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    9945 results match your criteria Carbohydrate research[Journal]

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    Synthesis of a trisaccharide repeating unit of the O-antigen from Burkholderia cenocepacia and its dimer.
    Carbohydr Res 2017 Sep 8;451:1-11. Epub 2017 Sep 8.
    National Glycoengineering Research Center, Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 27 Shanda Nan Lu, Jinan 250010, PR China. Electronic address:
    The trisaccharide repeating unit of an O-antigen derived from Burkholderia cenocepacia and its dimer, i.e., α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (1) and α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-(1 → 4)-α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (2), respectively, were synthesized via a highly convergent strategy. Read More

    The trehalose-specific transporter LpqY-SugABC is required for antimicrobial and anti-biofilm activity of trehalose analogues in Mycobacterium smegmatis.
    Carbohydr Res 2017 Aug 9;450:60-66. Epub 2017 Aug 9.
    Department of Chemistry and Biochemistry, Central Michigan University, Mount Pleasant, MI 48859, United States. Electronic address:
    Mycobacteria, including the bacterial pathogen that causes human tuberculosis, possess distinctive pathways for synthesizing and utilizing the non-mammalian disaccharide trehalose. Trehalose metabolism is essential for mycobacterial viability and has been linked to in vitro biofilm formation, which may bear relevance to in vivo drug tolerance. Previous research has shown that some trehalose analogues bearing modifications at the 6-position inhibit growth of various mycobacterial species. Read More

    An acceptor analogue of β-1,4-galactosyltransferase: Substrate, inhibitor, or both?
    Carbohydr Res 2017 Aug 31;450:54-59. Epub 2017 Aug 31.
    King's College London, Department of Chemistry, Faculty of Natural & Mathematical Sciences, Britannia House, 7 Trinity Street, London, SE1 1DB, UK. Electronic address:
    Many glycosyltransferase inhibitors in the literature are structurally derived from the donor or acceptor substrate of the respective enzyme. A representative example is 2-naphthyl β-d-GlcNAc, a synthetic GlcNAc glycoside that has been reported as a galactosyltransferase inhibitor. This GlcNAc derivative is attractive as a chemical tool compound for biological and biochemical studies because of its reported potency as an inhibitor, and its short and straightforward synthesis from readily available starting materials. Read More

    Synthesis of a series of new glycoclusters and the evaluation of their anti-adhesion activities.
    Carbohydr Res 2017 Sep 1;450:49-53. Epub 2017 Sep 1.
    State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xueyuan Road, Haidian District, Beijing 100191, PR China. Electronic address:
    According to our early researches, some glycoclusters having glucose, mannose, cellose and lactose residues showed good anti-adhesion activity of leukocytes to endothelial cells and exerted anti-inflammatory effects. Based on these results and combination principles of drugs, a series of new glycoclusters modifying with potentially anti-oxidant activity pharmacophores have been synthesized, and their anti-adhesion activities were assessed by static state cell-based adhesion assay. The results showed that some modified glycoclusters displayed better activities than their leading compound. Read More

    Rational optimization of the mannoside building block for automated electrochemical assembly of the core trisaccharide of GPI anchor oligosaccharides.
    Carbohydr Res 2017 Aug 25;450:44-48. Epub 2017 Aug 25.
    Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan; Center for Research on Green Sustainable Chemistry, Faculty of Engineering, Tottori University, Japan. Electronic address:
    We have developed a carbohydrate building block of mannosides based on DFT calculations, electrochemical analysis, and automated solution-phase synthesis. The optimized building block in hand was used to prepare the core trisaccharide of GPI anchor oligosaccharides. Read More

    Alternate synthesis to d-glycero-β-d-manno-heptose 1,7-biphosphate.
    Carbohydr Res 2017 Aug 24;450:38-43. Epub 2017 Aug 24.
    Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, Ontario, K1A 0R6, Canada.
    d-glycero-β-d-manno-heptose 1,7-biphosphate (HBP) is an enzymatic intermediate in the biosynthesis of the heptose component of lipopolysaccharide (LPS), and was recently revealed to be a pathogen-associated molecular pattern (PAMP) that allows detection of Gram-negative bacteria by the mammalian immune system. Cellular detection of HBP depends upon its stimulation of a cascade that leads to the phosphorylation and assembly of the TRAF-interacting with forkhead-associated domain protein A (TIFA), which activates the transcription factor NF-κB. In this note, an alternate chemical synthesis of HBP is described and its biological activity is established, providing pure material for further assessing and exploiting the biological activity of this compound. Read More

    Synthesis of a model trisaccharide for studying the interplay between the anti α-Gal antibody and the trans-sialidase reactions in Trypanosoma cruzi.
    Carbohydr Res 2017 Aug 18;450:30-37. Epub 2017 Aug 18.
    Universidad de Buenos Aires, Consejo Nacional de Investigaciones Científicas y Técnicas, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Buenos Aires, Argentina. Electronic address:
    Trypanosoma cruzi, the etiologic agent of Chagas disease, is covered by a dense glycocalix mainly composed by glycoproteins called mucins which are also the acceptors of sialic acid in a reaction catalyzed by a trans-sialidase (TcTS). Sialylation of trypomastigote mucins protects the parasite from lysis by the anti α-Galp antibodies from serum. The TcTS is essential for the infection process since T. Read More

    Membrane-enclosed multienzyme (MEME) synthesis of 2,7-anhydro-sialic acid derivatives.
    Carbohydr Res 2017 Aug 19. Epub 2017 Aug 19.
    Quadram Institute Bioscience, The Gut Health and Food Safety Institute Strategic Programme, Norwich Research Park, Norwich NR4 7UA, UK. Electronic address:
    Naturally occurring 2,7-anhydro-alpha-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac) is a transglycosylation product of bacterial intramolecular trans-sialidases (IT-sialidases). A facile one-pot two-enzyme approach has been established for the synthesis of 2,7-anhydro-sialic acid derivatives including those containing different sialic acid forms such as Neu5Ac and N-glycolylneuraminic acid (Neu5Gc). The approach is based on the use of Ruminoccocus gnavus IT-sialidase for the release of 2,7-anhydro-sialic acid from glycoproteins, and the conversion of free sialic acid by a sialic acid aldolase. Read More

    Genetic and structural elucidation of capsular polysaccharides from Streptococcus pneumoniae serotype 23A and 23B, and comparison to serotype 23F.
    Carbohydr Res 2017 Aug 18;450:19-29. Epub 2017 Aug 18.
    LimmaTech Biologics AG, Grabenstrasse 3, Schlieren, Switzerland.
    Streptococcus pneumoniae is a globally important encapsulated human pathogen with approximately 100 different serotypes recognized. Serogroup 23 consists of serotype 23F, present in licensed vaccines, and emerging serotypes 23A and 23B. Here, we report the previously unknown structures of the pneumococcal capsular polysaccharides serotype 23A and 23B determined using genetic analysis, NMR spectroscopy, composition and linkage analysis and Smith degradation (of polysaccharide 23A). Read More

    Chemical synthesis of guanosine diphosphate mannuronic acid (GDP-ManA) and its C-4-O-methyl and C-4-deoxy congeners.
    Carbohydr Res 2017 Aug 11;450:12-18. Epub 2017 Aug 11.
    Bio-organic Synthesis Group, Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands. Electronic address:
    Described is the first synthesis of guanosine diphosphate mannuronic acid (GDP-ManA), the sugar donor used by algae and bacteria for the production of alginate, an anionic polysaccharide composed of β-d-mannuronic acid (ManA) and α-l-guluronic acid (GulA). Understanding the biosynthesis of these polyanionic polysaccharides on the molecular level, opens up avenues to use and modulate the biosynthesis machinery for biotechnological and therapeutic applications. The synthesis reported here delivers multi-milligram amounts of the GDP-ManA donor that can be used to study the polymerase (Alg8 in Pseudomonas aeruginosa) that generates the poly-ManA chain. Read More

    A carbon tetrachloride-free synthesis of N-phenyltrifluoroacetimidoyl chloride.
    Carbohydr Res 2017 Aug 10;450:10-11. Epub 2017 Aug 10.
    School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria, 3010, Australia. Electronic address:
    N-Phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) is a reagent widely used for the preparation of glycosyl N-phenyltrifluoroacetimidates. However, the most commonly applied method requires carbon tetrachloride, a hepatotoxic reagent that has been phased out under the Montreal Protocol. We report a new synthesis of N-phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) using dichlorotriphenylphosphane and triethylamine. Read More

    One-pot synthesis of oxazolidine-2-thione and thiozolidine-2-thione from sugar azido-alcohols.
    Carbohydr Res 2017 Aug 4;450:1-9. Epub 2017 Aug 4.
    Department of Chemistry, Indian Institute of Technology (IIT), Banaras Hindu University, Varanasi 221005, India. Electronic address:
    A controlled and facile synthesis of various glycosyl 1,3-oxazolidine-2-thiones and 1,3- thiozolidine-2-thiones has been accomplished from corresponding sugar azido alcohols utilizing Staudinger reaction (PPh3 and CS2) via isothiocynate route. A series of reactions were performed to investigate the effects of CS2 and PPh3 on the selectivity of product formed. The excessive addition of CS2 with PPh3(1. Read More

    Erylosides F8, V1-V3, and W-W2 - New triterpene oligoglycosides from the Carribean sponge Erylus goffrilleri.
    Carbohydr Res 2017 Sep 4;449:153-159. Epub 2017 Aug 4.
    G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Division of the Russian Academy of Science, 690022, Vladivostok, Russia.
    Seven new triterpene glycosides, erylosides F8 (1), V1 (2), V2 (3), V3 (4), W (5), W1 (6) and W2 (7), were isolated from a Carribean sponge Erylus goffrilleri collected from the Carribean Sea near the Arrecife-Seco reef (Cuba). Structures of the glycosides were determined using (1)H and (13)C NMR spectroscopy, including 2D NMR procedures ((1)H-(1)H COSY, (1)H-(13)С HMBC, (1)H-(13)С HSQC and NOESY) and HR ESI mass spectrometry. Erylosides 1 and 4 have 14-carboxy-24,25-dimethyllanost-8(9)-en-3β,25-diol as aglycone whereas glycosides 2, 3, 5, 6 and 7 are 14-carboxy-24-acetoxy-24-methyllanost-8(9)-en-3β-ol glycoconjugates. Read More

    Glycoconjugate probes containing a core-fucosylated N-glycan trisaccharide for fucose lectin identification and purification.
    Carbohydr Res 2017 Sep 3;449:143-152. Epub 2017 Aug 3.
    CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Rd, Pudong, Shanghai, 201203, China; University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing, 100049, China. Electronic address:
    Glyco-PAMAM dendrimers and glyco-agarose beads bearing a core-fucosylated N-glycan trisaccharide GlcNAcβ1,4(Fucα1,6)GlcNAc or a non-fucose disaccharide GlcNAcβ1,4GlcNAc were successfully synthesized and characterized by monosaccharide analysis with HPAEC-PAD technique. These glycoconjugates as fucose lectin probes were applied in fucose-specific lectin detection and purification. The model fucose lectin AAL indicated binding activity with the FITC-labeled PAMAM carrying core-fucose trisaccharide. Read More

    Pyruvylated cell wall glycopolymers of Promicromonospora citrea VKM A≿-665(T) and Promicromonospora sp. VKM A≿-1028.
    Carbohydr Res 2017 Sep 27;449:134-142. Epub 2017 Jul 27.
    All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region 142290, Russian Federation.
    The cell walls of two strains of the genus Promicromonospora (phylum Actinobacteria) were found to include non-phosphorylated anionic glycopolymers with pyruvic acid acetals of R-configuration. The cell wall of the type strain P. citrea 665(T) contains two glycopolymers of the sort, including the Kdn-teichulosonic acid with the repeating unit →6)-α-d-Gl≿p/→6)-α-d-Gl≿p3SO3(-)-(1 → 4)-α-[7,9Pyr]-Kdn-(2→, and the galactan with the repeating unit →3)-α-[4,6Pyr]-d-Galp-2OAc-(1 → . Read More

    Enzymatic synthesis of ribo- and 2'-deoxyribonucleosides from glycofuranosyl phosphates: An approach to facilitate isotopic labeling.
    Carbohydr Res 2017 Sep 20;449:125-133. Epub 2017 Jul 20.
    Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556-5670 USA. Electronic address:
    Milligram quantities of α-D-ribofuranosyl 1-phosphate (sodium salt) (αR1P) were prepared by the phosphorolysis of inosine, catalyzed by purine nucleoside phosphorylase (PNPase). The αR1P was isolated by chromatography in >95% purity and characterized by (1)H and (13)C NMR spectroscopy. Aqueous solutions of αR1P were stable at pH 6. Read More

    Physakengoses K-Q, seven new sucrose esters from Physalis alkekengi var. franchetii.
    Carbohydr Res 2017 Sep 28;449:120-124. Epub 2017 Jul 28.
    State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, 210009, PR China. Electronic address:
    Seven sucrose esters, physakengoses K-Q (1-7) were isolated from the aerial parts of Physalis alkekengi var. franchetii. Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical methods. Read More

    Characteristic oligosaccharides released from acid hydrolysis for the structural analysis of chondroitin sulfate.
    Carbohydr Res 2017 Sep 26;449:114-119. Epub 2017 Jul 26.
    School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, PR China; National Engineering Research Center of Seafood, Dalian Polytechnic University, Dalian 116034, PR China; National & Local Joint Engineering Laboratory for Marine Bioactive Polysaccharide Development and Application, Dalian Polytechnic University, Dalian 116034, PR China. Electronic address:
    Because the glycosidic linkage of uronic acid is most resistant to acid, oligosaccharides may be formed during the acid hydrolysis of acidic polysaccharides. To take chondroitin sulfate (CS) as an example of acidic polysaccharides, the present study characterized the oligosaccharides released through acid hydrolysis and demonstrated their usefulness for structural confirmation. Acid hydrolysates of commercial standard CSs from shark cartilage and porcine bone were elucidated using HPLC-MS(n) after 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization, and altogether 11 di-, tri- and tetra-saccharides with or without sulfate/acetyl groups were identified by their multi-stage mass spectra. Read More

    Cellodextrin phosphorylase from Ruminiclostridium thermocellum: X-ray crystal structure and substrate specificity analysis.
    Carbohydr Res 2017 Jul 21. Epub 2017 Jul 21.
    Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK. Electronic address:
    The GH94 glycoside hydrolase cellodextrin phosphorylase (CDP, EC 2.4.1. Read More

    Tunable stereoselectivity in the synthesis of α- and β-aryl glycosides using 1,2-α-anhydrosugars as glycosyl donors.
    Carbohydr Res 2017 Sep 25;449:95-102. Epub 2017 Jul 25.
    B. S. Abdur Rahman Crescent University, Vandalur, Chennai, India. Electronic address:
    The stereochemical course of O-glycosidation of 1,2-α-d-anhydrosugars (glycal epoxides) with phenols can be tuned by varying the metal ion of the base. While the reaction of 1,2-α-d-anhydrosugars with phenols mediated by trimethylaluminium leads exclusively to 1,2-cis-α-O-aryl glycosides, similar reaction mediated by caesium carbonate gives exclusively 1,2-trans-β-O-aryl glycosides. In contrast, reaction with phenoxides generated from Grignard reagent and calcium salts affords mixture of the anomers. Read More

    Evaluation of hydrogen bond networks in cellulose Iβ and II crystals using density functional theory and Car-Parrinello molecular dynamics.
    Carbohydr Res 2017 Sep 5;449:103-113. Epub 2017 Jul 5.
    Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-Ku, Yokohama 240-8501, Japan.
    Crystal models of cellulose Iβ and II, which contain various hydrogen bonding (HB) networks, were analyzed using density functional theory and Car-Parrinello molecular dynamics (CPMD) simulations. From the CPMD trajectories, the power spectra of the velocity correlation functions of hydroxyl groups involved in hydrogen bonds were calculated. For the Iβ allomorph, HB network A, which is dominant according to the neutron diffraction data, was stable, and the power spectrum represented the essential features of the experimental IR spectra. Read More

    A comparative study on the activity of fungal lytic polysaccharide monooxygenases for the depolymerization of cellulose in soybean spent flakes.
    Carbohydr Res 2017 Sep 18;449:85-94. Epub 2017 Jul 18.
    Department of Chemical and Biochemical Engineering, Center for Bioprocess Engineering, Technical University of Denmark, Søltofts Plads, Building 229, Kgs. Lyngby, 2800, Denmark. Electronic address:
    Lytic polysaccharide monooxygenases (LPMOs) are copper-dependent enzymes capable of the oxidative breakdown of polysaccharides. They are of industrial interest due to their ability to enhance the enzymatic depolymerization of recalcitrant substrates by glycoside hydrolases. In this paper, twenty-four lytic polysaccharide monooxygenases (LPMOs) expressed in Trichoderma reesei were evaluated for their ability to oxidize the complex polysaccharides in soybean spent flakes, an abundant and industrially relevant substrate. Read More

    Gram scale synthesis of A (type 2) and B (type 2) blood group tetrasaccharides through 1,6-anhydro-N-acetyl-β-D-glucosamine.
    Carbohydr Res 2017 Sep 27;449:65-84. Epub 2017 Jun 27.
    Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya str. 16/10, Moscow 117997, Russian Federation. Electronic address:
    Gram scale synthesis of A (type 2) and B (type 2) tetrasaccharides in the form of 3-aminopropyl glycosides is proposed starting from 3-O-benzoyl-1,6-anhydro-N-acetylglucosamine. Its galactosylation followed by re-protection gave lactosamine derivative with single free 2'-OH group in total yield 75%. Standard fucosylation and next run of re-protection in total yield 88% gave a trisaccharide Fuc-Gal-anhydroGlcNAc with single free 3'-OH group. Read More

    Structural characterization of glucosylated lactose derivatives synthesized by the Lactobacillus reuteri GtfA and Gtf180 glucansucrase enzymes.
    Carbohydr Res 2017 Sep 8;449:59-64. Epub 2017 Jul 8.
    Microbial Physiology, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands.
    Glucansucrase enzymes from lactic acid bacteria are receiving strong interest because of their wide range of gluco-oligosaccharide and polysaccharide products from sucrose, some of which have prebiotic potential. Glucansucrases GtfA and Gtf180 from Lactobacillus reuteri strains are known to convert sucrose into α-glucans with different types of linkages, but also to use other molecules as acceptor substrates. Here we report that incubation of (N-terminally truncated versions of) these enzymes with lactose plus sucrose resulted in synthesis of at least 5 glucosylated lactose products of a degree of polymerization (DP) of 3-4. Read More

    Anti-inflammatory effect of sugar-amino acid Maillard reaction products on intestinal inflammation model in vitro and in vivo.
    Carbohydr Res 2017 Sep 11;449:47-58. Epub 2017 Jul 11.
    Department of Biotechnology, College of Life Science & Biotechnology, Korea University, Seoul, 136-713, South Korea. Electronic address:
    The Maillard reaction is a nonenzymatic reaction between an amino acid and a reducing sugar that usually occurs upon heating. This reaction occurs routinely in cooking, generates numerous products, which are collectively referred to as Maillard reaction products (MRPs) contributing to aroma and color features. Advanced glycation end-products (AGEs) transformed from MRPs are participated in many types of inflammation reaction. Read More

    Elucidating biochemical features and biological roles of Streptomyces proteins recognizing crystalline chitin- and cellulose-types and their soluble derivatives.
    Carbohydr Res 2017 Aug 20;448:220-226. Epub 2017 Jun 20.
    FB Biology/Chemistry, University Osnabrück, Barbarastr. 13, 49069 Osnabrück, Germany. Electronic address:
    Pioneering biochemical, immunological, physiological and microscopic studies in combination with gene cloning allowed uncovering previously unknown genes encoding proteins of streptomycetes to target crystalline chitin and cellulose as well as their soluble degradation-compounds via binding protein dependent transporters. Complementary analyses provoked an understanding of novel regulators governing transcription of selected genes. These discoveries induced detecting close and distant homologues of former orphan proteins encoded by genes from different bacteria. Read More

    Exhaustive rotamer search of the (4)C1 conformation of α- and β-d-galactopyranose.
    Carbohydr Res 2017 Aug 6;448:136-147. Epub 2017 May 6.
    Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Consejo Nacional de Investigaciones Científicas y Técnicas, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Departamento de Química Orgánica, Pab. 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina. Electronic address:
    An exhaustive search approach was used to establish all possible rotamers of α- and β-d-galactopyranose using DFT at the B3LYP/6-311+G** and M06-2X/6-311+G** levels, both in vacuum calculations, and including two variants of continuum solvent models as PCM and SMD to simulate water solutions. Free energies were also calculated. MM3 was used as the starting point for calculations, using a dielectric constant of 1. Read More

    Agarose based large molecular systems: Synthesis of fluorescent aromatic agarose amino acid nano-conjugates - their pH-stimulated structural variations and interactions with BSA.
    Carbohydr Res 2017 Sep 26;449:37-46. Epub 2017 Jun 26.
    Marine Biotechnology and Ecology Division, Anusandhan Bhavan, 2 Rafi Marg, New Delhi 110001, India; Academy of Scientific & Innovative Research, Anusandhan Bhavan, 2 Rafi Marg, New Delhi 110001, India. Electronic address:
    Two new nano-sized fluorescent 6-amino agarose naphthalic acid half ester derivatives were synthesized (ca.60% yields) employing 1,8- and 2,3-naphthalic acid anhydrides (1,8-AANE, and 2,3-AANE respectively). These large nano molecular frameworks (DLS 3 & 100 nm, and 3 & 152 nm respectively) contains amino, naphthalate half-ester carboxyl groups at the C-6 positions of the 1,3-β-D-galactopyranose moieties of the agarose backbone (overall DS 0. Read More

    Characterization of the O-antigen polysaccharide derived from Pantoea agglomerans IG1 lipopolysaccharide.
    Carbohydr Res 2017 Sep 28;449:32-36. Epub 2017 Jun 28.
    Faculty of Medicine, Kagawa University, Miki-cho, Kita-gun, Kagawa, Japan; Research Institute for Healthy Living, Niigata University of Pharmacy and Applied Life Sciences, Akiba-ku, Niigata, Japan; Control of Innate Immunity TRA, Bio-Lab, Kagawa, Japan.
    A polysaccharide fraction was isolated from the Pantoea agglomerans IG1 lipopolysaccharide (IP-PA1), and its O-antigenic polysaccharide was characterized by chemical analyses and 1D and 2D (1)H and (13)C NMR spectroscopy. The polysaccharide is composed of linear tetrasaccharide repeating units, consisting of glucose and rhamnose, where 40% of one of the rhamnose residues is substituted with glucose: →2)-α-l-Rhap-(1→6)-α-d-Glcp-(1→2)-[β-d-Glcp-(1→3)]0.4-α-l-Rhap-(1→2)-α-l-Rhap-(1→. Read More

    Sulfated polysaccharides of the Vietnamese brown alga Sargassum aquifolium (Fucales, Sargassaceae).
    Carbohydr Res 2017 Sep 27;449:23-31. Epub 2017 Jun 27.
    N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation. Electronic address:
    A fucoidan preparation named FSA was isolated from the brown alga Sargassum aquifolium collected from the coastal waters of Vietnam. l-Fucose, d-galactose, d-mannose, d-glucuronic acid, d-xylose, and sulfate were found to be the main constituents of FSA. The preparation was fractionated by anion-exchange chromatography on DEAE-Sephacel eluted stepwise with 0. Read More

    Structures and gene clusters of the O-antigens of Escherichia albertii O3, O4, O6, and O7.
    Carbohydr Res 2017 Sep 17;449:17-22. Epub 2017 Jun 17.
    State Key Laboratory of Infectious Disease Prevention and Control, National Institute for Communicable Disease Control and Prevention, Chinese Center for Disease Control and Prevention, Changping, Beijing, China; Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Hangzhou, China. Electronic address:
    The O-specific polysaccharides (OPSs) called O-antigens were obtained by mild acid degradation of the lipopolysaccharides of Escherichia albertii serotypes O3, O4, O6, and O7 and studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure was established for the OPS of E. albertii O4, which, to our knowledge, is unique among known bacterial polysaccharide structures: →2)-α-l-Rhap-(1 → 2)-α-l-Fucp-(1 → 2)-β-d-Galp-(1 → 3)-α-d-GalpNAc-(1 → 3)-β-d-GlcpNAc-(1→ The OPS structure of the strain of E. Read More

    Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides.
    Carbohydr Res 2017 Sep 20;449:11-16. Epub 2017 Jun 20.
    Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA. Electronic address:
    With the aid of a series of model thioether or thioglycoside containing polyols protected with combinations of benzyl ethers and 2-naphthylmethyl ethers it is demonstrated that the latter are readily cleaved selectively under hydrogenolytic conditions in the presence of the frequently catalyst-poisoning sulfides. These results suggest the possibility of employing 2-naphthylmethyl ethers in place of benzyl ethers in synthetic schemes when hydrogenolytic deprotection is anticipated in the presence of thioether type functionality. Read More

    N-glycan structures of β-HlH subunit of Helix lucorum hemocyanin.
    Carbohydr Res 2017 Sep 22;449:1-10. Epub 2017 Jun 22.
    Laboratory of Protein Biochemistry and Biomolecular Engineering, Ghent University, KL Ledeganckstraat 35, Ghent 9000, Belgium.
    The carbohydrate structures of molluscan hemocyanins have recently received particular interest due to their specific monosaccharide composition, as well as their immunostimulatory properties and application in clinical studies. For the first time, we investigated N-glycans of the structural subunit β-HlH of hemocyanin isolated from Helix lucorum. In total, 32 different glycans were enzymatically liberated and characterized by tandem mass spectrometry using a Q-Trap mass spectrometer. Read More

    Imaging of protein-specific glycosylation by glycan metabolic tagging and in situ proximity ligation.
    Carbohydr Res 2017 Aug 27;448:148-154. Epub 2017 Jun 27.
    Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, College of Life Sciences, Zhejiang University, Hangzhou 310058, China. Electronic address:
    Glycosylation is an important posttranslational modification, which regulates a number of critical biological processes including cell-cell recognition, signal transduction and disease progression. Probing the glycosylation status on a specific protein of interest enables an in-depth understanding of the role of glycosylation on protein structure and function. However, methods for monitoring protein-specific glycosylation are largely lacking. Read More

    A quantitative method for analyzing glycome profiles of plant cell walls.
    Carbohydr Res 2017 Aug 19;448:128-135. Epub 2017 Jun 19.
    Daniel B. Warnell School of Forestry and Natural Resources, University of Georgia, Athens, GA, USA.
    Glycome profiling allows for the characterization of plant cell wall ultrastructure via sequential extractions and subsequent detection of specific epitopes with a suite of glycan-specific monoclonal antibodies (mAbs). The data are often viewed as the amount of materials recovered and coinciding colored heatmaps of mAb binding are generated. Interpretation of these data can be considered qualitative in nature as it depends on detecting subtle visual differences in antibody binding strength. Read More

    Role of the triple solute/ion/water interactions on the saccharide hydration: A volumetric approach.
    Carbohydr Res 2017 Aug 20;448:118-127. Epub 2017 Jun 20.
    Laboratoire de Génie Chimique, Université de Toulouse, CNRS, INPT, UPS, Toulouse, France.
    The aim of this study is to further the understanding of the mechanisms that govern the hydration behavior of neutral solutes, with respect to the ions' properties that are present in a solution. For that, a systematic volumetric study of saccharides (xylose, glucose and sucrose), in the presence of various electrolytes (LiCl, NaCl, KCl, Na2SO4, K2SO4, CaCl2, MgCl2, MgSO4) has been carried out with density measurements at 298.15 K. Read More

    Structure of the LPS O-chain from Fusobacterium nucleatum strain 12230.
    Carbohydr Res 2017 Aug 16;448:115-117. Epub 2017 Jun 16.
    Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON, K1A 0R6, Canada.
    Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. It was also found in colorectal cancer tissues and is linked with pregnancy complications, including pre-term and still births. Cell surface structures of the bacterium could be implicated in pathogenesis. Read More

    Structure and gene cluster of the O-antigen of Enterobacter cloacae C4115.
    Carbohydr Res 2017 Aug 3;448:110-114. Epub 2017 Jun 3.
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation.
    An O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Enterobacter cloacae C4115 and studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the linear pentasaccharide repeating unit of the O-polysaccharide was established: →2)-α-l-Rhap-(1 → 2)-α-l-Rhap-(1 → 2)-α-l-Rhap-(1 → 2)-α-d-Galp-(1 → 3)-α-d-FucpNAc-(1→ The O-antigen gene cluster of E. cloacae C4115 was sequenced. Read More

    Synthesis of S-linked trisaccharide glycal of derhodinosylurdamycin A: Discovery of alkyl thiocyanate as an efficient electrophile for stereoselective sulfenylation of 2-deoxy glycosyl lithium.
    Carbohydr Res 2017 Aug 15;448:103-109. Epub 2017 Jun 15.
    Department of Chemistry and Biochemistry, School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606, United States. Electronic address:
    Stereoselective synthesis of S-linked trisaccharide glycal of angucycline antitumor antibiotic derhodinosylurdamycin A is described. The synthesis has been accomplished employing our previously reported umpolung S-glycosylation strategy - stereoselective sulfenylation of 2-deoxy glycosyl lithium. It was found that sugar-derived thiocyanate was a better electrophile than corresponding asymmetric disulfide in this type of stereoselective sulfenylation. Read More

    Structural characterization of the immunostimulatory exopolysaccharide produced by Leuconostoc mesenteroides strain NTM048.
    Carbohydr Res 2017 Aug 15;448:95-102. Epub 2017 Jun 15.
    Nitto Pharmaceutical Industries, Ltd., Kamiueno, Muko, Kyoto 617-0006, Japan.
    The exopolysaccharide (EPS) produced by probiotic Leuconostoc mesenteroides subsp. mesenteroides strain NTM048 has been reported to be an immunostimulant that enhances mucosal IgA production. In this study, we found that intranasal administration of mice with the EPS and an antigen (ovalbumin) resulted in secretion of antigen-specific IgA and IgG in the airway mucosa and the serum, suggesting that the EPS has the adjuvant activity for use with mucosal vaccination. Read More

    Structural characterization of wall and lipidated polysaccharides from Clostridium perfringens ATCC 13124.
    Carbohydr Res 2017 Aug 15;448:88-94. Epub 2017 Jun 15.
    National Research Council of Canada, Vaccine Program, Human Health Therapeutics, Ottawa Canada, K1A OR6.
    Cell surface polysaccharides produced by C. perfringens ATCC 13124 were analyzed using NMR, chemical and immunological methods. Two distinct polymers were identified. Read More

    Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives.
    Carbohydr Res 2017 Aug 12;448:79-87. Epub 2017 Jun 12.
    Department of Organic Chemistry, Gdańsk University of Technology, Gdańsk, Poland.
    6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts. GlcN6S and ADGS at micromolar concentrations inhibited glucosamine-6-phosphate (GlcN6P) synthase of microbial origin. The former was also inhibitory towards fungal GlcN6P N-acetyl transferase, but at millimolar concentrations. Read More

    Rumpictuside A: Unusual 9,10-anthraquinone glucoside from Rumex pictus Forssk.
    Carbohydr Res 2017 Aug 9;448:74-78. Epub 2017 Jun 9.
    Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan.
    A new 8-ionized hydroxylated 9,10-anthraquinone namely, 1-hydroxy-3-methyl-9,10-anthraquinone-6-O-β-D-glucopyranoside-8-olate (Rumpictuside A, 1) along with five known flavonoids, apigenin 7-O-β-D-glucoside (2), vitexin (3), quercetin 3-O-β-D-glucouronide (4), orientin (5), and isorientin (6) were isolated from Rumex pictus. The structures of isolated compounds were identified by the extensive spectroscopic techniques such as, UV, FT-IR, 1D, 2D NMR and HR-FAB-ESI-MS. The ionized hydroxyl group in the new anthraquinone (1) was rarely found for anthraquinone glycosides isolated from natural sources. Read More

    Biochemical and structural characterization of Penicillium purpurogenum α-D galactosidase: Binding of galactose to an alternative pocket may explain enzyme inhibition.
    Carbohydr Res 2017 Aug 9;448:57-66. Epub 2017 Jun 9.
    Laboratorio de Fisiología Vegetal y Genética Molecular, Instituto de Ciencias Biológicas, Universidad de Talca, Avenida Lircay s/n, Talca, Chile. Electronic address:
    The fungus Penicillium purpurogenum degrades plant cell walls by the action of cellulolytic, xylanolytic and pectinolytic enzymes. The α-D-galactosidase is one of the enzymes which may act on pectin degradation. This enzyme has several biotechnological and medical applications. Read More

    Oxidation of 3,5-di-C-(per-O-acetylglucopyranosyl)phloroacetophenone in the synthesis of hydroxysafflor yellow A.
    Carbohydr Res 2017 Aug 13;448:52-56. Epub 2017 May 13.
    Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan. Electronic address:
    In the synthesis of the main yellow pigment hydroxysafflor yellow A (HSYA), that is present in safflower petals, the key compound 4-(S)-2-acetyl-4,6-di-C-(per-O-acetyl-β-D-glucosyl)-3,4-dihydroxy-5-methoxycyclohexa-2,5-dienone (11b) was diastereoselectively synthesized in an overall yield of 18% from di-C-β-D-glucosylphloroacetophenone per-O-acetate (8). Read More

    Studies on the O-specific polysaccharide of the lipopolysaccharide from the Pseudomonas mediterranea strain C5P1rad1, a bacterium pathogenic of tomato and chrysanthemum.
    Carbohydr Res 2017 Aug 1;448:48-51. Epub 2017 Jun 1.
    Dipartimento di Scienze Chimiche, Universitá di Napoli Federico II, I-80126 Naples, Italy. Electronic address:
    An O-specific polysaccharide (OPS) was isolated from the lipopolysaccharide of Pseudomonas mediterranea strain C5P1rad1, the causal agents of tomato pith necrosis and Chrysanthemum stem rot, and studied by one- and two-dimensional (1)H and (13)C NMR spectroscopy. The following structure of the trisaccharide repeating unit of the OPS was established, which, to our knowledge, is unique among the known bacterial polysaccharide structures: →4)-β-d-ManpNAc3NAcA-(1 → 4)-β-d-ManpNAc3NAcA-(1 → 3)-α-d-QuipNAc4NAc-(1→ where QuiNAc4NAc and ManNAc3NAcA indicate 2,4-diacetamido-2,4,6-trideoxyglucose and 2,3-diacetamido-2,3-dideoxymannuronic acid, respectively. Pre-treatment of leaves with LPS or OPS preparations at 250 and 50 μg mL(-1) did not inhibit development of a hypersensitivity reaction induced by P. Read More

    Synthesis of a glucosylated α-S-galactosylceramide as potential immunostimulant.
    Carbohydr Res 2017 Aug 1;448:43-47. Epub 2017 Jun 1.
    Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland. Electronic address:
    Synthesis of a glucosylated α-S-galactosylceramide (1), a potential immunostimulant, was achieved starting from D-galactose. Both O- and S-glycosidic linkages were constructed in highly stereoselective way, and the synthetic strategy could be extended to the synthesis of other α-S-GalCer analogues. Read More

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