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  Subjects -> CHEMISTRY (Total: 848 journals)
    - ANALYTICAL CHEMISTRY (47 journals)
    - 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: 26)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 15)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 23)
ACS Macro Letters     Full-text available via subscription   (Followers: 20)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 33)
ACS Nano     Full-text available via subscription   (Followers: 167)
ACS Photonics     Full-text available via subscription   (Followers: 6)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 16)
Acta Chemica Iasi     Open Access  
Acta Chimica Sinica     Full-text available via subscription  
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  
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: 43)
Advanced Science Focus     Free   (Followers: 3)
Advances in Chemical Engineering and Science     Open Access   (Followers: 50)
Advances in Chemical Science     Open Access   (Followers: 11)
Advances in Chemistry     Open Access   (Followers: 9)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 14)
Advances in Drug Research     Full-text available via subscription   (Followers: 21)
Advances in Enzyme Research     Open Access   (Followers: 4)
Advances in Fluorine Science     Full-text available via subscription   (Followers: 8)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 12)
Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 8)
Advances in Materials Physics and Chemistry     Open Access   (Followers: 15)
Advances in Nanoparticles     Open Access   (Followers: 12)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 14)
Advances in Polymer Science     Hybrid Journal   (Followers: 37)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 13)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 13)
Advances in Quantum Chemistry     Full-text available via subscription   (Followers: 5)
Advances in Science and Technology     Full-text available via subscription   (Followers: 5)
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: 61)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 13)
American Journal of Chemistry     Open Access   (Followers: 23)
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: 41)
Angewandte Chemie     Hybrid Journal   (Followers: 120)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 168)
Annales UMCS, Chemia     Open Access   (Followers: 1)
Annals of Clinical Chemistry and Laboratory Medicine     Open Access   (Followers: 1)
Annual Reports in Computational Chemistry     Full-text available via subscription   (Followers: 2)
Annual Reports Section A (Inorganic Chemistry)     Full-text available via subscription   (Followers: 3)
Annual Reports Section B (Organic Chemistry)     Full-text available via subscription   (Followers: 7)
Annual Review of Chemical and Biomolecular Engineering     Full-text available via subscription   (Followers: 9)
Annual Review of Food Science and Technology     Full-text available via subscription   (Followers: 13)
Anti-Infective Agents     Hybrid Journal   (Followers: 3)
Antiviral Chemistry and Chemotherapy     Full-text available via subscription  
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 5)
Applied Spectroscopy     Full-text available via subscription   (Followers: 23)
Applied Surface Science     Hybrid Journal   (Followers: 22)
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: 4)
Autophagy     Hybrid Journal   (Followers: 2)
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 7)
Biochemistry     Full-text available via subscription   (Followers: 223)
Biochemistry Insights     Open Access   (Followers: 4)
Biochemistry Research International     Open Access   (Followers: 5)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 8)
Bioinspired Materials     Open Access   (Followers: 2)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 1)
Biointerphases     Open Access   (Followers: 1)
Biology, Medicine, & Natural Product Chemistry     Open Access  
Biomacromolecules     Full-text available via subscription   (Followers: 17)
Biomass Conversion and Biorefinery     Partially Free   (Followers: 11)
Biomedical Chromatography     Hybrid Journal   (Followers: 7)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 2)
BioNanoScience     Partially Free   (Followers: 4)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 93)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 84)
Bioorganic Chemistry     Hybrid Journal   (Followers: 9)
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: 25)
Bulletin of the Korean Chemical Society     Hybrid Journal  
C - Journal of Carbon Research     Open Access   (Followers: 2)
Canadian Association of Radiologists Journal     Full-text available via subscription   (Followers: 2)
Canadian Journal of Chemistry     Full-text available via subscription   (Followers: 6)
Canadian Mineralogist     Full-text available via subscription   (Followers: 3)
Carbohydrate Research     Hybrid Journal   (Followers: 27)
Carbon     Hybrid Journal   (Followers: 65)
Catalysis for Sustainable Energy     Open Access   (Followers: 5)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 7)
Catalysis Science and Technology     Free   (Followers: 5)
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  
ChemCatChem     Hybrid Journal   (Followers: 6)
Chemical and Engineering News     Free   (Followers: 11)
Chemical Bulletin of Kazakh National University     Open Access  
Chemical Communications     Full-text available via subscription   (Followers: 63)
Chemical Engineering Research and Design     Hybrid Journal   (Followers: 21)
Chemical Research in Chinese Universities     Hybrid Journal   (Followers: 3)
Chemical Research in Toxicology     Full-text available via subscription   (Followers: 17)
Chemical Reviews     Full-text available via subscription   (Followers: 128)
Chemical Science     Open Access   (Followers: 18)
Chemical Technology     Open Access   (Followers: 11)
Chemical Vapor Deposition     Hybrid Journal   (Followers: 4)
Chemical Week     Full-text available via subscription   (Followers: 7)
Chemie in Unserer Zeit     Hybrid Journal   (Followers: 52)
Chemie-Ingenieur-Technik (Cit)     Hybrid Journal   (Followers: 25)
ChemInform     Hybrid Journal   (Followers: 4)
Chemistry & Biodiversity     Hybrid Journal   (Followers: 5)
Chemistry & Biology     Full-text available via subscription   (Followers: 29)
Chemistry & Industry     Hybrid Journal   (Followers: 3)
Chemistry - A European Journal     Hybrid Journal   (Followers: 115)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 12)
Chemistry and Materials Research     Open Access   (Followers: 15)
Chemistry Central Journal     Open Access   (Followers: 5)
Chemistry Education Research and Practice     Free   (Followers: 4)
Chemistry in Education     Open Access   (Followers: 2)
Chemistry International     Hybrid Journal   (Followers: 1)
Chemistry Letters     Full-text available via subscription   (Followers: 43)
Chemistry of Materials     Full-text available via subscription   (Followers: 144)
Chemistry of Natural Compounds     Hybrid Journal   (Followers: 8)
Chemistry-Didactics-Ecology-Metrology     Open Access  
ChemistryOpen     Open Access   (Followers: 1)
Chemkon - Chemie Konkret, Forum Fuer Unterricht Und Didaktik     Hybrid Journal  
Chemoecology     Hybrid Journal   (Followers: 2)
Chemometrics and Intelligent Laboratory Systems     Hybrid Journal   (Followers: 15)
Chemosensors     Open Access  
ChemPhysChem     Hybrid Journal   (Followers: 6)
ChemTexts     Hybrid Journal  
CHIMIA International Journal for Chemistry     Full-text available via subscription   (Followers: 3)
Chinese Journal of Chemistry     Hybrid Journal   (Followers: 6)
Chinese Journal of Polymer Science     Hybrid Journal   (Followers: 10)
Chromatographia     Hybrid Journal   (Followers: 24)
Chromatography     Open Access   (Followers: 5)
Chromatography Research International     Open Access   (Followers: 5)
Clay Minerals     Full-text available via subscription   (Followers: 9)
Cogent Chemistry     Open Access  
Colloid and Interface Science Communications     Open Access  
Colloid and Polymer Science     Hybrid Journal   (Followers: 8)
Colloids and Surfaces B: Biointerfaces     Hybrid Journal   (Followers: 6)
Combinatorial Chemistry & High Throughput Screening     Hybrid Journal   (Followers: 4)
Combustion Science and Technology     Hybrid Journal   (Followers: 19)
Comments on Inorganic Chemistry: A Journal of Critical Discussion of the Current Literature     Hybrid Journal   (Followers: 1)
Composite Interfaces     Hybrid Journal   (Followers: 3)
Comprehensive Chemical Kinetics     Full-text available via subscription   (Followers: 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: 10)
Computational Biology and Chemistry     Hybrid Journal   (Followers: 9)
Computational Chemistry     Open Access   (Followers: 2)
Computers & Chemical Engineering     Hybrid Journal   (Followers: 9)
Coordination Chemistry Reviews     Full-text available via subscription  
Copernican Letters     Open Access  
Critical Reviews in Biochemistry and Molecular Biology     Hybrid Journal   (Followers: 4)
Crystal Structure Theory and Applications     Open Access   (Followers: 2)
CrystEngComm     Full-text available via subscription   (Followers: 7)
Current Catalysis     Hybrid Journal   (Followers: 1)
Current Metabolomics     Hybrid Journal   (Followers: 3)
Current Opinion in Colloid & Interface Science     Hybrid Journal   (Followers: 7)
Current Opinion in Molecular Therapeutics     Full-text available via subscription   (Followers: 13)
Current Research in Chemistry     Open Access   (Followers: 7)
Current Science     Open Access   (Followers: 35)
Dalton Transactions     Full-text available via subscription   (Followers: 17)
Detection     Open Access   (Followers: 2)
Developments in Geochemistry     Full-text available via subscription   (Followers: 1)
Diamond and Related Materials     Hybrid Journal   (Followers: 12)
Dislocations in Solids     Full-text available via subscription  
Doklady Chemistry     Hybrid Journal  
Drying Technology: An International Journal     Hybrid Journal   (Followers: 3)
Eclética Química     Open Access   (Followers: 1)
Ecological Chemistry and Engineering S     Open Access   (Followers: 2)
Ecotoxicology and Environmental Contamination     Open Access  
Educación Química     Open Access   (Followers: 1)
Education for Chemical Engineers     Hybrid Journal   (Followers: 4)
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]   [27 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
   Published by Elsevier Homepage  [3039 journals]
  • Preliminary MALDI-TOF-MS analysis of seminal plasma N-glycome of infertile
           men
    • Abstract: Publication date: Available online 18 September 2016
      Source:Carbohydrate Research
      Author(s): Anna Kałuża, Anna Jarząb, Andrzej Gamian, Ewa M. Kratz, Mariusz Zimmer, Mirosława Ferens-Sieczkowska
      Glycosylation pattern within reproductive tract is now suggested to be involved in providing female immune tolerance for allograft sperm and developing embryo, but the information whether impaired glycosylation may influence male fertility potential is still limited. We have analyzed seminal plasma N-glycome in pooled samples derived from fertile and infertile men by means of MALDI-TOF/TOF tandem mass spectrometry. Among infertile subjects, normozoospermic, oligozoospermic, asthenozoospermic and oligoasthenozoospermic samples were obtained. Eighty-six oligosaccharides were identified in all the analyzed samples. Differences in the content of unique glycans: high mannose and hybrid type, lacking terminal sialic acid and highly fucosylated were found when samples derived from infertile subjects with different semen patterns were compared to the fertile control. The content of highly branched glycans was 3-fold elevated in normozoospermic infertile men, while the expression of highly fucosylated oligosaccharides was increased in asthenozoospermic, oligozoospermic and oligoasthenozoospermic samples. Sialylation of oligosaccharides was decreased in oligozoospermic, oligoasthenozoospermic and especially asthenozoospermic samples, but increased in infertile normozoospermic subjects. Altered glycosylation observed in seminal plasma may reflect similar changes in sperm surface glycoproteins, and may disturb sperm interaction with female immune system. We suggest that at least some cases of unexplained male infertility may be associated with impaired glycosylation.
      Graphical abstract image

      PubDate: 2016-09-23T17:38:08Z
       
  • Total synthesis and the anticancer activity of (+)-spisulosine
    • 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
       
  • Diastereoselective synthesis of furanose and pyranose substituted glycine
           and alanine derivatives via proline-catalyzed asymmetric α-amination of
           aldehydes
    • 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
       
  • Structural features of N-glycans linked to glycoproteins expressed in
           three kinds of water plants: Predominant occurrence of the plant complex
           type N-glycans bearing Lewis a epitope
    • Abstract: Publication date: Available online 17 September 2016
      Source:Carbohydrate Research
      Author(s): Maeda Megumi, Misato Tani, Takeo Yoshiie, Christopher J. Vavricka, Yoshinobu Kimura
      The Japanese cedar pollen allergen (Cry j1) and the mountain cedar pollen allergen (Jun a1) are glycosylated with plant complex type N-glycans bearing Lewis a epitope(s) (Galβ1-3[Fucα1-4]GlcNAc-). The biological significance of Lewis a type plant N-glycans and their effects on the human immune system remain to be elucidated. Since a substantial amount of such plant specific N-glycans are required to evaluate immunological activity, we have searched for good plant-glycan sources to characterize Lewis a epitope-containing plant N-glycans. In this study, we have found that three water plants, Elodea nuttallii, Egeria densa, and Ceratophyllum demersum, produce glycoproteins bearing Lewis a units. Structural analysis of the N-glycans revealed that almost all glycoproteins expressed in these three water plants predominantly carry plant complex type N-glycans including the Lewis a type, suggesting that these water plants are good sources for preparation of Lewis a type plant N-glycans in substantial amounts.
      Graphical abstract image

      PubDate: 2016-09-18T09:45:20Z
       
  • Editorial board
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433




      PubDate: 2016-09-18T09:45:20Z
       
  • Graphical contents list
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433




      PubDate: 2016-09-18T09:45:20Z
       
  • Solvent-free bismuth oxycarbonate-mediated mechanochemical glycosylation:
           A simple greener alternative to access O-/S-glycosides efficiently
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Kashmir Prasad Sethi, K.P. Ravindranathan Kartha
      Preparation of a variety of per-O-acylated O- and S-glycosides of a set of commonly encountered mono- and disaccharides has been achieved effectively by solvent-free grinding of the corresponding acetylated/benzoylated glycosyl bromide and the desired acceptor alcohol/thiol in the presence of bismuth carbonate in a planetary ball mill. The method is simple, requires short reaction time periods and is practical allowing it to be performed at a milligram-to multi-gram scale as required. In the cases where the product is crystalline, it was often obtained in practically pure form by crystallization (and without the need for chromatographic isolation).
      Graphical abstract image

      PubDate: 2016-09-18T09:45:20Z
       
  • New insights into Nod factor biosynthesis: Analyses of chitooligomers and
           lipo-chitooligomers of Rhizobium sp. IRBG74 mutants
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Véréna Poinsot, Matthew B. Crook, Stéphanie Erdn, Fabienne Maillet, Adeline Bascaules, Jean-Michel Ané
      Soil-dwelling, nitrogen-fixing rhizobia signal their presence to legume hosts by secreting lipo-chitooligomers (LCOs) that are decorated with a variety of chemical substituents. It has long been assumed, but never empirically shown, that the LCO backbone is synthesized first by NodC, NodB, and NodA, followed by addition of one or more substituents by other Nod proteins. By analyzing a collection of in-frame deletion mutants of key nod genes in the bacterium Rhizobium sp. IRBG74 by mass spectrometry, we were able to shed light on the possible substitution order of LCO decorations, and we discovered that the prevailing view is probably erroneous. We found that most substituents could be transferred to a short chitin backbone prior to acylation by NodA, which is probably one of the last steps in LCO biosynthesis. The existence of substituted, short chitin oligomers offers new insights into symbiotic plant–microbe signaling.
      Graphical abstract image

      PubDate: 2016-09-18T09:45:20Z
       
  • One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to
           polyhydroxy oxohexanenitrile: A versatile methodology for the facile
           access of azasugar alkaloids
    • 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
       
  • Getting a grip on glycans: A current overview of the metabolic
           oligosaccharide engineering toolbox
    • Abstract: Publication date: Available online 16 September 2016
      Source:Carbohydrate Research
      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: 2016-09-18T09:45:20Z
       
  • Non-exchanging hydroxyl groups on the surface of cellulose fibrils: The
           role of interaction with water
    • Abstract: Publication date: Available online 10 September 2016
      Source:Carbohydrate Research
      Author(s): Erik L. Lindh, Malin Bergenstråhle-Wohlert, Camilla Terenzi, Lennart Salmén, István Furó
      The interaction of water with cellulose stages many unresolved questions. Here 2H MAS NMR and IR spectra recorded under carefully selected conditions in 1H 2H exchanged, and re-exchanged, cellulose samples are presented. It is shown here, by a quantitative and robust approach, that only two of the three available hydroxyl groups on the surface of cellulose fibrils are exchanging their hydrogen with the surrounding water molecules. This finding is additionally verified and explained by MD simulations which demonstrate that the 1HO(2) and 1HO(6) hydroxyl groups of the constituting glucose units act as hydrogen-bond donors to water, while the 1HO(3) groups behave exclusively as hydrogen-bond acceptors from water and donate hydrogen to their intra-chain neighbors O(5). We conclude that such a behavior makes the latter hydroxyl group unreactive to hydrogen exchange with water.
      Graphical abstract image

      PubDate: 2016-09-18T09:45:20Z
       
  • Preparation of glycosyl thiourea derivatives from glycosyl azides using
           sulfamic acid and sodium iodide in one-pot
    • Abstract: Publication date: Available online 7 September 2016
      Source:Carbohydrate Research
      Author(s): Arin Gucchait, Manas Jana, Kuladip Jana, Anup Kumar Misra
      Novel one-pot reaction conditions have been developed for the preparation of glycosyl thiourea derivatives directly from glycosyl azides mediated by a combination of sulfamic acid and sodium iodide. The reaction conditions were clean, non-toxic and the products were isolated in good to excellent yield.
      Graphical abstract image

      PubDate: 2016-09-10T22:53:33Z
       
  • Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands
    • 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
       
  • Convenient stereocontrolled amidoglycosylation of alcohols with acetylated
           glycals and trichloroethoxysulfonamide
    • Abstract: Publication date: Available online 4 September 2016
      Source:Carbohydrate Research
      Author(s): Teiichi Murakami, Yukari Sato, Kyoko Yoshioka, Mutsuo Tanaka
      A regio- and stereo-controlled, rhodium(II)-catalyzed amidoglycosylation of alcohols has been developed using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene. This one-pot amidoglycosylation was applied to a variety of primary and secondary alcohols to afford the β-O-glycosides with acceptable yields up to 84%. The reaction would proceed via stereoselective intermolecular aziridination of the glycal from the α-face followed by SN2 reaction with alcohol at C-1 from the β-face to give 1,2:2,3-di-trans-substituted isomer only.
      Graphical abstract image

      PubDate: 2016-09-06T22:41:36Z
       
  • Site-directed mutagenesis of bacterial cellulose synthase highlights
           sulfur–arene interaction as key to catalysis
    • Abstract: Publication date: Available online 29 August 2016
      Source:Carbohydrate Research
      Author(s): Shi-jing Sun, Yoshiki Horikawa, Masahisa Wada, Junji Sugiyama, Tomoya Imai
      Cellulose is one of the most abundant biological polymers on Earth, and is synthesized by the cellulose synthase complex in cell membranes. Although many cellulose synthase genes have been identified over the past 25 years, functional studies of cellulose synthase using recombinant proteins have rarely been conducted. In this study, we conducted a functional analysis of cellulose synthase with site-directed mutagenesis, by using recombinant cellulose synthase reconstituted in living Escherichia coli cells that we recently constructed (cellulose-synthesizing E. coli, CESEC). We demonstrated that inactivating mutations at an important amino acid residue reduced cellulose production. In this study, an interesting loss-of-function mutation occurred on Cys308, whose main chain carbonyl plays an important role for locating the cellulose terminus. Mutating this cysteine to serine, thus changing sulfur to oxygen in the side chain, abolished cellulose production in addition to other apparent detrimental mutations. This unexpected result highlights that the thiol side-chain of this cysteine plays an active role in catalysis, and additional mutation experiments indicated that the sulfur–arene interaction around Cys308 is a key in cellulose-synthesizing activity. Data obtained by CESEC shed light on the function of cellulose synthase in living cells, and will deepen our understanding of the mechanism of cellulose synthase.
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      PubDate: 2016-09-01T22:20:00Z
       
  • Synthesis and structure of a carbohydrate-fused [15]-macrodilactone
    • Abstract: Publication date: Available online 29 August 2016
      Source:Carbohydrate Research
      Author(s): Debjani Si, Mark W. Peczuh
      The design, synthesis and structural characterization of a new α-D-glucose fused [15]-macrodilactone is reported. The macrolide was synthesized by a route involving sequential acylations of glucose at the C4′ and C6′ hydroxyl groups followed by an intramolecular Stille reaction previously established for other [15]-macrodilactones. Analysis of the X-ray crystallographic structure of the macrolide revealed a unique conformation of this macrocycle that differs from earlier models for [13]- and [15]-macrodilactones. Organizing the three planar units and the pyranose moiety into a macrocyclic ring resulted in a cup-shaped structure with planar chirality. Further, the gt conformation of the exocyclic hydroxymethyl group in the glucose unit was found to be crucial for controlling the planar chirality and, hence, governing the molecular shape and overall topology of the compound.
      Graphical abstract image

      PubDate: 2016-09-01T22:20:00Z
       
  • Novel dextran derivatives with unconventional structure formed in an
           efficient one-pot reaction
    • Abstract: Publication date: Available online 27 August 2016
      Source:Carbohydrate Research
      Author(s): Konrad Hotzel, Thomas Heinze
      An efficient one-pot synthesis of new dextran derivatives is described. The functional groups of β-alanine, i.e., the carboxyl- and amine group, are converted independently in one-step by iminium chloride to form products with a single substituent. The dextran N-[(dimethylamino)methylene]-β-alanine ester is formed selectively. The structure of the resulting polymers is unambiguously determined by means of NMR- and FTIR-spectroscopy and elemental analysis.
      Graphical abstract image

      PubDate: 2016-08-28T22:09:11Z
       
  • Structural elucidation of polysaccharide containing 3-O-methyl galactose
           from fruiting bodies of Pleurotus citrinopileatus
    • Abstract: Publication date: Available online 28 August 2016
      Source:Carbohydrate Research
      Author(s): Pengfei He, Anqiang Zhang, Saijing Zhou, Fuming Zhang, Robert J. Linhardt, Peilong Sun
      A water-soluble polysaccharide containing 3-O-methyl galactose (PCP60W) was isolated from fruiting bodies of Pleurotus citrinopileatus and purified by anion-exchange and gel column chromatography. This polysaccharide has an average molecular weight of 2.74 × 104 Da and its structure was elucidated using monosaccharide composition and methylation analysis combined with one- and two-dimensional (COSY, TOCSY, NOESY, HMQC and HMBC) NMR spectroscopy. PCP60W was shown to be a linear partially 3-O-methylated α-galactopyranan comprised of 6-linked galactose, 6-linked 3-O-methyl galactose and 4-linked glucose in a ratio of 3.0:1.0:0.6. This work provides additional evidence for the view that 3-O-methyl galactose is common to the genus Pleurotus.
      Graphical abstract image

      PubDate: 2016-08-28T22:09:11Z
       
  • Direct assay for endo-α-mannosidase substrate preference on correctly
           folded and misfolded model glycoproteins
    • Abstract: Publication date: Available online 28 August 2016
      Source:Carbohydrate Research
      Author(s): Simone Dedola, Masayuki Izumi, Yutaka Makimura, Akira Seko, Akiko Kanamori, Yoichi Takeda, Yukishige Ito, Yasuhiro Kajihara
      We previously reported a unique assay system for UDP-glucose glycoprotein glucosyltransferase (UGGT) toward glycoprotein folding intermediates during the folding process. The assay involved the in vitro folding of both high-mannose type oligosaccharyl crambin, which yielded only the correctly folded glycoprotein form (M9-glycosyl-native-crambin), and its mutant, which yielded misfolded glycoproteins (M9-glycosyl-misfolded-crambin), in the presence of UGGT. The process successfully yielded both mono-glucosylated M9-glycosyl-native-crambin (G1M9-glycosyl-native-crambin) and M9-glycosyl-misfolded-crambin (G1M9-glycosyl-misfolded-crambin). Here, we report the use of our in vitro folding system to evaluate the substrate preference of Golgi endo-α-mannosidase against G1M9-native and -misfolded glycoprotein forms. In our assay Golgi endo-α-mannosidase removed Glc-α-1-3-Man unit from G1M9-native and -misfolded-crambins clearly proving that Golgi endo-α-mannosidase does not have specific preference for correctly folded or misfolded protein structure.
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      PubDate: 2016-08-28T22:09:11Z
       
  • Biosynthetic and synthetic access to amino sugars
    • Abstract: Publication date: Available online 24 August 2016
      Source:Carbohydrate Research
      Author(s): Kornelia Skarbek, Maria J. Milewska
      Amino sugars are important constituents of a number of biomacromolecules and products of microbial secondary metabolism, including antibiotics. For most of them, the amino group is located at the positions C1, C2 or C3 of the hexose or pentose ring. In biological systems, amino sugars are formed due to the catalytic activity of specific aminotransferases or amidotransferases by introducing an amino functionality derived from L-glutamate or L-glutamine to the keto forms of sugar phosphates or sugar nucleotides. The synthetic introduction of amino functionalities in a regio- and stereoselective manner onto sugar scaffolds represents a substantial challenge. Most of the modern methods of for the preparation of 1-, 2- and 3-amino sugars are those starting from “an active ester” of carbohydrate derivatives, glycals, alcohols, carbonyl compounds and amino acids. A substantial progress in the development of region- and stereoselective methods of amino sugar synthesis has been made in the recent years, due to the application of metal-based catalysts and tethered approaches. A comprehensive review on the current state of knowledge on biosynthesis and chemical synthesis of amino sugars is presented.
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      PubDate: 2016-08-25T00:40:47Z
       
  • Recent research progress on preparation and application of N, N,
           N-trimethyl chitosan
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Meiyan Wu, Zhu Long, Huining Xiao, Cuihua Dong
      N,N,N-trimethyl chitosan (TMC) is a quaternized chitosan derivative with excellent solubility in aqueous solutions. It has been extensively studied as an absorption enhancer, antibacterial agent and gene vector due to its ability to form complexes with anionic gels or macromoleculars. However, the research which describes the process of TMC preparation and its new applications has not been fully reviewed. In this paper, recent progress regarding different TMC preparation methods and its characterization and application in different fields is presented. Key findings are compared and summarized and some topics for further study are suggested.
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      PubDate: 2016-08-25T00:40:47Z
       
  • Altered gene expression of glycosyltransferases and sialyltransferases and
           total amount of glycosphingolipids following herpes simplex virus
           infection
    • Abstract: Publication date: Available online 18 August 2016
      Source:Carbohydrate Research
      Author(s): Kazuki Miyaji, Jun-ichi Furukawa, Youichi Suzuki, Naoki Yamamoto, Yasuro Shinohara, Nobuhiro Yuki
      There is a case report of a patient with overlapping Guillain–Barré syndrome and Bickerstaff brainstem encephalitis after infection with herpes simplex virus type 1 (HSV-1), who carried high titers of serum anti-GQ1b IgG antibodies. Several studies have linked viral infection to the modulation of ganglioside expression such as human T-lymphotropic virus to GD2 and simian virus 40 to GM3. Also, enhancement of the expression of GM2 on the cell membrane after cytomegalovirus infection has been reported. The objective of this study was to unveil the relationship between HSV-1 infection and the alteration of cellular ganglioside expression in neuronal and glial cell lines. In addition to these cell lines, several human tumor cell lines including astrocytoma cells, neuroblastoma cells, T-cell leukemia cells and kidney cells derived from normal human and monkey were infected with HSV-1 as well as HSV-2. To measure changes in ganglioside-related gene expressions and gangliosides levels in cells, quantitative PCR and glycosphingolipid-glycomic analysis were performed. Changes in gene expression of glycosyltransferases and sialyltransferases were observed in HSV-1 and HSV-2-infected cells, although with different trends. 39 glycosphingolipid-glycans were quantitatively analyzed. HSV-1 and HSV-2 infections resulted in changes in the total amount of gangliosides depending on the cell lines used and type of virus. Qualitative changes caused by each infection of HSV-1 and HSV-2 were almost negligible.
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      PubDate: 2016-08-20T00:28:39Z
       
  • Synthesis and glycosidase inhibition evaluation of
           (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol
    • Abstract: Publication date: Available online 9 August 2016
      Source:Carbohydrate Research
      Author(s): En Zhang, Peng-Yan Bai, Wei Sun, Shang Wang, Ming-Ming Wang, Shuai-Min Xu, Hong-Min Liu
      A new azasugar (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol (1) was obtained from commercially available d-glucose using one-pot reductive cyclization as a key step. The target product, i.e., the iminosugar isomer, was obtained in 10 steps and 24.3% overall yield. Only three column chromatography purifications were needed in this synthesis. The biological activity of the target molecule as glycosidase inhibitor was studied, but the inhibitory activity against four glycosidases was not good (IC50 > 100 μM).
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      PubDate: 2016-08-12T15:03:35Z
       
  • Structure of repeating unit of the capsular polysaccharide from
           Acinetobacter baumannii D78 and assignment of the K4 gene cluster
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Johanna J. Kenyon, Immacolata Speciale, Ruth M. Hall, Cristina De Castro
      The structure of the K4 capsular polysaccharide (CPS) from a multiply antibiotic resistant Acinetobacter baumannii isolate D78 was elucidated by chemical and spectroscopical analysis. The K4 repeating unit is composed entirely by aminosugars and the trisaccharide repeating unit of the backbone polysaccharide is branched with a terminal N-acetyl-galactosamine capped with pyruvate as cyclic acetal. Each residue is in the pyranose form, α configured at the anomeric center, and has the D absolute configuration. The genes responsible for the synthesis of the K4 repeat unit and its polymerization and export are found in the capsule locus KL4 present in D78. The pyruvate acetal addition to galactosamine is formed by Ptr1, a novel pyruvate transferase, encoded at this locus.
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      PubDate: 2016-08-08T14:45:27Z
       
  • Structure of polysaccharide moiety of Pseudomonas xanthomarina KMM 1447T
           lipopolysaccharide
    • Abstract: Publication date: Available online 30 July 2016
      Source:Carbohydrate Research
      Author(s): Maxim S. Kokoulin, Svetlana V. Tomshich, Anatoly I. Kalinovskiy, Lyudmila A. Romanenko, Nadezhda A. Komandrova
      The structural analysis of a polysaccharide moiety of Pseudomonas xanthomarina KMM 1447T lipopolysaccharide (LPS) was carried out. Mild acid degradation of LPS resulted in identification of two polysaccharides. The major one was built of β-D-GlcpNAcA residues amidated with L-Ala and Gly residues randomly. The minor polysaccharide was composed of branched tetrasaccharide repeating units constituted by two D-Galр, D-GalpNAc and ether of D-Glc with (2R,4R)-2,4-dihydroxypentanoic acid lactone (2R,4R-Dhpl): →3)-α-D-Galр-(1 → 3)-β-D-Galр-(1 → 3)-[β-D-Glcp4(2R,4R-Dhpl)-(1 → 4)]-β-D-GalpNAc-(1 → .
      Graphical abstract image

      PubDate: 2016-08-04T14:30:44Z
       
  • Graphical contents list
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432




      PubDate: 2016-08-04T14:30:44Z
       
  • Editorial board
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432




      PubDate: 2016-08-04T14:30:44Z
       
  • The O-antigen of Plesiomonas shigelloides serotype O36 containing
           pseudaminic acid
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Marta Kaszowska, Katarina Stojkovic, Tomasz Niedziela, Czeslaw Lugowski
      The structure of the repeating unit of O-antigen of Plesiomonas shigelloides serotype O36 has been investigated by 1H and 13C NMR spectroscopy, matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry and chemical methods. The new structure of trisaccharide has been established: →4)-β-Pse5Ac7(R3Hb)-(2 → 4)-β-D-Galp-(1 → 3)-β-D-GlcpNAc-(1→ These trisaccharide O-antigen units substitute the core undecasaccharide at C-4 of the β-D-GlcpNAc residue. The core oligosaccharide and lipid A are identical with these of the serotype O17 (PCM 2231) (Maciejewska, A., Lukasiewicz, J., Kaszowska, M., Jachymek, W., Man-Kupisinska, A.; Lugowski, C. Mar. Drugs. 2013, 11 (2), 440–454; Lukasiewicz, J., Dzieciatkowska, M., Niedziela, T., Jachymek, W., Augustyniuk, A., Kenne, L., Lugowski, C. Biochemistry, 2006, 45, 10434–10447).
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      PubDate: 2016-08-04T14:30:44Z
       
  • The impact of aminopyrene trisulfonate (APTS) label in acceptor glycan
           
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Stephan Goetz, Martin Rejzek, Sergey A. Nepogodiev, Robert A. Field
      Aminopyrene trisulfonate (APTS)-labelled disaccharides are demonstrated to serve as readily accessible acceptor substrates for galactosyltransferase activities present in Arabidopsis microsome preparations. The reductive amination procedure used to install the fluorophore results in loss of the ring structure of the reducing terminal sugar unit, such that a single intact sugar ring is present, attached via an alditol tether to the aminopyrene fluorophore. The configuration of the alditol portion of the labelled acceptor, as well as the position of alditol galactosylation, substantially influence the ability of compounds to serve as Arabidopsis galactosyltransferase acceptor substrates. The APTS label exhibits an unexpected reaction-promoting effect that is not evident for structurally similar sulfonated aromatic fluorophores ANDS and ANTS. When APTS-labelled β-(1 → 4)-Gal3 was employed as an acceptor substrate with Arabidopsis microsomes, glycan extension generated β-(1 → 4)-galactan chains running to beyond 60 galactose residues. These studies demonstrate the potential of even very short glycan-APTS probes for assessing plant galactosyltransferase activities and the suitability CE-LIF for CAZyme profiling.
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      PubDate: 2016-08-04T14:30:44Z
       
  • Sequence analysis of the pyruvylated galactan sulfate-derived
           oligosaccharides by negative-ion electrospray tandem mass spectrometry
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Na Li, Wenjun Mao, Xue Liu, Shuyao Wang, Zheng Xia, Sujian Cao, Lin Li, Qi Zhang, Shan Liu
      Five sulfated oligosaccharide fragments, F1–F5, were prepared from a pyruvylated galactan sulfate from the green alga Codium divaricatum, by partial depolymerization using mild acid hydrolysis and purification with gel-permeation chromatography. Negative-ion electrospray tandem mass spectrometry with collision-induced dissociation (ES-CID-MS/MS) is attempted for sequence determination of the sulfated oligosaccharides. The sequence of F1 with homogeneous disaccharide composition was first characterized to be Galp-(4SO4)-(1 → 3)-Galp by detailed nuclear magnetic resonance spectroscopic analyses. The fragmentation pattern of F1 in the product ion spectra was established on the basis of negative-ion ES-CID MS/MS, which was then applied to sequence analysis of other sulfated oligosaccharides. The sequences of F2 and F3 were deduced to be Galp-(4SO4)-(1 → 3)-Galp-(1 → 3)-Galp-(1 → 3)-Galp and 3,4-O-(1-carboxyethylidene)-Galp-(6SO4)-(1 → 3)-Galp, respectively. The sequences of major fragments in F4 and F5 were also deduced. The investigation demonstrated that negative-ion ES-CID-MS/MS was an efficient method for the sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides which revealed the patterns of substitution and glycosidic linkages. The pyruvylated galactan sulfate-derived oligosaccharides were novel sulfated oligosaccharides different from other algal polysaccharide-derived oligosaccharides.
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      PubDate: 2016-07-29T14:07:10Z
       
  • 1,3-Dipolar cycloaddition of a cyclic nitrone derived from
           2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem
           antibiotics
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Michał Pieczykolan, Olga Staszewska-Krajewska, Bartłomiej Furman, Marek Chmielewski
      1,3-Dipolar cycloadditions of 2-deoxy-D-ribose-derived L-threo five-membered cyclic nitrone to α,β-unsaturated γ- and δ-lactones were investigated. Cycloadducts obtained from δ-lactones, after N O bond cleavage, opening of the lactone ring, and protection of hydroxyl groups were subjected to β-lactam ring formation by using Mukaiyama's salt. Cycloadducts from γ-lactones subjected to the same reaction sequence undergo β-elimination of a water molecule to provide pyrrolidine-substituted unsaturated γ-lactones.
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      PubDate: 2016-07-29T14:07:10Z
       
  • Stryphnosides G–P, 10 new triterpene glycosides from the pericarps of
           Stryphnodendron fissuratum
    • Abstract: Publication date: Available online 28 July 2016
      Source:Carbohydrate Research
      Author(s): Akihito Yokosuka, Genki Okabe, Satoru Tatsuno, Yoshihiro Mimaki
      Ten new triterpene glycosides, stryphnosides G–P (1–10), were isolated from the pericarps of Stryphnodendron fissuratum (Legminosae). The structures of 1–10 were determined based on spectroscopic analyses, including various two-dimensional NMR spectroscopic techniques, and the results of hydrolytic cleavage. The sugar moiety attached to C-3 of the aglycone of 4, 5, and 7–10 is composed of five or six monosaccharides, of which the terminal α-L-arabinosyl unit has a 1C4 conformation. Compounds 2 and 5 differ from the other isolates in having an α-L-rhamnosyl unit at the C-21 hydroxy group. The cytotoxic activity of 1–10, stryphnosides A–F (11–16), and their aglycones (1a, 11a, 14a, and 16a) against HL-60 cells was also examined.
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      PubDate: 2016-07-29T14:07:10Z
       
  • Conformational flexibility around the Gal-β-(1 → 3)-Glc linkage:
           Experimental evidence for the existence of the anti-ψ conformation in
           aqueous solution
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Paloma Vidal, Jesús Jiménez-Barbero, Juan F. Espinosa
      NOE-based analysis of the disaccharide β-Gal-(1 → 3)-β-Glc-OMe (1), especially a diagnostic Gal1–Glc4 NOE detected in a HSQC-NOESY spectrum, reveals the existence of the anti-ψ conformer in aqueous solution in addition to the major syn conformer. This result provides experimental proof of conformational flexibility around the aglyconic bond of β-(1 → 3) disaccharides, in contrast to previous studies that suggested that the flexibility around this linkage was restricted to the syn conformational region.
      Graphical abstract image

      PubDate: 2016-07-25T13:58:46Z
       
  • Kinetic analysis for the isomerization of cellobiose to cellobiulose in
           subcritical aqueous ethanol
    • Abstract: Publication date: Available online 11 July 2016
      Source:Carbohydrate Research
      Author(s): Nontanut Soisangwan, Da-Ming Gao, Takashi Kobayashi, Pramote Khuwijitjaru, Shuji Adachi
      The isomerization of cellobiose to cellobiulose, and other degradation reactions of cellobiose were investigated in subcritical aqueous ethanol with concentrations of ethanol ranging from 0 to 60% (w/w) and at temperatures ranging from 170 to 200 °C. The maximum yield of cellobiulose (ca. 40%) was obtained from the treatment of cellobiose in 60% (w/w) aqueous ethanol at 190 °C. Glucose and fructose were also detected as byproducts. The concentration-time integral method was employed to analyze the rate constants for the isomerization and degradation processes. The rate constant of cellobiose isomerization to cellobiulose was greater than those of the degradation reactions under all experimental conditions, and it increased significantly with treatment temperature and ethanol concentration. However, the use of higher temperatures and ethanol concentrations was restricted due to decomposition of the saccharides and the low solubility of cellobiose, respectively. The effect of initial feed concentration (0.5–5.5% w/w) was also studied. The maximum productivity of cellobiulose, 54.1 kg/(h m3-reactor), was accomplished at a feed concentration of 5.5% (w/w) in 20% (w/w) subcritical aqueous ethanol.
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      PubDate: 2016-07-14T13:17:08Z
       
  • Efficient isomerization of methyl arabinofuranosides into corresponding
           arabinopyranosides in presence of pyridine
    • Abstract: Publication date: Available online 12 July 2016
      Source:Carbohydrate Research
      Author(s): Sunchu Prabhakar, Loïc Lemiègre, Thierry Benvegnu, Srinivas Hotha, Vincent Ferrières, Laurent Legentil
      Fisher glycosylation, the oldest but efficient reaction towards alkyl glycosides, suffers nonetheless from lack of selectivity, especially when dealing with pentoses. In this case, a mixture of the four isomers, namely the furanosides and the pyranosides, is formed. According to previous studies, the rate and selectivity of the reaction depend greatly on the reaction time and the temperature. In this report, another factor was evaluated, the introduction of a weak nucleophilic base. Interestingly, addition of pyridine few hours after the reaction has started allowed rapid isomerization of the methyl pentofuranosides into its pyranoside counterparts. The reaction proceeds with great diastereoselectivity using arabinose, ribose, xylose and lyxose as starting pentoses. Corresponding methyl pyranosides were obtained as the sole isomers with yields ranging from 65% to 75%.
      Graphical abstract image

      PubDate: 2016-07-14T13:17:08Z
       
  • Human milk oligosaccharides: The role in the fine-tuning of innate immune
           responses
    • Abstract: Publication date: Available online 7 July 2016
      Source:Carbohydrate Research
      Author(s): Anna Kulinich, Li Liu
      In order to secure the health of newborns over the period of immune immaturity during the first months of life, a mother provides her offspring with passive protection: bioactive molecules transferred through the placenta and breast milk. It is well known that human milk contains immunoglobulins (Ig), immune cells and diverse cytokines, which affect newborn directly or indirectly and contribute to the maturation of immune system. However, in addition to the above-stated molecules, human milk oligosaccharides (HMOs), a complex mixture of free indigestible carbohydrates with multiple functions, play exceptional roles in the functioning of the infants' immune system. These biological molecules have been studied over decades, however, interest in HMOs does not seem to have abated. Although biological activities of oligosaccharides from human milk have been explicitly reviewed, information regarding the role of HMOs in inflammation remains rather fragmented. The purpose of this review is to compile existing knowledge about the role of certain species of HMOs, including fucosylated, galactosylated and sialylated oligosaccharides, and their signaling pathways in immunity and inflammation. The advances in applying this information to the treatment of diseases in infants as well as adults we also reviewed.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Synthesis of C-glycosyl triazolyl quinoline-based fluorescent sensors for
           the detection of mercury ions
    • Abstract: Publication date: Available online 7 July 2016
      Source:Carbohydrate Research
      Author(s): Lingfang Wang, Jianzhong Jin, Linwei Zhao, Hongyun Shen, Chao Shen, Pengfei Zhang
      A series of novel C-glycosyl triazolyl quinoline-based fluorescent sensors have been synthesized via click chemistry. It was found that novel sensors exhibited good selectivity for Hg2+ over many other metal ions. The glucose framework was introduced to increase the water-solubility of the fluorescent sensors and broaden its application for the detection of Hg(II) in the water-solubility biological systems. The mechanism of the chemodosimetric behavior of the sensors has been attributed to a binding mode of triazolyl quinoline with Hg2+ which has been characterized by a number of spectroscopic techniques.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Hyaluronic acid Auto-Crosslinked Polymer (ACP): Reaction Monitoring,
           Process Investigation and Hyaluronidase Stability
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Stefano Pluda, Mauro Pavan, Devis Galesso, Cristian Guarise
      Hyaluronic Acid (HA) is a non-sulphated glycosaminoglycan that, despite its high molecular weight, is soluble in water and is not resistant to enzymatic degradation, the latter of which hinders its wider application as a biomedical material. Auto-crosslinked polymer (ACP) gels of HA are fully biocompatible hydrogels that exhibit improved viscoelastic properties and prolonged in vivo residence times compared to the native polymer. Crosslinking is achieved through a base-catalysed reaction consisting of the activation of HA carboxyl groups by 2-chloro-1-methylpyridinium iodide (CMPI) and subsequent nucleophilic acyl substitution by the hydroxyl groups of HA in organic solvent. In this study, a number of ACP hydrogels have been obtained via reactions using varying ratios of CMPI to HA. The crosslinking reaction was monitored by rheological measurements in organic solvents during CMPI addition to the reaction mixture. The ACP intermediates, powders and hydrogels were characterized, helping to elucidate the crosslinking process. A two-step mechanism was proposed to explain the observed trends in viscosity and particle size. Syntheses were carried out by varying the reaction temperature, respectively at 0 °C, 25 °C and 45 °C in N-Methyl-2-Pyrrolidone (NMP), as well as the solvent respectively in NMP, DMSO and DMF at 25 °C. Interestingly, varying these parameters did not substantially affect the degree of crosslinking but likely did influence the intra/inter-molecular crosslinking ratio and, therefore, the viscoelastic properties. A wide range of crosslinking densities was confirmed through ESEM analysis. Finally, a comparative hyaluronidase degradation assay revealed that the ACPs exhibited a higher resistance toward enzymatic cleavage at low elastic modulus compared to other more chemically resistant, crosslinked HAs. These observations demonstrated the importance of crosslinking density of matrix structures on substrate availability.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Synthesis of a suite of click-compatible sugar analogs for probing
           carbohydrate metabolism
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Bo Wang, Daniel D. McClosky, Charles T. Anderson, Gong Chen
      Metabolic labeling based on the click chemistry between alkynyl and azido groups offers a powerful tool to study the function of carbohydrates in living systems, including plants. Herein, we describe the chemical synthesis of six alkynyl-modified sugars designed as analogs to D-glucose, D-mannose, L-rhamnose and sucrose present in plant cell walls. Among these new alkynyl probes, four of them are the 6-deoxy-alkynyl analogs of the corresponding sugars and do not possess any 6-OH groups. The other two are based on a new structural design, in which an ethynyl group is incorporated at the C-6 position of the sugar and the 6-OH group remains. The synthetic routes for both types of probes share common aldehyde intermediates, which are derived from the corresponding 6-OH precursor with other hydroxy groups protected. The overall synthesis sequence of these probes is efficient, concise, and scalable.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Structural investigation of the lipopolysaccharide O-chain isolated from
           Burkholderia fungorum strain DSM 17061
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Antonia De Felice, Flaviana Di Lorenzo, Kirstin Scherlach, Claudia Ross, Alba Silipo, Christian Hertweck, Antonio Molinaro
      Gram-negative bacteria exhibit lipopolysaccharides (LPSs) on their outer membrane surface. LPS is considered one of the most potent bacterial virulence factors. Here we report the elucidation of the LPS O-chain structure isolated from Burkholderia fungorum, a bacterium isolated from the white-rot fungus Phanerochaete chrysosporium that can act as a pathogen for plants and domesticated animals. The structure was determined by the employment of detailed chemical and NMR spectroscopy analyses as the following:
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      PubDate: 2016-07-10T13:09:16Z
       
  • A novel analytical method for D-glucosamine quantification and its
           application in the analysis of chitosan degradation by a minimal enzyme
           cocktail
    • Abstract: Publication date: Available online 4 July 2016
      Source:Carbohydrate Research
      Author(s): Sophanit Mekasha, Hana Toupalová, Eka Linggadjaja, Harish A. Tolani, Ladislav Anděra, Magnus Ø. Arntzen, Gustav Vaaje-Kolstad, Vincent G.H. Eijsink, Jane W. Agger
      Enzymatic depolymerization of chitosan, a β-(1,4)-linked polycationic polysaccharide composed of D-glucosamine (GlcN) and N-acetyl-D-glucosamine (GlcNAc) provides a possible route to the exploitation of chitin-rich biomass. Complete conversion of chitosan to mono-sugars requires the synergistic action of endo- and exo- chitosanases. In the present study we have developed an efficient and cost-effective chitosan-degrading enzyme cocktail containing only two enzymes, an endo-attacking bacterial chitosanase, ScCsn46A, from Streptomyces coelicolor, and an exo-attacking glucosamine specific β-glucosaminidase, Tk-Glm, from the archaeon Thermococcus kodakarensis KOD1. Moreover, we developed a fast, reliable quantitative method for analysis of GlcN using high performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD). The sensitivity of this method is high and less than 50 pmol was easily detected, which is about 1000-fold better than the sensitivity of more commonly used detection methods based on refractive index. We also obtained qualitative insight into product development during the enzymatic degradation reaction by means of ElectroSpray Ionization-Mass Spectrometry (ESI-MS).
      Graphical abstract image

      PubDate: 2016-07-06T13:02:08Z
       
  • Novel biologically active series of N-acetylglucosamine derivatives for
           the suppressive activities on GAG release
    • Abstract: Publication date: Available online 5 July 2016
      Source:Carbohydrate Research
      Author(s): Tingting Cao, Yong Li, Lijuan Jiang, Li Yuan, Lin Dong, Ying Li, Shufan Yin
      (d)-Glucosamine and other nutritional supplements have emerged as safe alternative therapies for osteoarthritis, a chronic and degenerative articular joint disease. N-acetyl-(d)-glucosamine, a compound that can be modified at the N position, is considered to improve the oral bioavailability of (d)-glucosamine and has been proven to possess greater in vitro chondroprotective activity compared with the parent agent. In this study, to further utilize these properties, we focus on the modification of the N position with a benzenesulfonyl and different isoxazole formyl groups. Among these compounds, the 3-(2-chlorobenzene)-5-methyl-isoxazole formyl chloride and p-methoxybenzenesulfonyl chloride modifying structures proved to be the most active of the series and efficiently processed the chondrocytes in vitro. These novel N-position substitution compounds may represent promising leads for osteoarthritis drug development.
      Graphical abstract image

      PubDate: 2016-07-06T13:02:08Z
       
  • Structure determination of Streptococcus suis serotype 9 capsular
           polysaccharide and assignment of functions of the cps locus genes involved
           in its biosynthesis
    • Abstract: Publication date: Available online 5 July 2016
      Source:Carbohydrate Research
      Author(s): Evgueny Vinogradov, Guillaume Goyette-Desjardins, Masatoshi Okura, Daisuke Takamatsu, Marcelo Gottschalk, Mariela Segura
      Streptococcus suis serotype 9 is the most prevalent S. suis serotype in several European countries. In spite of its pathogenicity for pigs and increasing zoonotic potential, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 9 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence: [3)Glcol-6-P-3-[D-Gal(α1-2)]D-Gal(β1-3)D-Sug(β1-3)L-Rha(α1-)] n . Compared to previously characterized S. suis CPS (serotypes 1, 1/2, 2 and 14), serotype 9 CPS does not contain sialic acid but contains a labile 4-keto sugar (2-acetamido-2,6-dideoxy-β-D-xylo-hexopyranos-4-ulose), one particular feature of this serotype. A correlation between S. suis serotype 9 CPS sequence and genes of this serotype cps locus encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotype 9.
      Graphical abstract image

      PubDate: 2016-07-06T13:02:08Z
       
  • Application of amylomaltase for the synthesis of salicin-α-glucosides as
           efficient anticoagulant and anti-inflammatory agents
    • Abstract: Publication date: Available online 29 June 2016
      Source:Carbohydrate Research
      Author(s): Prakarn Rudeekulthamrong, Jarunee Kaulpiboon
      The focus of this study was the synthesis of α-glucosyl derivatives of salicin by a transglucosylation reaction. The reaction was catalyzed by recombinant amylomaltase using tapioca starch as a glucosyl donor. Several reaction parameters, such as the enzyme-substrate concentrations, pH, temperature and incubation time, were optimized. Using the optimum conditions, at least three products with retention times (R t) of 6.2, 9.2 and 14.1 were observed. The maximum yield of glucosylated salicin derivatives was 63% (w/w) of the total products. The structures of the glucosylated salicin derivatives were confirmed to be salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside through a combination of enzyme treatments, mass spectrometry and NMR analyses. The glycosidic bond between glucose units consisted of an α-1,4-configuration. The water solubility of salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside was 3-, 5- and 8-fold higher, respectively, than that of salicin, whereas their relative sweetness values were lower than that of sucrose. Interestingly, the long-chain salicin-α-D-glucosides showed greater anticoagulant and anti-inflammatory activities than salicin. In addition, the synthesized salicin-α-D-glucosides were able to tolerate acidic and high temperature conditions, but not α-glucosidase or human digestive enzymes. Therefore, these salicin-α-D-glucosides should be applied by the injection route to achieve greater bioavailability than is possible by the oral route.
      Graphical abstract image

      PubDate: 2016-07-02T10:15:23Z
       
  • An integrated 3D-printed platform for the automated isolation of N-glycans
    • Abstract: Publication date: Available online 30 June 2016
      Source:Carbohydrate Research
      Author(s): Mao-Mao Wang, Pedro Laborda, Louis Patrick Conway, Xu-Chu Duan, Kun Huang, Li Liu, Josef Voglmeir
      The development of techniques for the rapid analysis of N-glycans is a key step in enabling the roles of glycoproteins in biological processes to be studied. Analysis is usually performed through the liberation of the carbohydrate moieties from proteins, followed by fluorescent labeling and identification using either standardized HPLC or mass spectrometry techniques. A simple and robust automated process for the release and isolation of N-glycans would greatly improve analytical throughput and reproducibility, and is thus highly desirable. Inspired by the increasing number of reported projects involving open source labware, which allows the design and construction of otherwise inaccessible laboratory equipment using low-cost 3D printers, we used this technique to fabricate a platform for the automated isolation of N-glycans. As a proof of concept, we demonstrated the successful recovery of glycan samples from the glycoprotein model fetuin using our self-made 3D-printed equipment.
      Graphical abstract image

      PubDate: 2016-07-02T10:15:23Z
       
  • Synthesis of part structures of Cryptococcus neoformans serotype C
           capsular polysaccharide
    • Abstract: Publication date: Available online 1 July 2016
      Source:Carbohydrate Research
      Author(s): Lorenzo Guazzelli, Orla McCabe, Stefan Oscarson
      Cryptococcus neoformans is a fungal pathogen that can cause life-threatening infections in immunocompromised patients. The development of a vaccine based on the capsular polysaccharide of C. neoformans is still an open challenge due to the heterogeneity of the capsular polysaccharide and the difficulty of identifying protective epitopes. Therefore, construction of structurally defined part structures of the C. neoformans GXM capsule is in great demand. Herein is presented the synthesis of a 3-O-naphthalenylmethyl protected trisaccharide thioglycoside building block which is present in C. neoformans serotype C polysaccharide. Its property as a donor in a glycosylation reaction with a model acceptor has been evaluated together with its behaviour as an acceptor following removal of the temporary protecting group. The heavily branched hexasaccharide was obtained in good yields and excellent α-selectivity. The frame shifted octasaccharide structural triad motif for serotype C was also prepared following the same building block strategy. For the first time this structural motif, which is the most substituted amongst the four C. neoformans serotypes, was prepared. Three synthesized C. neoformans serotype C fragments of varying size, from penta-up to octasaccharide, were deprotected and will be included in unique glycoarrays to further investigate the possibility to develop a synthetic vaccine against this pathogen.
      Graphical abstract image

      PubDate: 2016-07-02T10:15:23Z
       
  • Structure of the O-specific polysaccharides of Pseudomonas chlororaphis
           subsp. chlororaphis UCM B-106
    • Abstract: Publication date: Available online 1 July 2016
      Source:Carbohydrate Research
      Author(s): Evelina L. Zdorovenko, Alexandra A. Kadykova, Liudmyla D. Varbanets, Alexander S. Shashkov, Elena A. Kiprianova, Oksana S. Brovarskaya, Yuriy A. Knirel
      O-specific polysaccharide was obtained from the lipopolysaccharide of Pseudomonas chlororaphis subsp. chlororaphis UCM B-106 and studied by composition analysis along with 1D and 2D 1H and 13C NMR spectroscopy. The polysaccharide was found to contain a derivative of pseudaminic acid (Pse) and the following structure of the trisaccharide repeating unit was established. →4)-β-Psep5Ac7Hb-(2 → 6)-β-d-Galf-(1 → 3)-β-d-Galp-(1 → . Where Pse5Ac7Hb indicates 5-acetamido-3,5,7,9-tetradeoxy-7-[(R)-3-hydroxybutanoylamino]-l-glycero-l-manno-non-2-ulosonic acid.
      Graphical abstract image

      PubDate: 2016-07-02T10:15:23Z
       
  • The first asymmetric synthesis of marliolide from readily accessible
           carbohydrate as chiral template
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Karabasappa Mailar, Won Jun Choi
      A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the β-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, β-hydroxyl γ-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate.
      Graphical abstract image

      PubDate: 2016-06-27T15:11:49Z
       
  • Functional analysis of anomeric sugar kinases
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Louis P. Conway, Josef Voglmeir
      Anomeric sugar kinases perform fundamental roles in the metabolism of carbohydrates. Under- or overexpression of these enzymes, or mutations causing functional impairments can give rise to diseases such as galactosaemia and so the study of this class of kinase is of critical importance. In addition, anomeric sugar kinases which are naturally promiscuous, or have been artificially made so, may find application in the synthesis of libraries of drug candidates (for example, antibiotics), and natural or unnatural oligosaccharides and glycoconjugates. In this review, we provide an overview of the biological functions of these enzymes, the tools which have been developed to investigate them, and the current frontiers in their study.
      Graphical abstract image

      PubDate: 2016-06-27T15:11:49Z
       
  • A one-pot synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by
           hydrodeoxygenation of xylose using a palladium catalyst
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Michael A. Jackson, Judith A. Blackburn, Neil P.J. Price, Karl E. Vermillion, Steven C. Peterson, Gregory M. Ferrence
      In an effort to expand the number of biobased chemicals available from sugars, xylose has been converted to 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane in a one-pot reaction using palladium supported on silica-alumina as the catalyst. The title compound is produced in 35–40% yield under 7 MPa H2 pressure at 733 K using 3–10 wt%Pd on silica-alumina catalyst. It is isolated using a combination of liquid-liquid extractions and flash chromatography. This dimer can be converted to its monomer, 2-hydroxy-(2-hydroxymethyl)tetrahydrofuran, which ring opens under acid conditions to 1,5-dihydroxy-2-pentanone. This diol can then be esterified with vinylacetate in phosphate buffer to produce 1,5-bis(acetyloxy)-2-pentanone which is an inhibitor of mammalian 11β-hydroxysteroid dehydrogenase 1. 1H and 13C nmr spectra of each of these species are reported. The single crystal X-ray structure of the title compound is also reported. These data were collected in a temperature range of 100 K–273 K and show a solid state phase change from triclinic to monoclinic between 175 K and 220 K without a conformational change.
      Graphical abstract image

      PubDate: 2016-06-23T14:53:40Z
       
 
 
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