equilibria
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Uroš Javornik, Janez Plavec, Baifan Wang, Steven M. Graham
      A combined variable temperature 600 MHz NMR/molecular dynamics study of the Ca2+-release agent cyclic adenosine 5′-diphosphate ribose (cADPR) was conducted. In addition to elucidating the major and minor orientations of the conformationally flexible furanose rings, γ– (C4′–C5′), and β– (C5′–O5′) bonds, the thermodynamics (ΔH o, ΔS o) associated with each of these conformational equilibria were determined. Both furanose rings were biased towards a south conformation (64–74%) and both β–bonds heavily favored trans conformations. The R-ring γ–bond was found to exist almost exclusively as the γ+ conformer, whereas the A-ring γ–bond was a mixture of the γ+ and γt conformers, with the trans conformer being slightly favored. Enthalpic factors accounted for most of the observed conformational preferences, although the R-ring furanose exists as its major conformation based solely on entropic factors. There was excellent agreement between the NMR and MD results, particularly with regard to the conformer identities, but the MD showed a bias towards γ+ conformers. The MD results showed that both N-glycosidic χ–bonds are exclusively syn. Collectively the data allowed for the construction of a model for cADPR in which many of the conformationally flexible units in fact effectively adopt single orientations and where most of the conformational diversity resides in its A-ring furanose and γ–bond.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • DIDMH in combination with triflic acid - A new promoter system for
           thioglycoside glycosyl donors
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Mads Heuckendorff, Henrik H. Jensen
      We have explored the possibility of using 1,3-diiodo-5,5-dimethylhydantoin (DIDMH) as an alternative to N-iodosuccinimide (NIS) for activation of glycosyl donors of the thioglycoside type in various glycosylation reactions. DIDMH was found to match NIS when it comes to the capability to activate thioglycosides and provide glycosylation products in good yields. Notably, with the two equivalents of reactive iodonium ions per molecule of DIDMH less mass needs to be added making this activator a more atom economically alternative to NIS. Furthermore, DIDMH was found to be stable upon storage for weeks and comparably priced to NIS. With this knowledge in hand we therefore encourage the carbohydrate community to consider using DIDMH for activation of thioglycosides in glycosylation reactions.
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      PubDate: 2017-12-13T05:07:35Z
       
  • Developing cellulosic waste products as platform chemicals: protecting
           group chemistry of α-glucoisosaccharinic acid
    • Abstract: Publication date: 2 January 2018
      Source:Carbohydrate Research, Volume 455
      Author(s): Michael Almond, Mustapha G. Suleiman, Matthew Hawkins, Daniel Winder, Thomas Robshaw, Megan Waddoups, Paul N. Humphreys, Andrew P. Laws
      Alpha and beta-glucoisosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) which are produced when cellulosic materials are treated with aqueous alkali are potentially valuable platform chemicals. Their highly functionalised carbon skeleton, with fixed chirality at C-2 and C-4, makes them ideal starting materials for use in synthesis. In order to assess the potential of these saccharinic acids as platform chemicals we have explored the protecting group chemistry of the lactone form of alpha-glucoisosaccharinic acid (α-GISAL). We report here the use of single and multiple step reaction pathways leading to the regioselective protection of the three different hydroxyl groups of α-GISAL. We report strategies for protecting the three different hydroxyl groups individually or in pairs. We also report the synthesis of a range of tri-O-protected α-GISAL derivatives where a number of the products contain orthogonal protecting groups.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Arabinofuranose 1,2,5-orthobenzoate as a single precursor of linear
           α(1 → 5)-linked oligoarabinofuranosides
    • Abstract: Publication date: Available online 8 December 2017
      Source:Carbohydrate Research
      Author(s): Maria V. Panova, Nikita M. Podvalnyy, Eugene L. Okun, Polina I. Abronina, Alexander O. Chizhov, Leonid O. Kononov
      Selectively protected mono-, di- and trisaccharide thioglycoside building blocks with unprotected primary hydroxy group at the non-reducing end, available in only one step from 3-O-benzoyl β-d-arabinofuranose 1,2,5-orthobenzoate, were used in the synthesis of linear α(1 → 5)-linked oligoarabinofuranosides up to octasaccharide. The obtained oligosaccharides contain 4-(2-chloroethoxy)phenyl (CEP) or 4-(2-azidoethoxy)phenyl (AEP) pre-spacer aglycons that allow preparation of neoglycoconjugates.
      Graphical abstract image

      PubDate: 2017-12-13T05:07:35Z
       
  • Structural and immunological characterization of a glycoconjugate based on
           the delipidated lipopolysaccharide from a nontypeable Helicobacter pylori
           strain PJ1 containing an extended d-glycero-d-manno-heptan
    • Abstract: Publication date: Available online 7 December 2017
      Source:Carbohydrate Research
      Author(s): Eleonora Altman, Vandana Chandan, Blair A. Harrison, Evgeny Vinogradov
      Structural characterization of the lipopolysaccharide (LPS) from a nontypeable Helicobacter pylori strain PJ1 and two corresponding mutants, PJ1 HP1283:cam and PJ1 HP1284:cam, was performed using a combination of NMR and mass spectrometric techniques. It resulted in the core structure that differed significantly from the one proposed previously. Overall architecture of PJ1 LPS was found to be consistent with a structural model described for several other H. pylori strains. It contained a polymer of d-glycero-d-manno-heptose (dd-Hep) as the O-chain component, linked to α-1,6-glucan through a dd-Hep oligosaccharide. H. pylori PJ1 HP1283:cam LPS was missing dd-heptan, terminating with an α-1,6-glucan chain containing 5–13 glucose residues. LPS of strain PJ1 HP1284:cam was missing dd-Hep from the core and had β-GlcNAc attached directly to O-3 of the inner-core ld-Hep residue. To investigate the role of dd-heptan in protective immunity, delipidated LPS (dLPS) from strain PJ1 was conjugated to tetanus toxoid (TT) and immunological properties of the resultant glycoconjugate dLPS(PJ1)-TT - determined. The dLPS(PJ1)-TT conjugate was immunogenic in mice and rabbits and induced specific and cross-reactive functional antibodies against homologous and heterologous strains of H. pylori. Whole cell indirect ELISA performed on a selected number of H. pylori isolates confirmed that the immune response correlated with the presence of α-1,6-glucan and was not augmented by the dd-Hep content of these strains.
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      PubDate: 2017-12-13T05:07:35Z
       
  • Graphical contents list
    • Abstract: Publication date: 1–14 December 2017
      Source:Carbohydrate Research, Volumes 453–454


      PubDate: 2017-12-13T05:07:35Z
       
  • A concise synthesis of rhamnan oligosaccharides with alternating
           α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages by iterative
           α-glycosylation using disaccharide building blocks
    • Abstract: Publication date: Available online 14 November 2017
      Source:Carbohydrate Research
      Author(s): Hidenori Tanaka, Yu Hamaya, Nagatoshi Nishiwaki, Hideharu Ishida
      A concise synthetic route to rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages is reported. This synthesis was achieved by iterative α-glycosylation using disaccharide building blocks and through orthogonal coupling between thioglycosides of L-rhamnose. To investigate the detailed structure-activity relationship of rhamnan sulfate from Monostroma nitidum against herpes simplex virus type 2, the synthesized oligosaccharides, bearing different orthogonal protecting groups (i.e., benzoyl, benzyl, 2-naphthylmethyl, and/or p-methoxybenzyl) are expected to be suitable for conversion into a range of rhamnan structures with diverse sulfation patterns.
      Graphical abstract image

      PubDate: 2017-11-16T12:19:17Z
       
  • Chemo-enzymatic synthesis of the glucagon containing N-linked
           oligosaccharide and its characterization
    • Abstract: Publication date: Available online 13 November 2017
      Source:Carbohydrate Research
      Author(s): Takayuki Higashiyama, Midori Umekawa, Masaya Nagao, Toshihiko Katoh, Hisashi Ashida, Kenji Yamamoto
      The chemo-enzymatic synthesis of an artificially N-glycosylated derivative of glucagon, a peptide hormone that regulates the blood sugar level, is described. We synthesized the glycosylated glucagon by chemical synthesis of an N-acetylglucosaminyl peptide and enzymatic transfer of an oligosaccharide using the transglycosylation activity of the glycosynthase-like mutant of Mucor hiemalis endo-β-N-acetylglucosaminidase (Endo-M) and sialo-oligosaccharide oxazoline as a donor substrate. The sialo-oligosaccharide-attached glucagon synthesized showed high resistance against protease degradation and stimulated the release of glucose from mouse hepatocytes when added to cells. The synthetic glucagon showed slightly higher activity than native glucagon and has potential as a therapeutic agent for treating diabetic patients.
      Graphical abstract image

      PubDate: 2017-11-16T12:19:17Z
       
  • Role of 6-O-α-maltosyl-β-cyclodextrin in lysosomal cholesterol
           deprivation in Npc1-deficient Chinese hamster ovary cells
    • Abstract: Publication date: Available online 10 November 2017
      Source:Carbohydrate Research
      Author(s): Yasuyo Okada, Erika Ueda, Yuki Kondo, Yoichi Ishitsuka, Tetsumi Irie, Taishi Higashi, Keiichi Motoyama, Hidetoshi Arima, Muneaki Matuso, Katsumi Higaki, Kousaku Ohno, Junichi Nishikawa, Atsushi Ichikawa
      We aimed to investigate whether 6-O-α-maltosyl-β-cyclodextrin (Mal-βCD) is incorporated into cells and lysosomes during the release of unesterified cholesterol in Npc1-deficient Chinese hamster ovary (CHO) cells (Npc1 KO cells) and CHO-JP17 cells (JP17 cells). Internalization of Mal-βCD in cells and lysosomes and extracellular release of lysosomal unesterified cholesterol were demonstrated by LC/MS/MS and LC/MS, respectively. Internalization of Mal-βCD was greater in Npc1 KO cells than in JP17 cells. The majority of internalized Mal-βCD in both cell types was metabolized by lysosomal α-glucosidase to 6-O-α-D-glucosyl-β-cyclodextrin (Glc-βCD). However, Mal-βCD did not directly enter the lysosomes prepared from cell homogenates. Mal-βCD-treated Npc1 KO cells and JP17 cells both released Mal-βCD and Glc-βCD, together with unesterified cholesterol, out of cells. The release of unesterified cholesterol by Mal-βCD in Npc1 KO cells was much greater than that in JP17 cells. This study is the first to report the influx of Mal-βCD into the lysosomes of Npc1 KO cells and JP17 cells, followed by generation of Glc-βCD, and the efflux of Mal-βCD/Glc-βCD and unesterified cholesterol to the extracellular fluid, based on the quantitative LC/MS analysis.
      Graphical abstract image

      PubDate: 2017-11-16T12:19:17Z
       
  • Synthesis of substrate analogues as potential inhibitors for Mycobacterium
           tuberculosis enzyme MshC
    • Abstract: Publication date: 1–14 December 2017
      Source:Carbohydrate Research, Volumes 453–454
      Author(s): Krishnakant Patel, Fengling Song, Peter R. Andreana
      Mycothiol cysteine ligase (MshC) is a key enzyme in the mycothiol (MSH) biosynthesis and a promising target for developing new anti-mycobacterial compounds. Herein, we report on the synthesis of substrate analogues, as potential inhibitors, for the MshC enzyme. The target molecules were synthesized employing a Schmidt glycosylation strategy using an enantiomerically pure inositol acceptor and 2-deoxy trichloroacetimidate glycosyl donors with glycosylation yields greater than 70% and overall yields >5%. The inositol acceptor was obtained via chiral resolution of (±)-myo-inositol.
      Graphical abstract image

      PubDate: 2017-11-09T07:26:15Z
       
  • Isolation and characterisation of an unexpected byproduct in the
           regioselective butane diacetal protection of α-methyl galactopyranoside
    • Abstract: Publication date: Available online 6 November 2017
      Source:Carbohydrate Research
      Author(s): Clément Q. Fontenelle, Ramakrishna Kuppala, Mark Light, Bruno Linclau
      The regioselective protection of both methyl galactopyranoside anomers at the 2 and 3-positions as the butane diacetal (BDA) is well known. Here we describe the formation of an unexpected byproduct, which mainly occurs when α-methyl galactopyranoside is reacted with 2,3-butanedione under BF3•OEt2 catalysis. The structure of the byproduct, which did not arise from anomerisation to the β-anomer or from BDA formation at the galactopyranoside 3,4-positions, was elucidated by NMR and X-ray crystallographic analysis, and proved to be the expected BDA protected galactopyranoside, but in which the stereochemistry of both its BDA acetal centres are inverted. Interestingly, the conformation of the resulting six-membered BDA ring was distorted to a skew boat conformation in order to maintain anomeric stabilisation.
      Graphical abstract image

      PubDate: 2017-11-09T07:26:15Z
       
  • Synthesis of 3-aminopropyl β-(1 → 6)-d-glucotetraoside and its
           biotinylated derivative
    • Abstract: Publication date: Available online 6 November 2017
      Source:Carbohydrate Research
      Author(s): Dmitry V. Yashunsky, Alexander A. Karelin, Yury E. Tsvetkov, Nikolay E. Nifantiev
      3-Aminopropyl β-(1 → 6)-d-glucotetraoside has been synthesized from 3-benzyloxycarbonylaminopropanol and 6-O-acetyl-2,3,4-tri-O-benzoyl-d-glucopyranosyl trichloroacetimidate by successive attachment of one monosaccharide unit in total yield of 22%. Free aminopropyl glycoside was converted into a biotin derivative that can be used for controlled immobilization of the oligosaccharide on streptavidin-coated ELISA plates and for tracing carbohydrate binding molecules.
      Graphical abstract image

      PubDate: 2017-11-09T07:26:15Z
       
  • Tandem mass spectrometry of fucoidan-derived fragments, labeled with
           heavy-oxygen
    • Abstract: Publication date: Available online 4 November 2017
      Source:Carbohydrate Research
      Author(s): Stanislav D. Anastyuk, Natalia M. Shevchenko, Kristina V. Belokozova, Pavel S. Dmitrenok
      A procedure for the partial depolymerization of sulfated fucans and selective labeling with 18O was developed. A tandem electrospray ionization mass spectrometry (ESI MS/MS) was applied for the direct analysis of mixtures of structurally-different oligosaccharides, derived from the fucoidans of known structure. The presence of label allowed unambiguous distinguishing between the fragment ions of 0,2X0-type at m/z 287 and 2,4A-type at m/z 285, since 18O at the reducing end gave +2 mass shifting. Thus, ESI MS/MS was able to detect (1,2)-type of linkage in disaccharides from the fucoidan of brown alga S. cichorioides for the first time. It was also discovered that 2,4A-type fragments in 4-linked disaccharides that were incorrectly assigned to 0,2X-type previously, suggested, probably, substitution at C-4 in mono- and disaccharide fragments, derived from the fucoidan of the brown alga F. evanescens.
      Graphical abstract image

      PubDate: 2017-11-09T07:26:15Z
       
  • Supramolecular glycorhodamine-polymer dot ensembles for the homogeneous,
           fluorogenic analysis of lectins
    • Abstract: Publication date: Available online 1 November 2017
      Source:Carbohydrate Research
      Author(s): Chang-Zheng Wang, Xiao-Peng He
      We have developed a new series of glycoprobe-polymer dot ensembles for the fluorogenic, homogeneous detection of lectins. Electrostatic self-assembly between positively charged rhodamine-based glycosides and negatively charged poly(3-hexylthiophene-2,5-diyl)/poly(styrene-co-maleic anhydride) polymer dots produces the ensembles with a quenched fluorescence. Fluorescence spectroscopy showed that the ensembles exhibited a concentration-dependent fluorescence enhancement with selective lectins over a range of unselective lectins and proteins. This research provides insight into the development of simple fluorogenic probes for homogeneous lectin analyses based on the supramolecular assembly between polymeric nanoparticles and fluorescent glycoprobes.
      Graphical abstract image

      PubDate: 2017-11-02T07:01:48Z
       
  • Mannosylcalix[n]arenes as multivalent ligands for DC-SIGN
    • Abstract: Publication date: Available online 31 October 2017
      Source:Carbohydrate Research
      Author(s): Ilaria Morbioli, Vanessa Porkolab, Andrea Magini, Alessandro Casnati, Franck Fieschi, Francesco Sansone
      DC-SIGN is a receptor protruded from the membrane of immature dendritic cells (DCs) that participates in the activation of the immune response through the recognition of pathogen-associated molecular patterns (PAMPs). On the other hand, HIV exploits the interaction between high-mannose structures of its envelope glycoprotein gp120 and DC-SIGN to be transported towards and infect T-cells. DC-SIGN is involved in the recognition process in the form of a tetramer and the multiple exposition of carbohydrate recognition sites (CRSs) is amplified by the formation on the DCs membrane of patches of tetramers. DC-SIGN is then considered an interesting target to fight the virus and multivalent systems exposing multiple copies of ligating units for its CRSs are becoming valuable tools to reach this goal. We herein prepared four mannosylated calix[n]arenes (1a-d) and tested them by Surface Plasmon Resonance (SPR) competition assays as inhibitors of the binding between DC-SIGN and a mannosylated BSA used as model of HIV gp120. IC50s in the μM range were found evidencing in particular for compound 1a that, although rather moderate, a multivalent effect is taking place in the inhibition activity of this cluster. A relative potency (rp/n) around 4, respect to the monovalent methyl α-mannoside and normalized for the number of monosaccharide on the scaffold, was observed. This result, compared with previously reported data relative to dendrimers with the same valency, indicates the calixarene as a promising scaffold to build efficient inhibitors for DC-SIGN and, in perspective, for HIV.
      Graphical abstract image

      PubDate: 2017-11-02T07:01:48Z
       
  • The Shewanella woodyi galactokinase pool phosphorylates glucose at the
           6-position
    • Abstract: Publication date: Available online 31 October 2017
      Source:Carbohydrate Research
      Author(s): Louis Patrick Conway, Fang Fang Liu, Qian Li, Josef Voglmeir
      Galactokinases are a class of enzymes which belong to the GHMP (galactokinase, homoserine kinase, mevalonate kinase, and phosphomevalonate kinase) superfamily and catalyse the phosphorylation of galactose in the first step of the Leloir pathway. Here we report the discovery of three enzymes from Shewanella woodyi which have been classified as galactokinases based on sequence similarity. However, each of these enzymes show little to no significant activity towards galactose and instead exhibit a strong preference for glucose. Furthermore, in contrast to the usual galactose-1-phosphate product of the galactokinase-catalysed reaction, these enzymes produce glucose-6-phosphate. This radical change in enzyme functionality is postulated to be linked to the mutation of a glycine residue which is conserved in all other sequenced galactokinases.
      Graphical abstract image

      PubDate: 2017-11-02T07:01:48Z
       
  • Overview on the antiviral activities and mechanisms of marine
           polysaccharides from seaweeds
    • Abstract: Publication date: Available online 31 October 2017
      Source:Carbohydrate Research
      Author(s): Qimin shi, Anjian Wang, Zhonghua Lu, Chunjun Qin, Jing Hu, Jian Yin
      Marine polysaccharides are attracting increasing attention in medical and pharmaceutical development because of their important biological properties. The seaweed polysaccharides have now become a rich resource of potential antiviral drugs due to their antiviral activities against various viruses. The structural diversity and complexity of marine polysaccharides and their derivatives contribute to their antiviral activities in different phases of many different viral infection processes. This review mainly introduces the different types of seaweed polysaccharides and their derivatives with potent antiviral activities. Moreover, the antiviral mechanisms and medical applications of certain marine polysaccharides from seaweeds are also demonstrated.
      Graphical abstract image

      PubDate: 2017-11-02T07:01:48Z
       
  • Effect of sucralose on the enzyme kinetics of invertase using real-time
           NMR spectroscopy and progress curve analysis
    • Abstract: Publication date: Available online 31 October 2017
      Source:Carbohydrate Research
      Author(s): Cheenou Her, Jaideep Singh, V.V. Krishnan
      Sucralose, a derivative of sucrose, is widely used in noncaloric artificial sweeteners (NAS). Contrary to the belief that sucralose is physiologically inert and a healthy alternative sweetener to natural sugar, emerging studies indicate that sucralose alters the host metabolism as well as the composition of the microbiome. In this manuscript, we use real-time nuclear magnetic resonance (NMR) spectroscopy to demonstrate that sucralose alters the enzymatic conversion of sucrose to glucose and fructose. The real-time NMR progress curve analysis suggests that sucralose has the characteristic of a competitive inhibitor on the kinetics of the enzymatic process. This affects the rate of glucose production, and thus indirectly affecting the mutarotation process of α-D-glucose to β-D-glucose conversion. At a 1:2 molar ratio of sucrose to sucralose, the results show that the catalytic efficiency of the enzyme is reduced by more than 50% in comparison to the measurements without sucralose. Altogether, as sucralose alters the rate of glucose production, sucralose cannot be considered inert to the metabolism as several downstream events in both prokaryotic and eukaryotic systems strongly depend on the rate of glucose metabolism.
      Graphical abstract image

      PubDate: 2017-11-02T07:01:48Z
       
  • Properties of two fungal endo-β-1,3-galactanases and their synergistic
           action with an exo-β-1,3-galactanase in degrading
           arabinogalactan-proteins
    • Abstract: Publication date: Available online 25 October 2017
      Source:Carbohydrate Research
      Author(s): Yoshihisa Yoshimi, Kaori Yaguchi, Satoshi Kaneko, Yoichi Tsumuraya, Toshihisa Kotake
      Arabinogalactan-proteins (AGPs) are plant proteoglycans, which are widely encountered in the plant kingdom, usually localized on the cell surface. The carbohydrate moieties of AGPs consist of β-1,3-galactan main chains and β-1,6-galactan side chains, to which other auxiliary sugars are attached. To date, FvEn3GAL isolated from Flammulina velutipes is the sole β-1,3-galactanase acting on β-1,3-galactan in an endo-manner. Here we cloned two homologous genes, designated Af3G and NcEn3GAL, possibly encoding endo-β-1,3-galactanase from Aspergillus flavus and Neurospora crassa, respectively. The recombinant Af3G (rAf3G) and rNcEn3GAL expressed in Pichia pastoris specifically hydrolyzed β-1,3-galactan in an endo-manner, as did the rFvEn3GAL. Among galactooligosaccharides, β-1,3-galactotriose was identified as the smallest substrate for these enzymes. These results suggest that enzymatic characteristics are conserved in many endo-β-1,3-galactanases belonging to the glycoside hydrolase 16 family. On the other hand, rAf3G and rNcEn3GAL generated more β-1,3-galactobiose from β-1,3-galactotetraose than did rFvEn3GAL, suggesting that rAf3G and rNcEn3GAL prefer hydrolyzing the central β-1,3-glycosidic linkage of three in β-1,3-galactotetraose. Although rAf3G and rNcEn3GAL alone hardly hydrolyze native AGP, they acted synergistically with a fungal exo-β-1,3-galactanase on the AGP. These endo-β-1,3-galactanases presumably aid hydrolysis by internally breaking up AGPs, which creates more sites of attack for exo-β-1,3-galactanase.
      Graphical abstract image

      PubDate: 2017-10-26T03:58:36Z
       
  • Concise synthesis of 2,7-anhydrosialic acid derivatives and its
           application
    • Abstract: Publication date: Available online 19 October 2017
      Source:Carbohydrate Research
      Author(s): Kesatebrhan Haile Asressu, Cheng-Chung Wang
      In N-acetylneuraminic acid, apart from O9 and O8, a possible glycosylation site is the O4 position. For example, gangliosides HLG-2 and HPG-7 are considered to be potential lead compounds for carbohydrate-based drug development to treat neural disorders. However, the construction of their α(1 → 4) fucosyl sialic acid and α(2 → 4) linkages between sialic acids is difficult because of the regioselectivity problem. Herein, N-acetyl-2,7-anhydroneuraminic acid was synthesized in three steps from Neu5Ac methyl ester through per-O-trimethylsilylation, heating-assisted intramolecular anomeric protection (iMAP) and desilylation. The iMAP simultaneously circumvents both the 2- and 7-OH protection. Upon protecting the 8- and 9-OH groups as a benzylidene acetal, only 4-OH is free for glycosylation. These 2,7-anhydro-8,9-O-benzylidenesialic acid derivatives were examined as acceptor for an α-selective fucosylation to construct the glycosidic linkage of fucosyl α(1 → 4) 2,7-anhydroneuraminic acid.
      Graphical abstract image

      PubDate: 2017-10-26T03:58:36Z
       
 
 
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