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  Subjects -> CHEMISTRY (Total: 848 journals)
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    - CHEMISTRY (602 journals)
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CHEMISTRY (602 journals)                  1 2 3 4 | 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: 25)
ACS Catalysis     Full-text available via subscription   (Followers: 29)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 16)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 23)
ACS Macro Letters     Full-text available via subscription   (Followers: 21)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 37)
ACS Nano     Full-text available via subscription   (Followers: 189)
ACS Photonics     Full-text available via subscription   (Followers: 7)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 20)
Acta Chemica Iasi     Open Access   (Followers: 1)
Acta Chimica Sinica     Full-text available via subscription  
Acta Chimica Slovaca     Open Access   (Followers: 1)
Acta Chromatographica     Full-text available via subscription   (Followers: 8)
Acta Facultatis Medicae Naissensis     Open Access  
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 5)
Acta Scientifica Naturalis     Open Access   (Followers: 1)
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 5)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 6)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 4)
Advanced Functional Materials     Hybrid Journal   (Followers: 45)
Advanced Science Focus     Free   (Followers: 3)
Advances in Chemical Engineering and Science     Open Access   (Followers: 52)
Advances in Chemical Science     Open Access   (Followers: 11)
Advances in Chemistry     Open Access   (Followers: 11)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 17)
Advances in Drug Research     Full-text available via subscription   (Followers: 22)
Advances in Enzyme Research     Open Access   (Followers: 6)
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: 16)
Advances in Nanoparticles     Open Access   (Followers: 12)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 14)
Advances in Polymer Science     Hybrid Journal   (Followers: 39)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 17)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 16)
Advances in Quantum Chemistry     Full-text available via subscription   (Followers: 5)
Advances in Science and Technology     Full-text available via subscription   (Followers: 7)
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)
Alchemy : Jurnal Penelitian 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: 65)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 14)
American Journal of Chemistry     Open Access   (Followers: 24)
American Journal of Plant Physiology     Open Access   (Followers: 12)
American Mineralogist     Full-text available via subscription   (Followers: 8)
Anadolu University Journal of Science and Technology     Open Access  
Analyst     Full-text available via subscription   (Followers: 42)
Angewandte Chemie     Hybrid Journal   (Followers: 138)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 188)
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: 3)
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: 12)
Annual Review of Food Science and Technology     Full-text available via subscription   (Followers: 14)
Anti-Infective Agents     Hybrid Journal   (Followers: 3)
Antiviral Chemistry and Chemotherapy     Hybrid Journal  
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 6)
Applied Spectroscopy     Full-text available via subscription   (Followers: 23)
Applied Surface Science     Hybrid Journal   (Followers: 23)
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: 3)
Australian Journal of Chemistry     Hybrid Journal   (Followers: 6)
Autophagy     Hybrid Journal   (Followers: 2)
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 9)
Biochemistry     Full-text available via subscription   (Followers: 243)
Biochemistry Insights     Open Access   (Followers: 5)
Biochemistry Research International     Open Access   (Followers: 6)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 9)
Bioinspired Materials     Open Access   (Followers: 3)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 2)
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: 10)
Biomedical Chromatography     Hybrid Journal   (Followers: 7)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 3)
BioNanoScience     Partially Free   (Followers: 4)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 110)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 98)
Bioorganic Chemistry     Hybrid Journal   (Followers: 10)
Biopolymers     Hybrid Journal   (Followers: 17)
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: 26)
Bulletin of the Korean Chemical Society     Hybrid Journal   (Followers: 1)
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: 8)
Canadian Mineralogist     Full-text available via subscription   (Followers: 3)
Carbohydrate Research     Hybrid Journal   (Followers: 26)
Carbon     Hybrid Journal   (Followers: 65)
Catalysis for Sustainable Energy     Open Access   (Followers: 5)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 7)
Catalysis Science and Technology     Free   (Followers: 6)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 3)
Catalysts     Open Access   (Followers: 6)
Cellulose     Hybrid Journal   (Followers: 5)
Cereal Chemistry     Full-text available via subscription   (Followers: 4)
ChemBioEng Reviews     Full-text available via subscription   (Followers: 1)
ChemCatChem     Hybrid Journal   (Followers: 7)
Chemical and Engineering News     Free   (Followers: 10)
Chemical Bulletin of Kazakh National University     Open Access  
Chemical Communications     Full-text available via subscription   (Followers: 70)
Chemical Engineering Research and Design     Hybrid Journal   (Followers: 22)
Chemical Research in Chinese Universities     Hybrid Journal   (Followers: 3)
Chemical Research in Toxicology     Full-text available via subscription   (Followers: 18)
Chemical Reviews     Full-text available via subscription   (Followers: 148)
Chemical Science     Open Access   (Followers: 19)
Chemical Technology     Open Access   (Followers: 13)
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: 25)
ChemInform     Hybrid Journal   (Followers: 7)
Chemistry & Biodiversity     Hybrid Journal   (Followers: 5)
Chemistry & Biology     Full-text available via subscription   (Followers: 30)
Chemistry & Industry     Hybrid Journal   (Followers: 4)
Chemistry - A European Journal     Hybrid Journal   (Followers: 124)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 14)
Chemistry and Materials Research     Open Access   (Followers: 15)
Chemistry Central Journal     Open Access   (Followers: 4)
Chemistry Education Research and Practice     Free   (Followers: 4)
Chemistry in Education     Open Access   (Followers: 3)
Chemistry International     Hybrid Journal   (Followers: 1)
Chemistry Letters     Full-text available via subscription   (Followers: 45)
Chemistry of Materials     Full-text available via subscription   (Followers: 159)
Chemistry of Natural Compounds     Hybrid Journal   (Followers: 9)
Chemistry-Didactics-Ecology-Metrology     Open Access  
ChemistryOpen     Open Access   (Followers: 2)
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: 8)
ChemPlusChem     Hybrid Journal   (Followers: 1)
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: 24)
Chromatography Research International     Open Access   (Followers: 5)
Clay Minerals     Full-text available via subscription   (Followers: 8)
Cogent Chemistry     Open Access  
Colloid and Interface Science Communications     Open Access  
Colloid and Polymer Science     Hybrid Journal   (Followers: 10)
Colloids and Surfaces B: Biointerfaces     Hybrid Journal   (Followers: 8)
Combinatorial Chemistry & High Throughput Screening     Hybrid Journal   (Followers: 3)
Combustion Science and Technology     Hybrid Journal   (Followers: 18)
Comments on Inorganic Chemistry: A Journal of Critical Discussion of the Current Literature     Hybrid Journal   (Followers: 1)
Composite Interfaces     Hybrid Journal   (Followers: 5)
Comprehensive Chemical Kinetics     Full-text available via subscription   (Followers: 2)
Comptes Rendus Chimie     Full-text available via subscription  
Comptes Rendus Physique     Full-text available via subscription   (Followers: 1)
Computational and Theoretical Chemistry     Hybrid Journal   (Followers: 9)
Computational Biology and Chemistry     Hybrid Journal   (Followers: 11)
Computational Chemistry     Open Access   (Followers: 2)
Computers & Chemical Engineering     Hybrid Journal   (Followers: 10)
Coordination Chemistry Reviews     Full-text available via subscription  
Copernican Letters     Open Access  
Critical Reviews in Biochemistry and Molecular Biology     Hybrid Journal   (Followers: 5)
Crystal Structure Theory and Applications     Open Access   (Followers: 2)
CrystEngComm     Full-text available via subscription   (Followers: 10)
Current Catalysis     Hybrid Journal   (Followers: 1)
Current Metabolomics     Hybrid Journal   (Followers: 3)
Current Opinion in Colloid & Interface Science     Hybrid Journal   (Followers: 8)
Current Opinion in Molecular Therapeutics     Full-text available via subscription   (Followers: 15)
Current Research in Chemistry     Open Access   (Followers: 8)
Current Science     Open Access   (Followers: 46)
Dalton Transactions     Full-text available via subscription   (Followers: 18)
Detection     Open Access   (Followers: 2)
Developments in Geochemistry     Full-text available via subscription   (Followers: 2)
Diamond and Related Materials     Hybrid Journal   (Followers: 11)
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: 5)
EDUSAINS     Open Access  
Elements     Full-text available via subscription   (Followers: 1)
Environmental Chemistry     Hybrid Journal   (Followers: 5)
Environmental Chemistry Letters     Hybrid Journal   (Followers: 2)

        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  [3040 journals]
  • Discrimination between naphthacene and triphenylene using cellulose
           tris(4-methylbenzoate) and cellulose tribenzoate: A computational study
    • Abstract: Publication date: Available online 7 January 2017
      Source:Carbohydrate Research
      Author(s): Yusuke Murakami, Tohru Shibata, Kazuyoshi Ueda
      The mechanisms of naphthacene and triphenylene discrimination using commercially available cellulose tris(4-methylbenzoate) (CMB) and cellulose tribenzoate (CB) chiral stationary phases were investigated using molecular mechanics calculations. Naphthacene and triphenylene could be separated by liquid chromatography on CMB and CB, with triphenylene being eluted earlier than naphthacene on both phases. However, the corresponding separation factor is much larger for CMB than for CB. The docking of these polycyclic aromatic hydrocarbons to the above polymers suggested that the most important sites of CMB and CB for interacting with these hydrocarbons are located at equivalent positions, featuring a space surrounded by main chain glucose units and benzoyl side chains. The difference of hydrocarbon stabilization energies with CMB and CB agreed well with the observed chromatographic separation factors.
      Graphical abstract image

      PubDate: 2017-01-13T08:43:52Z
       
  • The structure of the LPS O-chain of Fusobacterium nucleatum strain 25586
           containing two novel monosaccharides, 2-acetamido-2,6-dideoxy-l-altrose
           and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid
    • Abstract: Publication date: Available online 9 January 2017
      Source:Carbohydrate Research
      Author(s): Evgeny Vinogradov, Frank St. Michael, Andrew D. Cox
      Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. Recently, it has been gaining attention as a potential causative agent for colorectal cancer and is strongly linked with pregnancy complications including pre-term and still births. Little is known about the virulence factors of this organism, and thus we have initiated studies to examine the bacterium's surface glycochemistry. We isolated lipopolysaccharide (LPS) from F. nucleatum strain 25586 and purified and performed structural analysis on the O-antigen polysaccharide. The polysaccharide contained two novel sugars, 2-acetamido-2,6-dideoxy-l-altrose (l-6dAltNAc) and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid (Non5Am), which was tentatively assigned the l -glycero- l -gluco configuration. The polysaccharide was found to have a trisaccharide repeating unit, which is phosphorylated with phosphocholine (PCho), and the following structure was established: -[-4-β-Nonp5Am-4-α-l-6dAltpNAc3PCho-3-β-d-QuipNAc-]- We propose the trivial name ‘fusaminic acid’ for the novel nonulosonic acid. It is the first occurrence of a 9-deoxynonulosonic acid with a hydroxyl group at C-7, which is occupied by an amino group in all monosaccharides of this class described so far.
      Graphical abstract image

      PubDate: 2017-01-13T08:43:52Z
       
  • Isomelezitose formation by glucansucrases
    • Abstract: Publication date: Available online 11 January 2017
      Source:Carbohydrate Research
      Author(s): Gregory L. Côté, Christopher D. Skory
      Several glucansucrases were surveyed for their ability to produce isomelezitose, a trisaccharide with the structure α-D-glucopyranosyl (1 → 6) β-D-fructofuranosyl (2 ↔ 1) α-D-glucopyranoside. Nearly all strains tested, with one exception, produced at least trace levels of isomelezitose. Yields were low but significant, ranging from less than 1% to approximately 5% based on sucrose. This trisaccharide may arise in either of two ways: glucopyranosyl transfer to the 6Fru-OH position of sucrose, or to the anomeric OH position of isomaltulose. This study indicates that isomelezitose formation may be a general phenomenon of many glucansucrase reactions.
      Graphical abstract image

      PubDate: 2017-01-13T08:43:52Z
       
  • Large scale synthesis and regioselective protection schemes of ethyl
           2-azido-2-deoxy-1-thio-α-D-cellobioside for preparation of heparin
           thiodisaccharide building blocks
    • Abstract: Publication date: Available online 11 January 2017
      Source:Carbohydrate Research
      Author(s): Kevin Sheerin, Lorenzo Guazzelli, Stefan Oscarson
      Crystalline acetylated ethyl 2-azido-2-deoxy-1-thio-α-d-cellobioside has been prepared on a multigram scale from cellobiose in an overall yield of 23% with no chromatography required and converted after deacetylation into the 4′,6′-O-benzylidene and 4′,6′-O-benzylidene-6-O-TBDMS protected derivatives. Applying a number of regioselective benzylation methods on these gave access to a variety of regioselectively protected derivatives, both mono-ols (2′- and 3-OH), diols (2′,6-, 2′,3-, and 3,6-di-OH), and triols (2′,3,6- and 2′,3′,3-tri-OH). A number of these derivatives were further processed by benzoylation followed by removal or opening of the benzylidene acetal and selective oxidation of the exposed primary alcohol to give heparin building block intermediates comprising a range of possible sulfation patterns.
      Graphical abstract image

      PubDate: 2017-01-13T08:43:52Z
       
  • Structure of O-specific polysaccharide of Oligotropha carboxidovorans OM5
           - A wastewater bacterium
    • Abstract: Publication date: Available online 3 January 2017
      Source:Carbohydrate Research
      Author(s): Iwona Komaniecka, Adam Choma, Katarzyna Zamlynska, Anna Sroka-Bartnicka, Pawel Sowinski
      Oligotropha carboxidovorans strain OM5 (previously known as Pseudomonas carboxydovorans OM5) is a rod-shaped Gram-negative bacterium isolated from wastewater. This bacterium is able to live in aerobic and, facultatively, in autotrophic conditions. For autotrophic growth, the bacteria can utilize carbon monoxide or hydrogen as a source of energy. The O-specific polysaccharide isolated from O. carboxidovorans OM5 lipopolysaccharide was structurally characterized using chemical analyses, 1D and 2D NMR spectroscopy, and MALDI-TOF mass spectrometry techniques. The polysaccharide was found to be a homopolymer built up of 3-O-methyl-α-d-mannose residues linked by (1 → 2)-glycosidic bonds. The degree of polymerization of high-molecular-weight polysaccharide was estimated at approximately 35–40 units. The structure of the homopolymer is depicted below: [→2)-3-OMe-α-d-Manp-(1→]∼35-40
      Graphical abstract image

      PubDate: 2017-01-06T13:50:17Z
       
  • Influence of aglycone structures on N-glycan processing reactions in the
           endoplasmic reticulum
    • Abstract: Publication date: 1 February 2017
      Source:Carbohydrate Research, Volume 439
      Author(s): Kiichiro Totani, Kenta Yamaya, Makoto Hirano, Yukishige Ito
      Glycoprotein N-linked oligosaccharides in the endoplasmic reticulum function as tags to regulate glycoprotein folding, sorting, secretion and degradation. Since the N-glycan structure of a glycoprotein should reflect the folding state, N-glycan processing may be affected by the aglycone state. In this study, we examined the influence of aglycone structures on N-glycan processing using synthetic substrates. We prepared (Glc1)Man9GlcNAc2 linked to hydrophobic BODIPY-dye with a systematic series of different linker lengths. With these compounds, glucose transfer, glucose trimming and mannose trimming reactions of an endoplasmic reticulum fraction were examined. The results showed that substrates with shorter linkers between the N-glycan and hydrophobic patch had higher activities for both the glucose transfer and the mannose trimming reactions. In contrast, the glucose trimming reaction showed lower activity when substrates had shorter linkers. Thus, the reactivity for N-linked oligosaccharide processing of glycoproteins in the endoplasmic reticulum might be tunable by the aglycone structure, e.g., protein portion of glycoproteins.
      Graphical abstract image

      PubDate: 2017-01-06T13:50:17Z
       
  • One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to
           polyhydroxy oxohexanenitrile: A versatile methodology for the facile
           access of azasugar alkaloids
    • Authors: Sandip R. Khobare; Vikas Gajare; E. Vishnuvardhan Reddy; Rajender Datrika; Malavika Banda; Vidavalur Siddaiah; Sharad S. Pachore; Upadhya Timanna; Vilas H. Dahanukar; U.K. Syam Kumar
      Pages: 1 - 6
      Abstract: Publication date: Available online 9 September 2016
      Source:Carbohydrate Research
      Author(s): Sandip R. Khobare, Vikas Gajare, E. Vishnuvardhan Reddy, Rajender Datrika, Malavika Banda, V. Siddaiah, Sharad S. Pachore, Upadhya Timanna, Vilas H. Dahanukar, U.K. Syam Kumar
      A unique oxidative dehydration-oxidation of polyhydroxy-oxime (7) to the corresponding ketonitrile (8) in one pot is reported for the first time in carbohydrate literature. Key ketonitrile intermediate (8) upon palladium hydroxide mediated cascade reaction afforded 1-deoxynojirimycin (DNJ) 1b in moderate diastereoselectivity. The cascade reaction involves the conversion of nitrile to amine, heteroannulation, reduction of the imine and subsequent debenzylation to furnish the azasugars. This oxidative dehydration and reductive heteroannulation methodology is successfully utilized for the total synthesis of 1-deoxynojirimycin (1b), miglitol (2) and miglustat (3).
      Graphical abstract image

      PubDate: 2016-09-18T09:45:20Z
      DOI: 10.1016/j.carres.2016.09.003
      Issue No: Vol. 435 (2016)
       
  • Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands
    • Authors: Benedetta Bertolotti; Beáta Oroszová; Ieva Sutkeviciute; Ladislav Kniežo; Franck Fieschi; Kamil Parkan; Zuzana Lovyová; Martina Kašáková; Jitka Moravcová
      Pages: 7 - 18
      Abstract: Publication date: Available online 9 September 2016
      Source:Carbohydrate Research
      Author(s): Benedetta Bertolotti, Beáta Oroszová, Ieva Sutkeviciute, Ladislav Kniežo, Franck Fieschi, Kamil Parkan, Zuzana Lovyová, Martina Kašáková, Jitka Moravcová
      The discovery of effective ligands for DC-SIGN receptor is one of the most challenging concepts of antiviral drug design due to the importance of this C-type lectin in infection processes. DC-SIGN recognizes mannosylated and fucosylated oligosaccharides but glycosidic linkages are accessible to both chemical and enzymatic degradations. To avoid this problem, the synthesis of stable glycoside mimetics has attracted increasing attention. In this work we establish for the first time mono- and divalent C-glycosides based on d-manno and l-fuco configurations as prospective DC-SIGN ligands. In particular, the l-fucose glycomimetics were more active than the respective d-mannose ones. The highest affinity was assessed for simple 1,4-bis(α-l-fucopyranosyl)butane (SPR: IC50 0.43 mM) that displayed about twice higher activity than natural ligand Lex. Our results make C-glycosides attractive candidates for multivalent presentations.
      Graphical abstract image

      PubDate: 2016-09-10T22:53:33Z
      DOI: 10.1016/j.carres.2016.09.005
      Issue No: Vol. 435 (2016)
       
  • Total synthesis and the anticancer activity of (+)-spisulosine
    • Authors: Milica Fabišíková; Miroslava Martinková; Simona Hirková; Jozef Gonda; Martina Bago Pilátová; Gabriela Gönciová
      Pages: 26 - 36
      Abstract: Publication date: Available online 21 September 2016
      Source:Carbohydrate Research
      Author(s): Milica Fabišíková, Miroslava Martinková, Simona Hirková, Jozef Gonda, Martina Bago Pilátová, Gabriela Gönciová
      The total synthesis of the anticancer agent (+)-spisulosine has been accomplished. The strategy involved a substrate-controlled aza-Claisen rearrangement to establish the erythro-configured amino-alcohol motif followed by deoxygenation to create a methyl side-chain. Subsequent Wittig olefination then permitted the construction of the carbon backbone of the target molecule. To investigate the antiproliferative effect of 1, its biological profile was examined on a panel of 6 human malignant cell lines and demonstrated the significant anticancer activity of 1 on at least five of the evaluated lines with IC50 < 1 μM (MCF-7, HTC-116, Caco-2, Jurkat and HeLa).
      Graphical abstract image

      PubDate: 2016-09-23T17:38:08Z
      DOI: 10.1016/j.carres.2016.09.010
      Issue No: Vol. 435 (2016)
       
  • Function-spacer-lipid constructs of Lewis and chimeric Lewis/ABH glycans.
           Synthesis and use in serological studies
    • Authors: Ivan M. Ryzhov; Elena Yu. Korchagina; Alexander B. Tuzikov; Inna S. Popova; Tatiana V. Tyrtysh; Galina V. Pazynina; Stephen M. Henry; Nicolai V. Bovin
      Pages: 83 - 96
      Abstract: Publication date: Available online 28 September 2016
      Source:Carbohydrate Research
      Author(s): Ivan M. Ryzhov, Elena Yu Korchagina, Alexander B. Tuzikov, Inna S. Popova, Tatiana V. Tyrtysh, Galina V. Pazynina, Stephen M. Henry, Nicolai V. Bovin
      Seven lipophilic constructs containing Lewis (Lea, Leb, Ley) or chimeric Lewis/ABH (ALeb, BLeb, ALey, BLey) glycans were obtained starting from corresponding oligosaccharides in form of 3-aminopropyl glycosides. ALeb and BLeb pentasaccharides were synthesized via [3 + 1] blockwise approach. The constructs (neoglycolipids, or FSLs) were inserted in erythrocyte membrane, and obtained “kodecytes” were used to map the immunochemical specificity of historical and contemporary monoclonal and polyclonal blood group system Lewis reagents.
      Graphical abstract image

      PubDate: 2016-10-04T00:05:36Z
      DOI: 10.1016/j.carres.2016.09.016
      Issue No: Vol. 435 (2016)
       
  • Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of
           1,4-dideoxy-1,4-imino-D-galactitol and 1,4-dideoxy-1,4-imino-D-glucitol
    • Authors: Giuliana Righi; Emanuela Mandic'; Carla Sappino; Ergys Dema; Paolo Bovicelli
      Pages: 100 - 105
      Abstract: Publication date: Available online 3 October 2016
      Source:Carbohydrate Research
      Author(s): Giuliana Righi, Emanuela Mandic', Carla Sappino, Ergys Dema, Paolo Bovicelli
      Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-D-galactitol and its diastereoisomer 1,4-dideoxy-1,4-imino-D-glucitol is described, starting from a common optically active precursor. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereoselective nucleophilic openings of the corresponding chiral vinyl epoxide.
      Graphical abstract image

      PubDate: 2016-10-04T00:05:36Z
      DOI: 10.1016/j.carres.2016.09.018
      Issue No: Vol. 435 (2016)
       
  • Getting a grip on glycans: A current overview of the metabolic
           oligosaccharide engineering toolbox
    • Authors: Tjerk J. Sminia; Han Zuilhof; Tom Wennekes
      Pages: 121 - 141
      Abstract: Publication date: 29 November 2016
      Source:Carbohydrate Research, Volume 435
      Author(s): Tjerk J. Sminia, Han Zuilhof, Tom Wennekes
      This review discusses the advances in metabolic oligosaccharide engineering (MOE) from 2010 to 2016 with a focus on the structure, preparation, and reactivity of its chemical probes. A brief historical overview of MOE is followed by a comprehensive overview of the chemical probes currently available in the MOE molecular toolbox and the bioconjugation techniques they enable. The final part of the review focusses on the synthesis of a selection of probes and finishes with an outlook on recent and potential upcoming advances in the field of MOE.
      Graphical abstract image

      PubDate: 2016-10-16T22:43:34Z
      DOI: 10.1016/j.carres.2016.09.007
      Issue No: Vol. 435 (2016)
       
  • Structure of the O-specific polysaccharide from the lipopolysaccharide of
           Aeromonas hydrophila strain K691 containing
           4-acetamido-4,6-dideoxy-D-glucose
    • Abstract: Publication date: Available online 23 December 2016
      Source:Carbohydrate Research
      Author(s): Katarzyna Pakiet, Anna Turska-Szewczuk, Magdalena A. Karas, Agnieszka Pekala, Hubert Pietras
      The O-specific polysaccharide (OPS) was isolated from the lipopolysaccharide of Aeromonas hydrophila strain K691 and studied by chemical methods and 1H and 13C NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, NOESY, 1H-detected heteronuclear 1H,13C HSQC, and HMBC experiments. It was found that the O-specific polysaccharide was built up of pentasaccharide repeating units composed of β-GlcpNAc, 2-O-acetylated α-Rhap, and β-Quip4NAc residues. The following structure of the OPS was established: →3)-α-l-Rha2OAc-(1→3)-β-d-GlcNAc-(1→3)-α-l-Rha2OAc-(1→3)-β-d-GlcNAc-(1→2)-β-d-Qui4NAc-(1→
      Graphical abstract image

      PubDate: 2016-12-27T06:46:27Z
       
  • Graphical contents list
    • Abstract: Publication date: 13 January 2017
      Source:Carbohydrate Research, Volume 438


      PubDate: 2016-12-27T06:46:27Z
       
  • New investigators in glycoscience
    • Abstract: Publication date: 13 January 2017
      Source:Carbohydrate Research, Volume 438
      Author(s): Rob Field


      PubDate: 2016-12-27T06:46:27Z
       
  • Removal of some common glycosylation by-products during reaction work-up
    • Abstract: Publication date: Available online 24 December 2016
      Source:Carbohydrate Research
      Author(s): Mads Heuckendorff, Henrik H. Jensen
      With the aim of improving the general glycosylation protocol to facilitate easy product isolation it was shown that amide by-products from glycosylation with trichloroacetimidate and N-phenyl trifluoroacetimidate donors could be removed during reaction work-up by washing with a basic aqueous solution. Excess glycosyl acceptor or lactol originating from glycosyl donor hydrolysis could equally be removed from the reaction mixture by derivatization with a basic tag and washing with an acidic solution during reaction work-up.
      Graphical abstract image

      PubDate: 2016-12-27T06:46:27Z
       
  • Photoswitchable carbohydrate-based fluorosurfactants as tuneable ice
           recrystallization inhibitors
    • Abstract: Publication date: Available online 14 December 2016
      Source:Carbohydrate Research
      Author(s): Madeleine K. Adam, Yingxue Hu, Jessica S. Poisson, Matthew J. Pottage, Robert N. Ben, Brendan L. Wilkinson
      Cryopreservation is an important biomedical technique employed for the storage and preservation of biological tissues and cells. The limited effectiveness and significant toxicity of conventionally-used cryoprotectants, such as DMSO, have prompted efforts toward the rational design of less toxic alternatives, including carbohydrate surfactants. In this paper, we report the modular synthesis and ice recrystallization inhibition (IRI) activity of a library of variably substituted, carbohydrate-based fluorosurfactants. Carbohydrate-based fluorosurfactants possessed a variable mono- or disaccharide head group appended to a hydrophobic fluoroalkyl-substituted azobenzene tail group. Light-addressable fluorosurfactants displayed weak-to-moderate IRI activity that could be tuned through selection of carbohydrate head group, position of the trifluoroalkyl group on the azobenzene ring, and isomeric state of the azobenzene tail fragment.
      Graphical abstract image

      PubDate: 2016-12-20T09:41:49Z
       
  • Evaluation of carbohydrate-cysteamine thiazolidines as pro-drugs for the
           treatment of cystinosis
    • Abstract: Publication date: Available online 18 December 2016
      Source:Carbohydrate Research
      Author(s): Yasaman Ramazani, Elena N. Levtchenko, Lambertus Van Den Heuvel, Ann Van Schepdael, Prasanta Paul, Ekaterina A. Ivanova, Anna Pastore, Trina M. Hartman, Neil P.J. Price
      Cystinosis is a genetic disorder caused by malfunction of cystinosin and is characterized by accumulation of cystine. Cysteamine, the medication used in cystinosis, causes halitosis resulting in poor patient compliance. Halitosis is mainly caused by the formation of dimethylsulfide as the final product in the cysteamine metabolism pathway. We have synthesized carbohydrate-cysteamine thiazolidines, and hypothesized that the hydrolytic breakdown of cysteamine-thiazolidines can result in free cysteamine being released in target organs. To examine our hypothesis, we tested these analogs in vitro in patient-derived fibroblasts. Cystinotic fibroblasts were treated with different concentrations of arabinose-cysteamine, glucose-cysteamine and maltose-cysteamine. We demonstrated that the analogs break down into cysteamine extracellularly and might therefore not be fully taken up by the cells under the form of the pro-drug. Potential modifications of the analogs that enable their intracellular rather than extracellular breakdown, is necessary to pursue the potential of these analogs as pro-drugs.
      Graphical abstract image

      PubDate: 2016-12-20T09:41:49Z
       
  • Investigating the relationship between temperature, conformation and
           calcium binding in heparin model oligosaccharides
    • Abstract: Publication date: Available online 9 December 2016
      Source:Carbohydrate Research
      Author(s): Ashley Hughes, Maria Meneghetti, Teng-Yi Huang, Shang-Cheng Huang, Stefano Elli, Marco Guerrini, Timothy Rudd, Marcelo Lima, Edwin Yates
      Glycosaminoglycans such as heparan sulfate (HS) are major components of the cell surface and extracellular matrix (ECM) of all multicellular animals, connecting cells to each other as well as to their environment. The ECM must, therefore, both sense and accommodate changes to external conditions. Heparin, a model compound for HS, responds to increased temperatures, involving changes in the populations of conformational states with implications for the binding of HS to proteins, cations and, potentially, for its activity. A fully 13C and 15N labelled model octasasccharide; D-GlcNS6S α(1-4) L-IdoA2S [α(1-4) D-GlcNS6S α(1-4) L-IdoA2S]2 α(1-4) D-GlcNS6S α(1-4) L-IdoA1,6an, was studied by 1H, 13C and 15N NMR, revealing complex changes in chemical shifts and conformation, over temperatures (280–305 K), comfortably within the range relevant to terrestrial biology. These complex conformational changes indicated an interaction between the carboxylate group of L-iduronate and D-glucosamine residues that was susceptible to temperature changes in this range, while the well-documented hydrogen bond between the N-sulfamido group of glucosamine and the hydroxyl group at position-3 of iduronate remained intact. Unexpectedly, despite the presence of similar thermally-induced conformational changes in a heparin octasaccharide fraction in the sodium ion form, its subsequent binding to calcium ions and their resulting conformation was stringently maintained, as judged by comparisons of 1H NMR chemical shifts.
      Graphical abstract image

      PubDate: 2016-12-13T09:32:46Z
       
  • Graphical contents list
    • Abstract: Publication date: 2 January 2017
      Source:Carbohydrate Research, Volume 437


      PubDate: 2016-12-13T09:32:46Z
       
  • Synthesis and NMR analysis of model compounds related to fucosylated
           chondroitin sulfates: GalNAc and Fuc(1 → 6)GalNAc derivatives
    • Abstract: Publication date: 13 January 2017
      Source:Carbohydrate Research, Volume 438
      Author(s): Dmitry Z. Vinnitskiy, Nadezhda E. Ustyuzhanina, Andrey S. Dmitrenok, Alexander S. Shashkov, Nikolay E. Nifantiev
      Unsubstituted and 6-O-α-L-fucosylated propyl 2-acetamido-2-deoxy-β-D-galactopyranosides and their selectively O-sulfated (both in GalNAc and Fuc units) derivatives were synthesized as model compounds representing the fragments of fucosylated chondroitin sulfates (FCS) from sea cucumbers. Per-O-acetylated 2-deoxy-2-N-phthalimido-D-glucopyranose was used as a key precursor for the preparation of all 2-acetamido-2-deoxy-D-galactopyranoside containing products. Attempts at 6-O-glycosylation of propyl 3-O-benzoyl-2-deoxy-2-N-phthalimido-D-galactoside by 2-O-benzyl-3,4-di-O-chloracetyl-L-fucosyl trichloracetimidate in the presence of TMSOTf gave a 1:1 mixture of the corresponding α- and β-isomeric disaccharides, while the use of structurally related fucosyl bromide donor with promotion by Bu4NBr led to the formation of desired α-isomeric disaccharide exclusively. Selective removal of orthogonal O-protections permitted subsequent O-sulfation both at the GalNAc and Fuc units. Further removal of blocking groups yielded the target products which were systematically studied by 1H and 13C NMR spectroscopy in order to determine the spectral effects of O-sulfation and α-L-fucosylation needed for the development of computer assisted structural analysis of natural FCS.
      Graphical abstract image

      PubDate: 2016-12-13T09:32:46Z
       
  • Fluorescent mannosides serve as acceptor substrates for
           glycosyltransferase and sugar-1-phosphate transferase activities in
           Euglena gracilis membranes
    • Abstract: Publication date: Available online 30 November 2016
      Source:Carbohydrate Research
      Author(s): Irina M. Ivanova, Sergey A. Nepogodiev, Gerhard Saalbach, Ellis C. O'Neill, Michael D. Urbaniak, Michael A.J. Ferguson, Sudagar S. Gurcha, Gurdyal S. Besra, Robert A. Field
      Synthetic hexynyl α-D-mannopyranoside and its α-1,6-linked disaccharide counterpart were fluorescently labelled through CuAAC click chemistry with 3-azido-7-hydroxycoumarin. The resulting triazolyl-coumarin adducts, which were amenable to analysis by TLC, HPLC and mass spectrometry, proved to be acceptor substrates for α-1,6-ManT activities in mycobacterial membranes, as well as α- and β-GalT activities in trypanosomal membranes, benchmarking the potential of the fluorescent acceptor approach against earlier radiochemical assays. Following on to explore the glycobiology of the benign protozoan alga Euglena gracilis, α-1,3- and α-1,2-ManT activities were detected in membrane preparations, along with GlcT, Glc-P-T and GlcNAc-P-T activities. These studies serve to demonstrate the potential of readily accessible fluorescent glycans as substrates for exploring carbohydrate active enzymes.
      Graphical abstract image

      PubDate: 2016-12-06T09:25:11Z
       
  • Synthesis of aza-crown analogues and macrocyclic bis-lactams with sucrose
           scaffold
    • Abstract: Publication date: Available online 5 December 2016
      Source:Carbohydrate Research
      Author(s): Michał Kowalski, Sławomir Jarosz
      2,3,3′,4,4′-Penta-O-benzylsucrose was converted into the corresponding diaminoalcohol which was used as a key building block in the synthesis of the analogues of aza-crown ethers and bis-lactams.
      Graphical abstract image

      PubDate: 2016-12-06T09:25:11Z
       
  • Corrigendum to “Structures and gene clusters of the closely related
           O-antigens of Escherichia coli O46 and O134, both containing
           d-glucuronoyl-d-allothreonine” [Carbohydr. Res. 409 (2015) 20–24]
    • Abstract: Publication date: 21 December 2016
      Source:Carbohydrate Research, Volume 436
      Author(s): Andrei V. Perepelov, Quan Wang, Andrei V. Filatov, Xianghong Xia, Alexander S. Shashkov, Andrej Weintraub, Göran Widmalm, Lei Wang, Yuriy A. Knirel


      PubDate: 2016-12-06T09:25:11Z
       
  • Enzymatic synthesis of human blood group P1 pentasaccharide antigen
    • Abstract: Publication date: Available online 5 December 2016
      Source:Carbohydrate Research
      Author(s): Dawa Tsering, Congcong Chen, Jinfeng Ye, Zhipeng Han, Bai-qian Jing, Xian-wei Liu, Xi Chen, Fengshan Wang, Peixue Ling, Hongzhi Cao
      The enzymatic synthesis of biologically important and structurally unique human P1PK blood group type P1 pentasaccharide antigen is described. This synthesis features a three-step sequential one-pot multienzyme (OPME) glycosylation for the stepwise enzymatic chain elongation of readily available lactoside acceptor with cheap and commercially available galactose and N-acetylglucosamine as donor precursors. This enzymatic synthesis provides an operationally simple approach to access P1 pentasaccharide and its structurally related Gb3 and P1 trisaccharide epitopes.
      Graphical abstract image

      PubDate: 2016-12-06T09:25:11Z
       
  • Graphical contents list
    • Abstract: Publication date: 21 December 2016
      Source:Carbohydrate Research, Volume 436


      PubDate: 2016-12-06T09:25:11Z
       
  • One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals:
           Application in the syntheses of chromanone 3-C-glycosides
    • Abstract: Publication date: Available online 30 November 2016
      Source:Carbohydrate Research
      Author(s): Ashutosh K. Dash, Tatina Madhubabu, Syed Khalid Yousuf, Sushil Raina, Debaraj Mukherjee
      One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.
      Graphical abstract image

      PubDate: 2016-12-06T09:25:11Z
       
  • Carbohydrate-based aza-macrocycles by Richman-Atkins cyclization of
           glucopyranose precursors
    • Abstract: Publication date: Available online 29 November 2016
      Source:Carbohydrate Research
      Author(s): Andreas Rathjens, Joachim Thiem
      2, 3-Di-ω-halo- as well as 2, 3-di-ω-toluenesulfonamide-alkylated glucopyranoside derivatives were prepared. Their condensation with α,ω-bis-toluenesulfonamide components under varying Richman-Atkins conditions with alkali carbonate in DMF led to carbohydrate-linked aza-macrocycles displaying 14-, 17-, 18-, 21-, 24-, and 25-membered ring structures. Isomeric aza-macrocylic coronands of 20- as well as 30-membered ring size containing two saccharides could be obtained employing Richman-Atkins condensations of two functionalized sugar building units.
      Graphical abstract image

      PubDate: 2016-11-30T04:30:11Z
       
  • AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl
           donors at room temperature
    • Abstract: Publication date: Available online 23 November 2016
      Source:Carbohydrate Research
      Author(s): Ashokkumar Palanivel, Ande Chennaiah, Sateesh Dubbu, Asadulla Mallick, Yashwant D. Vankar
      Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20–60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.
      Graphical abstract image

      PubDate: 2016-11-24T11:38:09Z
       
  • Characterization of the LM5 pectic galactan epitope with synthetic
           analogues of β-1,4-d-galactotetraose
    • Abstract: Publication date: 21 December 2016
      Source:Carbohydrate Research, Volume 436
      Author(s): Mathias C.F. Andersen, Irene Boos, Susan E. Marcus, Stjepan K. Kračun, Maja Gro Rydahl, William G.T. Willats, J. Paul Knox, Mads H. Clausen
      Plant cell wall glycans are important polymers that are crucial to plant development and serve as an important source of sustainable biomass. The study of polysaccharides in the plant cell wall relies heavily on monoclonal antibodies (mAbs) for localization and visualization of glycans, using e.g. immunofluorescent microscopy. Here, we describe the detailed epitope mapping of the mAb LM5 that is shown to bind to a minimum of three sugar residues at the non-reducing end of linear beta-1,4-linked galactan. The study uses de novo synthetic analogues of galactans combined with carbohydrate microarray and competitive inhibition ELISA for analysis of antibody-carbohydrate interactions.
      Graphical abstract image

      PubDate: 2016-11-17T01:35:12Z
       
  • Graphical contents list
    • Abstract: Publication date: 29 November 2016
      Source:Carbohydrate Research, Volume 435


      PubDate: 2016-11-17T01:35:12Z
       
  • Scalable preparation, characterization, and application of alkali-treated
           starch as a new organic base catalyst
    • Abstract: Publication date: Available online 16 November 2016
      Source:Carbohydrate Research
      Author(s): Fatemeh Tamaddon, MohammadTaghi KazemiVarnamkhasti
      Preparation, characterization, and application of alkali starch (AS) given by dry co-grinding of starch and alkali is described in this work. Grinding using a mortar (agate) and pestle or, more conveniently, a ball mill has been found to be satisfactory for the preparation of the AS. The AS products were characterized by scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) and x-ray fluorescence (XRF) analyses. The base capacities of ASs were 4.25–4.45 mmol/g, respectively. AS is a low cost and easy to handle base catalyst that showed promising catalytic performance in the synthesis of a dihydroquinazoline-based antibacterial drug that involves tandem hydration or decarboxylative amidation, imination, and Aza-Michael reactions.
      Graphical abstract image

      PubDate: 2016-11-17T01:35:12Z
       
  • Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues
    • Abstract: Publication date: Available online 14 November 2016
      Source:Carbohydrate Research
      Author(s): Duc Thinh Khong, Zaher M.A. Judeh
      A short synthesis of phenylethyl glycosides grayanoside-A 1, 2 and analogues 3–4 in high 43–65% overall yields is described. The main synthetic step involved regioselective O-6 acylation of unprotected 2-phenylethyl-β-D-glucoside 7 with cinnamoyl chlorides 8a-d using Me2SnCl2 as catalyst. The acylation at O-6 is regioselective regardless of the type of cinnamoyl chloride used. Protection/deprotection steps of the glucoside core were not necessary. The synthetic route is generally applicable for the synthesis of phenylpropanoid glycoside class of compounds acylated at O-6.
      Graphical abstract image

      PubDate: 2016-11-17T01:35:12Z
       
  • Tri- and tetravalent mannoclusters cross-link and aggregate BC2L-A lectin
           from Burkholderia cenocepacia
    • Abstract: Publication date: Available online 14 November 2016
      Source:Carbohydrate Research
      Author(s): Magdolna Csávás, Lenka Malinovská, Perret Florent, Milán Gyurkó, Zita Tünde Illyés, Michaela Wimmerová, Anikó Borbás
      The opportunistic Gram-negative bacterium Burkholderia cenocepacia causes lethal infections in cystic fibrosis patients. Multivalent mannoside derivatives were prepared as potential inhibitors of lectin BC2L-A, one of the virulence factors deployed by B. cenocepacia in the infection process. An (α1→2)-thio-linked mannobioside mimic bearing an azide functionalized aglycon was conjugated to different multivalent scaffolds such as propargylated calix[4]arenes, methyl gallate and pentaerythritol by azide-alkyne 1,3-dipolar cycloaddition. The interaction between the glycoclusters and the mannose binding BC2L-A lectin from B. cenocepacia was examined by isothermal microcalorimetry, surface plasmon resonance, inhibition of yeast agglutination and analytical ultracentrifugation.
      Graphical abstract image

      PubDate: 2016-11-17T01:35:12Z
       
  • Bimodal concentration-dependent reactivity pattern of a glycosyl donor: Is
           the solution structure involved?
    • Abstract: Publication date: Available online 12 November 2016
      Source:Carbohydrate Research
      Author(s): Leonid O. Kononov, Ksenia G. Fedina, Anna V. Orlova, Nikolay N. Kondakov, Polina I. Abronina, Nikita M. Podvalnyy, Alexander O. Chizhov
      Changes in concentration (0.001–0.1 M) of an arabinofuranosyl donor (1) have been shown to modulate the temperature T at which activation of 1 occurs (from −23 °C to +7 °C), the reaction time (from 1.5 h to 3 days) and the yield of the disaccharide formed (from 14% to 82%). At concentrations exceeding 0.01 M, these parameters, as well as the specific optical rotation of the solution of 1, virtually do not depend on concentration suggesting formation of reacting species (supramers) of glycosyl donor with similar structures, hence reactivities, but considerably different from those formed in more dilute solutions. The found critical concentration (0.01 M) separates two concentration ranges of reaction solutions corresponding to two types of solution structure that are featured by the presence of fundamentally different supramers of glycosyl donor, which have distinct chemical properties. These results allow a fresh look at the problems of reactivity of chemical compounds and selectivity of the reactions in which they participate.
      Graphical abstract image

      PubDate: 2016-11-17T01:35:12Z
       
  • Infant food applications of complex carbohydrates: Structure, synthesis,
           and function
    • Abstract: Publication date: Available online 11 November 2016
      Source:Carbohydrate Research
      Author(s): Dorothy L. Ackerman, Kelly M. Craft, Steven D. Townsend
      Professional health bodies such as the World Health Organization (WHO), the American Academy of Pediatrics (AAP), and the U.S. Department of Health and Human Services (HHS) recommend breast milk as the sole source of food during the first year of life. This position recognizes human milk as being uniquely suited for infant nutrition. Nonetheless, most neonates in the West are fed alternatives by 6 months of age. Although inferior to human milk in most aspects, infant formulas are able to promote effective growth and development. However, while breast-fed infants feature a microbiota dominated by bifidobacteria, the bacterial flora of formula-fed infants is usually heterogeneous with comparatively lower levels of bifidobacteria. Thus, the objective of any infant food manufacturer is to prepare a product that results in a formula-fed infant developing a breast-fed infant-like microbiota. The goal of this focused review is to discuss the structure, synthesis, and function of carbohydrate additives that play a role in governing the composition of the infant microbiome and have other health benefits.
      Graphical abstract image

      PubDate: 2016-11-17T01:35:12Z
       
  • Synthesis of 3-aminopropyl glycoside of branched
           β-(1 → 3)-d-glucooctaoside
    • Abstract: Publication date: Available online 9 November 2016
      Source:Carbohydrate Research
      Author(s): Dmitry V. Yashunsky, Yury E. Tsvetkov, Nikolay E. Nifantiev
      The synthesis was described of branched glucooctaoside bearing the β-(1 → 3)-glucotrioside side chain at O-6 of the second (from the reducing end) monosaccharide unit of the linear β-(1 → 3)-glucopentaoside core.
      Graphical abstract image

      PubDate: 2016-11-11T01:27:25Z
       
  • Dihydroresveratrol cellobioside and xylobioside as effective melanogenesis
           activators
    • Abstract: Publication date: Available online 9 November 2016
      Source:Carbohydrate Research
      Author(s): Chisato Oode, Wataru Shimada, Mariko Yokota, Yoichi Yamada, Ken-ichi Nihei
      Dihydroresveratrol cellobioside and xylobioside, whose structure were designed based on that of naturally occurring melanogenesis-controlled agent dihydroresveratrol glucoside, were synthesized via Schmidt glycosylation as the key step. Both analogues stimulated melanogenesis with efficacies comparable to that of 8-methoxypsoralen, a well-known melanogenesis activator. This suggests that diglycosyl modification of the 4-OH on the dihydroresveratrol skeleton leads to the activation of melanogenesis, both with and without hydroxymethyl groups in the sugar moieties.
      Graphical abstract image

      PubDate: 2016-11-11T01:27:25Z
       
  • Non-enzymatic reaction of glycosyl oxazoline with peptides
    • Abstract: Publication date: Available online 5 November 2016
      Source:Carbohydrate Research
      Author(s): Ning Wang, Akira Seko, Shusaku Daikoku, Osamu Kanie, Yoichi Takeda, Yukishige Ito
      Recently, a number of chemoenzymatic strategies have been explored for achieving preparation of homogeneous glycopeptides and glycoproteins, especially by using endoglycanases and glycosyl oxazolines. However, concomitant occurrence of non-enzymatic reactions has been reported, but no further characterization of the byproducts was conducted. In this work, we made an attempt to identify the side product by using model substrates. Analysis of the product allowed us to propose that the oxazoline ring was attacked by the amino group of lysine, leading to the formation of disubstituted acetamidine.
      Graphical abstract image

      PubDate: 2016-11-11T01:27:25Z
       
  • Binding pattern of intermediate UDP-4-keto-xylose to human UDP-xylose
           synthase: Synthesis and STD NMR of model keto-saccharides
    • Abstract: Publication date: Available online 5 November 2016
      Source:Carbohydrate Research
      Author(s): Claudia Puchner, Thomas Eixelsberger, Bernd Nidetzy, Lothar Brecker
      Human UDP-xylose synthase (hUXS1) exclusively converts UDP-glucuronic acid to UDP-xylose via intermediate UDP-4-keto-xylose (UDP-Xyl-4O). Synthesis of model compounds like methyl-4-keto-xylose (Me-Xyl-4O) is reported to investigate the binding pattern thereof to hUXS1. Hence, selective oxidation of the desired hydroxyl function required employment of protecting group chemistry. Solution behavior of synthesized keto-saccharides was studied without enzyme via 1H and 13C NMR spectroscopy with respect to existent forms in deuterated potassium phosphate buffer. Keto-enol tautomerism was observed for all investigated keto-saccharides, while gem-diol hydrate forms were only observed for 4-keto-xylose derivatives. Saturation transfer difference (STD) NMR was used to study binding of synthesized keto-gylcosides to wild type hUXS1. Resulting epitope maps were correlated to earlier published molecular modeling studies of UDP-Xyl-4O. STD NMR results of Me-Xyl-4O are in good agreement with simulations of the intermediate UDP-Xyl-4O indicating a strong interaction of proton H3 with the enzyme, potentially caused by active site residue Ala79. In contrast, pyranoside binding pattern studies of methyl uronic acids showed some differences compared to previously published STD NMR results of UDP-glycosides. In general, obtained results can contribute to a better understanding in binding of UDP-glycosides to other UXS enzyme family members, which have high structural similarities in the active site.
      Graphical abstract image

      PubDate: 2016-11-11T01:27:25Z
       
  • Preparation of the tri-arabino di-mycolate fragment of mycobacterial
           arabinogalactan from defined synthetic mycolic acids
    • Abstract: Publication date: Available online 10 November 2016
      Source:Carbohydrate Research
      Author(s): Mohsin O. Mohammed, Juma'a R. Al Dulayymi, Mark S. Baird
      An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.
      Graphical abstract image

      PubDate: 2016-11-11T01:27:25Z
       
  • Structure elucidation and analysis of biosynthesis genes of the O-antigen
           of Escherichia coli O131 containing N-acetylneuraminic acid
    • Abstract: Publication date: Available online 4 November 2016
      Source:Carbohydrate Research
      Author(s): Andrei V. Perepelov, Xi Guo, Sof'ya N. Senchenkova, Alexander S. Shashkov, Bin Liu, Yuriy A. Knirel
      The O-polysaccharide (O-antigen) of Escherichia coli O131 was studied by sugar analysis along with 1D and 2D 1H and 13C NMR spectroscopy. The following structure of the linear tetrasaccharide repeating unit of the polysaccharide was established: →8)-α-Neup5Ac-(2 → 6)-β-D-Galp-(1 → 6)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1→ The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in agreement with the E. coli O131-antigen structure.
      Graphical abstract image

      PubDate: 2016-11-04T22:05:40Z
       
  • Ring distortion in pyranosides caused by per-O-sulfation
    • Abstract: Publication date: Available online 29 October 2016
      Source:Carbohydrate Research
      Author(s): Alexey G. Gerbst, Vadim B. Krylov, Dmitry A. Argunov, Arsenii S. Solovev, Andrey S. Dmitrenok, Alexander S. Shashkov, Nikolay E. Nifantiev
      Distortion of the ring conformation in β-gluco- and β-xylopyranosides upon their per-O-sulfation was observed. In the case of glucose, a conformation intermediate between 3,OB and 3S1 was found, while complete 4C1→1C4 inversion was detected in xylopyranoside. The conformational changes were evidenced experimentally by measuring intra-ring 1H–1H coupling constants and nuclear Overhauser effect (NOE) and were additionally confirmed by ab initio calculations.
      Graphical abstract image

      PubDate: 2016-10-29T21:50:14Z
       
  • Glycerol carbonate in Ferrier reaction: Access to new enantiopure building
           blocks to develop glycoglycerolipid analogues
    • Abstract: Publication date: Available online 26 October 2016
      Source:Carbohydrate Research
      Author(s): Pollyanna Leite Ferreira da Costa, Valentina Nascimento e Melo, Bruna Martins Guimarães, Marie Schuler, Vanessa Pimenta, Patrick Rollin, Arnaud Tatibouët, Ronaldo Nascimento de Oliveira
      Glycerol carbonate and tri-O-acetyl-D-glucal were used for the synthesis of glycero-functionalized carbohydrates. Ferrier reaction between the two partners afforded the O-glucoside in 84% yield. Spontaneous crystallization yielded 28% of a pure diastereoisomer with the S configuration as determined by X-ray crystallography. Then, the azido-glycerosugar was prepared in two steps: ring opening of the cyclic carbonate with sodium azide and per-acetylation with an excellent yield of 94%. A library of glycoconjugates were prepared using a 1,3-dipolar cycloaddition in yields ranging from 64 to 99%.
      Graphical abstract image

      PubDate: 2016-10-29T21:50:14Z
       
  • From secondary alcohols to tertiary fluoro substituents: A simple route to
           hydroxymethyl branched sugars with a fluorine substituent at the branching
           point
    • Abstract: Publication date: Available online 29 October 2016
      Source:Carbohydrate Research
      Author(s): Michael Schalli, Martin Thonhofer, Andreas Wolfsgruber, Hansjörg Weber, Roland Fischer, Robert Saf, Arnold E. Stütz
      From a secondary hydroxyl group, by the simple sequence of oxidation, Wittig reaction of the obtained ulose with methoxymethylene triphenyl phosphorane, exposure of the resulting exocyclic enol ether to Selectfluor and subsequent reduction of the α-fluoro aldehyde thus obtained, tertiary fluoro substituents can be introduced into carbohydrate and carbohydrate-related scaffolds at a branching point now bearing a new hydroxymethyl group.
      Graphical abstract image

      PubDate: 2016-10-29T21:50:14Z
       
  • Diastereoselective synthesis of furanose and pyranose substituted glycine
           and alanine derivatives via proline-catalyzed asymmetric α-amination of
           aldehydes
    • Authors: Ramu Petakamsetty; Anas Ansari; Ramesh Ramapanicker
      Abstract: Publication date: Available online 21 September 2016
      Source:Carbohydrate Research
      Author(s): Ramu Petakamsetty, Anas Ansari, Ramesh Ramapanicker
      A concise organocatalytic route toward the synthesis of furanose and pyranose substituted glycine and alanine derivatives is reported. These compounds are core structural units of some of the naturally available antibiotics and antifungal agents. Proline-catalyzed asymmetric α-amination of aldehydes derived from sugars is used as the key reaction to synthesize twelve sugar amino acid derivatives. The asymmetric transformations proceeded in good yields and with good to excellent diastereoselectivity. The application of the synthesized amino acids is demonstrated by synthesizing a tripeptide containing one of them.
      Graphical abstract image

      PubDate: 2016-09-23T17:38:08Z
      DOI: 10.1016/j.carres.2016.09.011
       
 
 
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