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    10009 results match your criteria Carbohydrate research[Journal]

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    Synthesis of sulfamide analogues of deoxthymidine monophosphate as potential inhibitors of mycobacterial cell wall biosynthesis.
    Carbohydr Res 2018 Jan 11;457:32-40. Epub 2018 Jan 11.
    Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, 8140, New Zealand; Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch, 8140, New Zealand. Electronic address:
    The recently discovered enzyme Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt), which catalyses the phosphorylation of deoxythymidine monophosphate (dTMP) to give deoxythymidine diphosphate (dTDP), is indispensable for the growth and survival of M. tuberculosis as it plays an essential role in DNA synthesis. Inhibition of TMPKmt is an attractive avenue for the development of novel anti-tuberculosis agents. Read More

    Structure elucidation of the O-specific polysaccharide by NMR spectroscopy and selective cleavage and genetic characterization of the O-antigen of Escherichia albertii O5.
    Carbohydr Res 2018 Jan 3;457:25-31. Epub 2018 Jan 3.
    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, Zhejiang Province, China.
    The O-specific polysaccharide (O-antigen) was obtained by mild acid degradation of the lipopolysaccharide of Escherichia albertii O5 (strain T150248) and studied by sugar analysis, selective cleavages of glycosidic linkages, and 1D and 2D 1H and 13C NMR spectroscopy. Partial solvolysis with anh (anhydrous) CF3CO2H and hydrolysis with 0.05 M CF3CO2H cleaved predominantly the glycosidic linkage of β-GalpNAc or β-Galf, respectively, whereas the linkages of α-GlcpNAc and β-Galp were stable. Read More

    Chondroitin sulfate-stabilized silver nanoparticles: Improved synthesis and their catalytic, antimicrobial, and biocompatible activities.
    Carbohydr Res 2017 Dec 14;457:14-24. Epub 2017 Dec 14.
    Institute of Preventive Medicine, National Defense Medical Center, New Taipei City 23742, Taiwan. Electronic address:
    Herein, we describe an improved procedure for the green synthesis of chondroitin sulfate stabilized silver nanoparticles (ChS-AgNPs). Glucose was used as a reducing agent under alkaline conditions to obtain a small particle size (<10 nm), and the reduction was complete within one hour at room temperature. The concentration of NaOH affected the reaction rate, formation yield, and particle size of ChS-AgNPs. Read More

    Structural analysis of the O-polysaccharide from the lipopolysaccharide of Pseudomonas putida BIM B-1100.
    Carbohydr Res 2017 Dec 25;457:8-13. Epub 2017 Dec 25.
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation.
    Two specific polysaccharides, together with an →4)-α-d-Glcp-(1→ glucan (bacterial glycogen), were obtained from a lipopolysaccharide preparation isolated from the bacterium Pseudomonas putida BIM B-1100 by phenol/water extraction. The following structures of the polysaccharides were established by composition analysis, Smith degradation, ESI-MS, and 1D and 2D NMR spectroscopy. Read More

    Cloning, purification and biochemical characterization of two β-N-acetylhexosaminidases from the mucin-degrading gut bacterium Akkermansia muciniphila.
    Carbohydr Res 2017 Dec 23;457:1-7. Epub 2017 Dec 23.
    Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, 1 Weigang, Nanjing 210095, China. Electronic address:
    Two genes encoding the β-N-acetylhexosaminidases Am2301 and Am2446 were cloned successfully from the mucin-degrading bacterium Akkermansia muciniphila. The recombinant enzymes with molecular masses of 61 kDa and 78 kDa were isolated and biochemically characterised. The optimum temperature of both enzymes was 37 °C, and the optimum pH was determined to be pH 5. Read More

    Reaction specificity of keratanase II in the transglycosylation using the sugar oxazolines having keratan sulfate repeating units.
    Carbohydr Res 2017 Dec 15;456:61-68. Epub 2017 Dec 15.
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan. Electronic address:
    The reaction specificity of the transglycosylation catalyzed by keratanase II from Bacillus circulans KsT202 (KSase II) was studied by using the oxazoline derivatives having keratan sulfate repeating units. The addition of 10% organic cosolvent reduced the activity for the enzymatic transglycosylation. The oxazoline derivative of 6-O-sulfonato-N-acetyllactosamine (su-LacNAc) was processively oligomerized to the corresponding hexamer or longer by the enzyme. Read More

    Bisecting GlcNAc restricts conformations of branches in model N-glycans with GlcNAc termini.
    Carbohydr Res 2017 Dec 14;456:53-60. Epub 2017 Dec 14.
    Structural Glycobiology Team, Systems Glycobiology Research Group, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, RIKEN Global Research Cluster, Wako, Saitama, 351-0198, Japan. Electronic address:
    Bisected N-glycans play significant roles in tumor migration and Alzheimer's disease through modulating the action and localization of their carrier proteins. Such biological functions are often discussed in terms of the conformation of the attached N-glycans with or without bisecting GlcNAc. To obtain insights into the effects of bisecting GlcNAc on glycan conformation, a systematic NMR structural analysis was performed on two pairs of synthetic N-glycans, with and without bisecting GlcNAc. Read More

    Synthesis of tetracyclic azasugars fused benzo[e][1,3]thiazin-4-one by the tandem Staudinger/aza-Wittig/cyclization and their HIV-RT inhibitory activity.
    Carbohydr Res 2017 Dec 15;456:45-52. Epub 2017 Dec 15.
    Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China. Electronic address:
    Azasugar aldehydes 6a and 6b containing azido groups were prepared from D-mannose. Three novel tetracyclic azasugars fused benzo[e][1,3]thiazin-4-one 9a-1, 9a-2 and 9a-3 were conveniently synthesized from 6a by the tandem intramolecular Staudinger/aza-Wittig/cyclization reaction under microwave radiation. Two unexpected elimination compounds 8b-1 and 8b-2 were achieved as the main products from 6b in the same processes. Read More

    Arabinofuranose 1,2,5-orthobenzoate as a single precursor of linear α(1 → 5)-linked oligoarabinofuranosides.
    Carbohydr Res 2017 Dec 8;456:35-44. Epub 2017 Dec 8.
    N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991 Moscow, Russian Federation. Electronic address:
    Selectively protected mono-, di- and trisaccharide thioglycoside building blocks with unprotected primary hydroxy group at the non-reducing end, available in only one step from 3-O-benzoyl β-d-arabinofuranose 1,2,5-orthobenzoate, were used in the synthesis of linear α(1 → 5)-linked oligoarabinofuranosides up to octasaccharide. The obtained oligosaccharides contain 4-(2-chloroethoxy)phenyl (CEP) or 4-(2-azidoethoxy)phenyl (AEP) pre-spacer aglycons that allow preparation of neoglycoconjugates. Read More

    A concise route to access C-glycosidic tetrazolyl analogues of Kdo as bioisosteres.
    Carbohydr Res 2017 Dec 14;456:30-34. Epub 2017 Dec 14.
    University of Vienna, Institute of Organic Chemistry, Währinger Straße 38, A-1090 Vienna, Austria.
    Ulosonic acids are an important class of carbohydrates, including well-known representatives as 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-d-glycero-d-galacto-non-2-ulosonic acid (Kdn) and N-Acetylneuraminic acid (Neu5Ac). As part of the lipopolysaccharides (LPS) and capsular polysaccharides (CPS, K-antigen), these carbohydrates can be found on the surfaces of, both, Gram-positive and Gram-negative bacteria. We developed a synthetic approach to access tetrazole-derivatives of these compounds. Read More

    Conjugation of carbohydrates to proteins using di(triethylene glycol monomethyl ether) squaric acid ester revisited.
    Carbohydr Res 2017 Nov 7;456:24-29. Epub 2017 Nov 7.
    NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA. Electronic address:
    Properties of di(triethylene glycol monomethyl ether) squarate relevant to conjugation of carbohydrates to proteins have been reinvestigated and compared with those of dimethyl squarate. It is concluded that the commercially available, crystalline dimethyl squarate remains the most convenient and efficient reagent for conjugation of amine-containing carbohydrates to proteins by a two-step or one-pot conjugation protocol. Read More

    Structural and immunological characterization of a glycoconjugate based on the delipidated lipopolysaccharide from a nontypeable Helicobacter pylori strain PJ1 containing an extended d-glycero-d-manno-heptan.
    Carbohydr Res 2017 Dec 7;456:19-23. Epub 2017 Dec 7.
    Vaccines and Immunotherapeutics Program, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada. Electronic address:
    Structural characterization of the lipopolysaccharide (LPS) from a nontypeable Helicobacter pylori strain PJ1 and two corresponding mutants, PJ1 HP1283:cam and PJ1 HP1284:cam, was performed using a combination of NMR and mass spectrometric techniques. It resulted in the core structure that differed significantly from the one proposed previously. Overall architecture of PJ1 LPS was found to be consistent with a structural model described for several other H. Read More

    Synthesis of the repeating unit of O-specific polysaccharide isolated from the water-borne bacteria Aeromonas bestiarum 207.
    Carbohydr Res 2017 Nov 21;456:10-18. Epub 2017 Nov 21.
    Department of Applied Chemistry, China Agricultural University, Beijing 100193, PR China. Electronic address:
    Aeromonas bestiarum 207 is a bacterial pathogen with severe impact on aquaculture. In a recent study, the structure of OPS antigens from Aeromonas bestiarum was identified as pentasaccharide repeating units. Synthesis of the pentasaccharide repeating unit and its derivative are reported. Read More

    A highly regular fucan sulfate from the sea cucumber Stichopus horrens.
    Carbohydr Res 2017 Dec 7;456:5-9. Epub 2017 Dec 7.
    N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia. Electronic address:
    A highly regular fucan sulfate SHFS was isolated from the sea cucumber Stichopus horrens by extraction of the body walls in the presence of papain followed by ion-exchange and gel permeation chromatography. SHFS had MW of about 140 kDa and contained fucose and sulfate in the molar ratio of about 1:1. Chemical and NMR spectroscopic methods were applied for the structural characterization of the polysaccharide. Read More

    Structure and genetics of the O-specific polysaccharide of Escherichia coli O27.
    Carbohydr Res 2017 Dec 2;456:1-4. Epub 2017 Dec 2.
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation.
    The O-specific polysaccharide (O-antigen) is a part of the lipopolysaccharide on the cell surface of Gram-negative bacteria. The O-polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O27 and studied by sugar analysis and Smith degradation along with 1H and 13C NMR spectroscopy. The following structure of the branched hexasaccharide repeating unit was established, which is unique among known structures of bacterial polysaccharides:where GlcA is non-stoichiometrically O-acetylated at position 3 (∼22%) or 4 (∼37%). Read More

    Hafnium(IV) triflate as a potent catalyst for selective 1-O-deacetylation of peracetylated saccharides.
    Carbohydr Res 2018 Jan 5;455:114-118. Epub 2017 Dec 5.
    Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, PR China. Electronic address:
    An efficient method for selective anomeric deacetylation of peracetylated mono-, di-, and trisaccharides has been developed by using 2 mol% Hf(OTf)4 as catalyst in acetonitrile. Employment of ultrasonic irradiation could significantly accelerate the reaction rate. Mechanistic study confirmed the hydrolysis nature of this reaction, and NMR experimental data suggested that multiple peracetylated saccharide molecules may ligate to Hf(IV) cation primarily via the anomeric acetate to promote its specific hydrolysis. Read More

    Penicillium purpurogenum produces a novel endo-1,5-arabinanase, active on debranched arabinan, short arabinooligosaccharides and on the artificial substrate p-nitrophenyl arabinofuranoside.
    Carbohydr Res 2018 Jan 26;455:106-113. Epub 2017 Nov 26.
    Departamento de Ciencias Biológicas, Universidad Andrés Bello, República 217, Santiago, Chile. Electronic address:
    Penicillium purpurogenum secretes numerous lignocellulose-degrading enzymes, including four arabinofuranosidases and an exo-arabinanase. In this work, the biochemical properties of an endo-arabinanase (ABN1) are presented. A gene, coding for a potential ABN was mined from the genome. Read More

    Developing cellulosic waste products as platform chemicals: protecting group chemistry of α-glucoisosaccharinic acid.
    Carbohydr Res 2018 Jan 26;455:97-105. Epub 2017 Nov 26.
    Department of Chemical Sciences, School of Applied Sciences, University of Huddersfield, Queensgate Huddersfield, HD1 3DH, United Kingdom. Electronic address:
    Alpha and beta-glucoisosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) which are produced when cellulosic materials are treated with aqueous alkali are potentially valuable platform chemicals. Their highly functionalised carbon skeleton, with fixed chirality at C-2 and C-4, makes them ideal starting materials for use in synthesis. In order to assess the potential of these saccharinic acids as platform chemicals we have explored the protecting group chemistry of the lactone form of alpha-glucoisosaccharinic acid (α-GISAL). Read More

    Chemo-enzymatic synthesis of the glucagon containing N-linked oligosaccharide and its characterization.
    Carbohydr Res 2018 Jan 13;455:92-96. Epub 2017 Nov 13.
    Division of Integrated Life Science, Graduate School of Biostudies, Kyoto University, Kyoto, 606-8501, Japan; Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Nonoich, Ishikawa, 921-8836, Japan. Electronic address:
    The chemo-enzymatic synthesis of an artificially N-glycosylated derivative of glucagon, a peptide hormone that regulates the blood sugar level, is described. We synthesized the glycosylated glucagon by chemical synthesis of an N-acetylglucosaminyl peptide and enzymatic transfer of an oligosaccharide using the transglycosylation activity of the glycosynthase-like mutant of Mucor hiemalis endo-β-N-acetylglucosaminidase (Endo-M) and sialo-oligosaccharide oxazoline as a donor substrate. The sialo-oligosaccharide-attached glucagon synthesized showed high resistance against protease degradation and stimulated the release of glucose from mouse hepatocytes when added to cells. Read More

    DIDMH in combination with triflic acid - A new promoter system for thioglycoside glycosyl donors.
    Carbohydr Res 2018 Jan 21;455:86-91. Epub 2017 Nov 21.
    Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark. Electronic address:
    We have explored the possibility of using 1,3-diiodo-5,5-dimethylhydantoin (DIDMH) as an alternative to N-iodosuccinimide (NIS) for activation of glycosyl donors of the thioglycoside type in various glycosylation reactions. DIDMH was found to match NIS when it comes to the capability to activate thioglycosides and provide glycosylation products in good yields. Notably, with the two equivalents of reactive iodonium ions per molecule of DIDMH less mass needs to be added making this activator a more atom economically alternative to NIS. Read More

    Сonformational study of persulfated propyl glucuronide.
    Carbohydr Res 2018 Jan 17;455:81-85. Epub 2017 Nov 17.
    Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
    Glucuronic acid is an important constituting block of biologically active glycosaminoglycans where it can be present in non-sulfated, mono-sulfated and di-sulfated forms. Despite that some investigators reported previously that the exhaustively sulfated glucuronic acid moiety was characterized with unusual 1H-1H coupling constants and some times chemical shifts, these were just qualitative studies in which their authors suggested that the mentioned deviations in NMR spectra might mean complete inversion of the normal D-pyranoside chair conformation 4C1 to 1C4. Herein we outline a detailed conformational investigation showing that the distortion in the pyranoside ring of the persulfated glucuronic acid cannot be described simply with 4C1↔1C4 inversion. Read More

    A combined variable temperature 600 MHz NMR/MD study of the calcium release agent cyclic adenosine diphosphate ribose (cADPR): Structure, conformational analysis, and thermodynamics of the conformational equilibria.
    Carbohydr Res 2018 Jan 15;455:71-80. Epub 2017 Nov 15.
    Department of Chemistry, St. John's University, 8000 Utopia Parkway, Queens, NY 11439, USA. Electronic address:
    A combined variable temperature 600 MHz NMR/molecular dynamics study of the Ca2+-release agent cyclic adenosine 5'-diphosphate ribose (cADPR) was conducted. In addition to elucidating the major and minor orientations of the conformationally flexible furanose rings, γ- (C4'-C5'), and β- (C5'-O5') bonds, the thermodynamics (ΔHo, ΔSo) associated with each of these conformational equilibria were determined. Both furanose rings were biased towards a south conformation (64-74%) and both β-bonds heavily favored trans conformations. Read More

    Pyranose ring puckering in aldopentoses, ketohexoses and deoxyaldohexoses. A molecular dynamics study.
    Carbohydr Res 2018 Jan 21;455:62-70. Epub 2017 Nov 21.
    Jerzy Haber Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, ul. Niezapominajek 8, 30-239, Cracow, Poland. Electronic address:
    Conformation of monosaccharides, including the ring shape, has for years been the subject of intensive research. Although d-aldohexopyranoses are the most extensively studied pyranoses, there also exist other groups of saccharides that contain analogous chemical system of the six-membered ring. Here we describe in details the results of the molecular dynamics-based conformational analysis concerning a series of pyranoses, namely: d-aldopentoses, d-ketohexoses as well as deoxy- (d-quinovose, l-fucose, l-rhamnose) and dideoxy- (abequose, paratose, tyvelose, digitoxose) derivatives of aldohexoses. Read More

    Role of 6-O-α-maltosyl-β-cyclodextrin in lysosomal cholesterol deprivation in Npc1-deficient Chinese hamster ovary cells.
    Carbohydr Res 2018 Jan 10;455:54-61. Epub 2017 Nov 10.
    School of Pharmacy and Pharmaceutical Sciences, Institute Biosciences, Mukogawa Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan.
    We aimed to investigate whether 6-O-α-maltosyl-β-cyclodextrin (Mal-βCD) is incorporated into cells and lysosomes during the release of unesterified cholesterol in Npc1-deficient Chinese hamster ovary (CHO) cells (Npc1 KO cells) and CHO-JP17 cells (JP17 cells). Internalization of Mal-βCD in cells and lysosomes and extracellular release of lysosomal unesterified cholesterol were demonstrated by LC/MS/MS and LC/MS, respectively. Internalization of Mal-βCD was greater in Npc1 KO cells than in JP17 cells. Read More

    Synthesis of aromatic and indole alpha-glucosinolates.
    Carbohydr Res 2018 Jan 20;455:45-53. Epub 2017 Nov 20.
    Department of Chemistry and Physics, La Trobe University, Victoria 3086, Australia.
    Aromatic and indole glucosinolates are important members of the glucosinolate family of compounds du to their potential medicinal properties. They are known to exert antioxidant and anti-carcinogenic activity either by the natural products themselves, or their metabolic products including indole-3-carbinol and isothiocyanates. Natural glucosinolates are all β-glucosinolates; however, α-glucosinolates are also promising compounds for medicinal applications and hence have to be produced synthetically for any bio-activity studies. Read More

    The Shewanella woodyi galactokinase pool phosphorylates glucose at the 6-position.
    Carbohydr Res 2018 Jan 31;455:39-44. Epub 2017 Oct 31.
    Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, 1 Weigang, Nanjing 210095, China. Electronic address:
    Galactokinases are a class of enzymes which belong to the GHMP (galactokinase, homoserine kinase, mevalonate kinase, and phosphomevalonate kinase) superfamily and catalyse the phosphorylation of galactose in the first step of the Leloir pathway. Here we report the discovery of three enzymes from Shewanella woodyi which have been classified as galactokinases based on sequence similarity. However, each of these enzymes show little to no significant activity towards galactose and instead exhibit a strong preference for glucose. Read More

    Microfluidic reactor for lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives and their antimicrobial activity research.
    Carbohydr Res 2018 Jan 21;455:32-38. Epub 2017 Nov 21.
    College of Pharmaceutical Science, ZheJiang University of Technology, Hangzhou, 310014, China; Department of Environmental Science and Technology, ZheJiangA&F University, Hangzhou, 311300, China.
    Lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives was performed by Lipase TL IM from Thermomyces lanuginosus in a continuous-flow microreactor and then their antimicrobial activity was studied. It appears that neohesperidin, neohesperidin dihydrochalcone with primary OH on the sugar part is the most reactive substrate. Various reaction parameters were investigated including substrate molar ratio, reaction time and temperature. Read More

    A concise synthesis of rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages by iterative α-glycosylation using disaccharide building blocks.
    Carbohydr Res 2018 Jan 14;455:23-31. Epub 2017 Nov 14.
    Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu 501-1193, Japan; Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu, Gifu 501-1193, Japan.
    A concise synthetic route to rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages is reported. This synthesis was achieved by iterative α-glycosylation using disaccharide building blocks and through orthogonal coupling between thioglycosides of L-rhamnose. To investigate the detailed structure-activity relationship of rhamnan sulfate from Monostroma nitidum against herpes simplex virus type 2, the synthesized oligosaccharides, bearing different orthogonal protecting groups (i. Read More

    Synthesis of 3-aminopropyl β-(1 → 6)-d-glucotetraoside and its biotinylated derivative.
    Carbohydr Res 2018 Jan 6;455:18-22. Epub 2017 Nov 6.
    Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia. Electronic address:
    3-Aminopropyl β-(1 → 6)-d-glucotetraoside has been synthesized from 3-benzyloxycarbonylaminopropanol and 6-O-acetyl-2,3,4-tri-O-benzoyl-d-glucopyranosyl trichloroacetimidate by successive attachment of one monosaccharide unit in total yield of 22%. Free aminopropyl glycoside was converted into a biotin derivative that can be used for controlled immobilization of the oligosaccharide on streptavidin-coated ELISA plates and for tracing carbohydrate binding molecules. Read More

    Isolation and characterisation of an unexpected byproduct in the regioselective butane diacetal protection of α-methyl galactopyranoside.
    Carbohydr Res 2018 Jan 6;455:14-17. Epub 2017 Nov 6.
    Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK. Electronic address:
    The regioselective protection of both methyl galactopyranoside anomers at the 2 and 3-positions as the butane diacetal (BDA) is well known. Here we describe the formation of an unexpected byproduct, which mainly occurs when α-methyl galactopyranoside is reacted with 2,3-butanedione under BF3•OEt2 catalysis. The structure of the byproduct, which did not arise from anomerisation to the β-anomer or from BDA formation at the galactopyranoside 3,4-positions, was elucidated by NMR and X-ray crystallographic analysis, and proved to be the expected BDA protected galactopyranoside, but in which the stereochemistry of both its BDA acetal centres are inverted. Read More

    Tandem mass spectrometry of fucoidan-derived fragments, labeled with heavy-oxygen.
    Carbohydr Res 2018 Jan 4;455:10-13. Epub 2017 Nov 4.
    G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Stoletiya Vladivostoka Prosp. 159/2, 690022 Vladivostok, Russian Federation.
    A procedure for the partial depolymerization of sulfated fucans and selective labeling with 18O was developed. A tandem electrospray ionization mass spectrometry (ESI MS/MS) was applied for the direct analysis of mixtures of structurally-different oligosaccharides, derived from the fucoidans of known structure. The presence of label allowed unambiguous distinguishing between the fragment ions of 0,2X0-type at m/z 287 and 2,4A-type at m/z 285, since 18O at the reducing end gave +2 mass shifting. Read More

    Concise synthesis of 2,7-anhydrosialic acid derivatives and its application.
    Carbohydr Res 2017 Dec 19;453-454:44-53. Epub 2017 Oct 19.
    Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan; Taiwan International Graduate Program (TIGP), Sustainable Chemical Science and Technology (SCST), Academia Sinica, Taipei 115, Taiwan. Electronic address:
    In N-acetylneuraminic acid, apart from O9 and O8, a possible glycosylation site is the O4 position. For example, gangliosides HLG-2 and HPG-7 are considered to be potential lead compounds for carbohydrate-based drug development to treat neural disorders. However, the construction of their α(1 → 4) fucosyl sialic acid and α(2 → 4) linkages between sialic acids is difficult because of the regioselectivity problem. Read More

    Effect of sucralose on the enzyme kinetics of invertase using real-time NMR spectroscopy and progress curve analysis.
    Carbohydr Res 2018 Jan 31;455:5-9. Epub 2017 Oct 31.
    Department of Chemistry, California State University, Fresno CA 93740, United States; Department of Pathology and Laboratory Medicine, School of Medicine, University of California, Davis CA 95616, United States. Electronic address:
    Sucralose, a derivative of sucrose, is widely used in noncaloric artificial sweeteners (NAS). Contrary to the belief that sucralose is physiologically inert and a healthy alternative sweetener to natural sugar, emerging studies indicate that sucralose alters the host metabolism as well as the composition of the microbiome. In this manuscript, we use real-time nuclear magnetic resonance (NMR) spectroscopy to demonstrate that sucralose alters the enzymatic conversion of sucrose to glucose and fructose. Read More

    Supramolecular glycorhodamine-polymer dot ensembles for the homogeneous, fluorogenic analysis of lectins.
    Carbohydr Res 2018 Jan 1;455:1-4. Epub 2017 Nov 1.
    Key Laboratory for Advanced Materials & Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd., Shanghai 200237, China. Electronic address:
    We have developed a new series of glycoprobe-polymer dot ensembles for the fluorogenic, homogeneous detection of lectins. Electrostatic self-assembly between positively charged rhodamine-based glycosides and negatively charged poly(3-hexylthiophene-2,5-diyl)/poly(styrene-co-maleic anhydride) polymer dots produces the ensembles with a quenched fluorescence. Fluorescence spectroscopy showed that the ensembles exhibited a concentration-dependent fluorescence enhancement with selective lectins over a range of unselective lectins and proteins. Read More

    Mannosylcalix[n]arenes as multivalent ligands for DC-SIGN.
    Carbohydr Res 2017 Dec 31;453-454:36-43. Epub 2017 Oct 31.
    Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Università di Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy. Electronic address:
    DC-SIGN is a receptor protruded from the membrane of immature dendritic cells (DCs) that participates in the activation of the immune response through the recognition of pathogen-associated molecular patterns (PAMPs). On the other hand, HIV exploits the interaction between high-mannose structures of its envelope glycoprotein gp120 and DC-SIGN to be transported towards and infect T-cells. DC-SIGN is involved in the recognition process in the form of a tetramer and the multiple exposition of carbohydrate recognition sites (CRSs) is amplified by the formation on the DCs membrane of patches of tetramers. Read More

    Properties of two fungal endo-β-1,3-galactanases and their synergistic action with an exo-β-1,3-galactanase in degrading arabinogalactan-proteins.
    Carbohydr Res 2017 Dec 25;453-454:26-35. Epub 2017 Oct 25.
    Division of Life Science, Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570, Japan; Institute for Environmental Science and Technology, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570, Japan. Electronic address:
    Arabinogalactan-proteins (AGPs) are plant proteoglycans, which are widely encountered in the plant kingdom, usually localized on the cell surface. The carbohydrate moieties of AGPs consist of β-1,3-galactan main chains and β-1,6-galactan side chains, to which other auxiliary sugars are attached. To date, FvEn3GAL isolated from Flammulina velutipes is the sole β-1,3-galactanase acting on β-1,3-galactan in an endo-manner. Read More

    Synthesis of P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate for the investigation of biosynthesis of O-antigenic polysaccharides in Pseudomonas aeruginosa and Escherichia coli O104.
    Carbohydr Res 2017 Dec 4;453-454:19-25. Epub 2017 Nov 4.
    Department of Biomedical and Molecular Sciences, Queen's University, Kingston, Canada.
    Two new phenoxyundecyl diphosphate sugars were synthesized for the first time: P1-(11-phenoxyundecyl)-P2- (2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate to study the third step of biosynthesis of the repeating units of O-antigenic polysaccharides in Pseudomonas aeruginosa and E.coli O104 respectively. Read More

    Synthesis of substrate analogues as potential inhibitors for Mycobacterium tuberculosis enzyme MshC.
    Carbohydr Res 2017 Dec 3;453-454:10-18. Epub 2017 Nov 3.
    Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States. Electronic address:
    Mycothiol cysteine ligase (MshC) is a key enzyme in the mycothiol (MSH) biosynthesis and a promising target for developing new anti-mycobacterial compounds. Herein, we report on the synthesis of substrate analogues, as potential inhibitors, for the MshC enzyme. The target molecules were synthesized employing a Schmidt glycosylation strategy using an enantiomerically pure inositol acceptor and 2-deoxy trichloroacetimidate glycosyl donors with glycosylation yields greater than 70% and overall yields >5%. Read More

    Overview on the antiviral activities and mechanisms of marine polysaccharides from seaweeds.
    Carbohydr Res 2017 Dec 31;453-454:1-9. Epub 2017 Oct 31.
    Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Lihu Avenue1800, Wuxi 214122, China. Electronic address:
    Marine polysaccharides are attracting increasing attention in medical and pharmaceutical development because of their important biological properties. The seaweed polysaccharides have now become a rich resource of potential antiviral drugs due to their antiviral activities against various viruses. The structural diversity and complexity of marine polysaccharides and their derivatives contribute to their antiviral activities in different phases of many different viral infection processes. Read More

    Monitoring of reactions catalyzed by lytic polysaccharide monooxygenases using highly-sensitive fluorimetric assay of the oxygen consumption rate.
    Carbohydr Res 2017 Nov 24;452:156-161. Epub 2017 Oct 24.
    Department of Chemistry, M. V. Lomonosov Moscow State University, Vorobyovy Gory 1/11, Moscow 119991, Russia; Federal Research Centre "Fundamentals of Biotechnology", Russian Academy of Sciences, Leninsky Pr. 33, Moscow 119071, Russia.
    Lytic polysaccharide monooxygenases (LPMOs) are recently discovered enzymes that catalyze the oxidative deconstruction of polysaccharides. However fast and reliable methods of determination of LPMO activity still need to be developed, especially those based on the initial reaction rates. A method based on the oxygen consumption rate (OCR) measurements, using a Seahorse XFp Analyzer with highly-sensitive fluorimetric sensors, was applied for monitoring the oxidation of amorphous cellulose by three fungal LPMOs: recombinant enzymes from Thielavia terrestris (GH61E), Trichoderma reesei (Cel61A), and a native LPMO9A from Myceliophthora thermophila. Read More

    Acinetobacter baumannii K13 and K73 capsular polysaccharides differ only in K-unit side branches of novel non-2-ulosonic acids: di-N-acetylated forms of either acinetaminic acid or 8-epiacinetaminic acid.
    Carbohydr Res 2017 Nov 19;452:149-155. Epub 2017 Oct 19.
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
    Structures of capsular polysaccharides of Acinetobacter baumannii isolates carrying KL13 and KL73 gene clusters were established. The closely related KL73 and KL13 gene clusters differ only by one gene in the module responsible for synthesis of the non-2-ulosonic acids. The K13 and K73 polysaccharides differ only in a single side-chain sugar, which is either 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-altro- or -d-glycero-l-altro-non-2-ulosonic acid [di-N-acetylated forms of acinetaminic acid (Aci5Ac7Ac) or 8-epiacinetaminic acid (8eAci5Ac7Ac), respectively]. Read More

    Synthesis of a biotinylated keratan sulfate tetrasaccharide composed of dimeric Galβ1-4GlcNAc6Sβ.
    Carbohydr Res 2017 Nov 18;452:97-107. Epub 2017 Sep 18.
    Department of Regional Environment, Faculty of Regional Sciences, Tottori University, Tottori 680-8551, Japan; Department of Life and Environmental Agricultural Sciences, Faculty of Agriculture, Tottori University, Tottori 680-8553, Japan. Electronic address:
    We successfully synthesized the biotinylated keratan sulfate tetrasaccharide, Galβ1-4GlcNAc6Sβ1-3Galβ1-4GlcNAc6Sβ in a stereocontrolled manner. The suitably protected Galβ1-4GlcNPhth unit was converted to the corresponding donor and acceptor. Optimization in 2 + 2 coupling using AgOTf, CuBr2, and n-Bu4NBr in CH3NO2 at a low temperature afforded the desired tetrasaccharide that suppressed glycal formation. Read More

    Boronic acid-based chemical sensors for saccharides.
    Carbohydr Res 2017 Nov 20;452:129-148. Epub 2017 Oct 20.
    College of Chemistry, Beijing Normal University, Beijing 100875, China. Electronic address:
    During the past decades, the interaction between boronic acids-functionalized sensors and saccharides is of great interest in the frontier domain of the interdiscipline concerning both biology and chemistry. Various boronic acid-based sensing systems have been developed to detect saccharides and corresponding derivatives in vitro as well as in vivo, which embrace unimolecular sensors, two-component sensing ensembles, functional assemblies, and boronic acid-loaded nanomaterials or surfaces. New sensing strategies emerge in endlessly with excellent selectivity and sensitivity. Read More

    Improved isolation and characterization procedure of sialylglycopeptide from egg yolk powder.
    Carbohydr Res 2017 Nov 12;452:122-128. Epub 2017 Oct 12.
    Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA; Department of Chemistry, University of Georgia, Athens, GA 30602, USA; Chemical Biology and Drug Discovery, Utrecht University, 3584 CG Utrecht, The Netherlands; Utrecht Institute for Pharmaceutical Sciences, Utrecht University, 3584 CG Utrecht, The Netherlands; Bijvoet Center for Biomolecular Research, Utrecht University, 3584 CH Utrecht, The Netherlands. Electronic address:
    Sialylglycopeptide (SGP) is a complex bi-antennary N-glycan bearing a short peptide fragment that can be isolated from the yolk of hen eggs. This natural product has gained popularity as a starting material for the semi-synthesis of N-glycans. We have found that current isolation methods provide a glycopeptide contaminated with several related structures, one being a glycopeptide having a hexose directly attached to peptide backbone, most like through the hydroxyl containing side chain of the threonine moiety. Read More

    Regioselective glycosylation of novobiocin alters activity.
    Carbohydr Res 2017 Nov 22;452:116-121. Epub 2017 Oct 22.
    The School of Pharmacy, University College London, 29/39 Brunswick Square, London WC1N 1AX, UK. Electronic address:
    Glycosylation is a promising approach to overcome antimicrobial drug resistance. In this study, we investigated Koenigs-Knorr and phase transfer glycosylation on novobiocin. While the former only gave a 4'-OH product, the later produced mainly a kinetic controlled 5-OH product, but still achieved the 4'-OH modification and novoise-glycosylated products (with stronger base), as well as a diglycosylated compound. Read More

    Recent advances in the synthesis of rare sugars using DHAP-dependent aldolases.
    Carbohydr Res 2017 Nov 18;452:108-115. Epub 2017 Oct 18.
    Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, 214122, China. Electronic address:
    The occurrence rates of non-communicable diseases like obesity, diabetes and hyperlipidemia have increased remarkably due to excessive consumption of a high-energy diet. Rare sugars therefore have become increasingly attractive owing to their unique nutritional properties. In the past two decades, various rare sugars have been successfully prepared guided by the "Izumoring strategy". Read More

    Base-modified GDP-mannose derivatives and their substrate activity towards a yeast mannosyltransferase.
    Carbohydr Res 2017 Nov 21;452:91-96. Epub 2017 Sep 21.
    School of Pharmacy, University of East Anglia, Norwich, UK; King's College London, Department of Chemistry, Faculty of Natural & Mathematical Sciences, Britannia House, 7 Trinity Street, London, SE1 1DB, UK. Electronic address:
    We have previously developed a new class of inhibitors and chemical probes for glycosyltransferases through base-modification of the sugar-nucleotide donor. The key feature of these donor analogues is the presence of an additional substituent at the nucleobase. To date, the application of this general concept has been limited to UDP-sugars and UDP-sugar-dependent glycosyltransferases. Read More

    NKT-cell glycolipid agonist as adjuvant in synthetic vaccine.
    Carbohydr Res 2017 Nov 17;452:78-90. Epub 2017 Oct 17.
    Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, PR China. Electronic address:
    NKT cells are CD1d-restricted, glycolipid antigen-reactive, immunoregulatory T lymphocytes that can serve as a bridge between the innate and adaptive immunities. NKT cells have a wide range of therapeutic application in autoimmunity, transplant biology, infectious disease, cancer, and vaccinology. Rather than triggering "danger signal" and eliciting an innate immune response, αGalCer-based NKT-cell agonist act via a unique mechanism, recruiting NKT cells which play a T helper-like role even without peptide as Th epitope. Read More

    Novel 1,2-cis-stereoselective glycosylations utilizing organoboron reagents and their application to natural products and complex oligosaccharide synthesis.
    Carbohydr Res 2017 Nov 12;452:64-77. Epub 2017 Oct 12.
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
    In this mini-review article, 1,2-cis-stereoselective glycosylation methods utilizing organoboron reagents and 1,2-anhydroglycosyl donors that were developed in our laboratory, including regio- and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived boronic ester catalysts and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived borinic ester catalysts, are recounted. Representative applications of these methods to the synthesis of biologically active natural products and a complex oligosaccharide are also described. Read More

    Highly efficient synthesis of bioactive oleanane-type saponins.
    Carbohydr Res 2017 Nov 23;452:43-46. Epub 2017 Aug 23.
    The National Research Centre for Carbohydrate Synthesis, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang, 330022, China. Electronic address:
    Leveraging on Schmidt glycosylation method, a highly efficient approach to obtain oleanane-type triterpene saponins was fixed, whereby oleanyl mono-, disaccharide (guaianin N), trisaccharide (elatoside E), as well as tetrasaccharide (elatoside F) were obtained efficiently. The synthetic investigation has resulted in the discovery of the effect of branch-sugar incorporation sequence on the overall synthetic efficiency. Moreover, through bioactivity investigation, the cytotoxic activity of the obtained triterpenoid saponins was evaluated, and the preliminary structure-activity relationship was deduced. Read More

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