Search our Database of Scientific Publications and Authors

I’m looking for a

    10065 results match your criteria Carbohydrate research[Journal]

    1 OF 202

    Structural and genetic relatedness of the O-antigens of Escherichia coli O50 and O2.
    Carbohydr Res 2018 May 7;464:8-11. Epub 2018 May 7.
    N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation.
    An O-specific polysaccharide (O-antigen) was isolated by mild acid degradation of the lipopolysaccharide of Escherichia coli O50 followed by gel chromatography on Sephadex G-50. The following structure of the tetrasaccharide repeat was established by sugar analysis and 1D and 2D H and C NMR spectroscopy: →3)-α-l-Rhap-(1 → 2)-α-l-Rhap-(1 → 3)-β-l-Rhap-(1 → 4)-β-d-GlcpNAc-(1→ The linear O50 polysaccharide has the same structure as the main chain of the branched O polysaccharide of E. coli O2 studied earlier [Jansson et al. Read More

    Synthesis and glycosidase inhibition potency of all-trans substituted 1-C-perfluoroalkyl iminosugars.
    Carbohydr Res 2018 May 15;464:2-7. Epub 2018 May 15.
    Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims (ICMR), CNRS UMR 7312, UFR Sciences Exactes et Naturelles, BP 1039, F-51687 Reims Cedex 2, France. Electronic address:
    Synthetic analogues of the naturally occurring iminosugar homoDMDP, which feature a perfluoroalkyl group at the pseudo-anomeric position, have been synthesized from the corresponding sugar-derived cyclic aldonitrone. The new fluorinated iminosugars as well as homoDMDP and its 6-deoxy counterpart were evaluated for their inhibitory activity against a panel of glycosidases. While the replacement of the (1',2')-dihydroxyethyl substituent of homoDMDP with -CF proved detrimental for enzyme binding, introduction of a -CF moiety tuned the inhibitory activity spectrum selectively towards α-fucosidase and α-glucosidase from yeast. Read More

    Recent advances in the synthesis of cyclic 5'-nornucleoside phosphonate analogues.
    Carbohydr Res 2018 Apr 28;463:47-106. Epub 2018 Apr 28.
    College of Pharmacy, Chosun University, Kwangju 501-759, Republic of Korea. Electronic address:
    Nucleoside phosphonates are isosteric, isopolar, and isoelectronic with phosphates. Nucleoside phosphonates can undergo enzymatic phosphorylation for conversion into the corresponding diphosphoryl phosphonates, which are naturally occurring nucleoside triphosphate analogues. The biological activity, which is mostly antiviral and antitumor but sometimes is as specific enzyme inhibitor, is briefly presented to help discover compounds with increased activity over natural nucleosides to provide structure-activity data. Read More

    Quantification of anomeric structural changes of glucose solutions using near-infrared spectra.
    Carbohydr Res 2018 May 6;463:40-46. Epub 2018 May 6.
    Department of Pharmacology, Keio University School of Medicine, 160-8582, Japan; Keio Advanced Research Center for Water Biology and Medicine, Keio University, 108-8345, Japan; Keio Global Research Institute, 108-8345, Japan.
    Glucose is the most abundant carbohydrate found in living organisms. It exists as two anomers: α-D-glucose and β-D-glucose, which differ in how the hydroxyl group on the C1 carbon is directed. In solutions, the ratio between α- and β-D-glucose is typically 4:6 but can vary depending on the surrounding ions or temperature. Read More

    Structure of the LPS O-chain from Fusobacterium nucleatum strain MJR 7757 B.
    Carbohydr Res 2018 Apr 25;463:37-39. Epub 2018 Apr 25.
    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

    Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: Does the reaction proceed through 'axial rich' conformation?
    Carbohydr Res 2018 Apr 26;463:32-36. Epub 2018 Apr 26.
    Academy of Scientific and Innovative Research (AcSIR), India; Center for Materials Characterization, CSIR- National Chemical Laboratory, Pashan Road, Pune 411008, India. Electronic address:
    scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. This provides a potential route for the preparation of ring modified inositol derivatives. Read More

    Discovery and description of a new serogroup 7 Streptococcus pneumoniae serotype, 7D, and structural analysis of 7C and 7D.
    Carbohydr Res 2018 Apr 23;463:24-31. Epub 2018 Apr 23.
    Department of Chemistry, Technical University of Denmark, Kgs. Lyngby, Denmark. Electronic address:
    Streptococcus pneumoniae is characterised into 92 serotypes based on antigenic reactions of commercial rabbit sera to the capsular polysaccharides. During development of a bioinformatic serotyping tool (PneumoCaT), an isolate exhibited a novel codon at residue 385 of the glycosyltransferase gene wcwK encoding a distinct amino acid, which differentiates genogroup 7. Investigation by repeat serotyping and Quellung reaction revealed a novel pattern of factor sera with the isolate reacting very strongly with 7f, but also with 7e factor sera. Read More

    Synthesis of glyceryl glycosides related to A-type prymnesin toxins.
    Carbohydr Res 2018 Apr 17;463:14-23. Epub 2018 Apr 17.
    Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK. Electronic address:
    A suite of glycosylated glycerol derivatives representing various fragments of the glycosylated ichthyotoxins called prymnesins were chemically synthesised. Glycerol was used to represent a small fragment of the prymnesin backbone, and was glycosylated at the 2° position with the sugars currently reported to be present on prymnesin toxins. Neighbouring group participation was utilised to synthesise 1,2-trans-glycosides. Read More

    Cytotoxic and glycosaminoglycan priming activities of novel 4-anilinequinazoline β-D-xylosides.
    Carbohydr Res 2018 Apr 13;463:6-13. Epub 2018 Apr 13.
    Systems Biology & Medicine Center for Complex Diseases, Qingdao, 266071, PR China. Electronic address:
    β-D-xylosides with cytotoxic aglycones have augmented cytotoxicity towards animal cells because β-D-xyloside-primed glycosaminoglycans further enhance the aglycone's cytotoxicity. In this study, we designed and synthesized different 4-anilinequinazoline β-D-xylosides and found that compounds 7-10 possessing 3-chloro-4-((3-fluorobenzyl)oxy)aniline group as in anticancer drug lapatinib also primed glycosaminoglycans and were highly cytotoxic to cancer cells. Read More

    A rapid synthesis of sphingosine from phytosphingosine.
    Carbohydr Res 2018 Apr 13;463:1-5. Epub 2018 Apr 13.
    Department of Chemistry, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung City 402, Taiwan. Electronic address:
    A simple and efficient protocol for the synthesis of a sphingosine starting from cost-effective phytosphingosine has been described. Two alternative synthetic pathway have been disclosed based on the use of two different kinds of protective groups for the protection of the amino group in the phytosphingosine. The protected phytosphingosine was subsequently transformed into sphingosine in 5 steps i. Read More

    Synthesis of C-pyrimidyl nucleosides starting from alkynyl ribofuranosides.
    Carbohydr Res 2018 Jun 13;462:50-55. Epub 2018 Apr 13.
    Laboratoire de Chimie Biologique, EA 4505, University of Cergy-Pontoise, F-95000, Cergy-Pontoise, France. Electronic address:
    The synthesis of four C-pyrimidyl nucleosides is described by condensation of small nitrogen molecules (amidines and ureas) onto alkynyl riboside derivatives. These last compounds were obtained by indium mediated stereoselective alkynylation of suitably protected ribose derivatives and the condensation reaction conditions were studied in order to favor the N-attack of the nitrogen molecules leading to the pyrimidine ring formation. Read More

    Metal-free oxidative esterification of benzylated monosaccharides.
    Carbohydr Res 2018 Jun 12;462:45-49. Epub 2018 Apr 12.
    Laboratory LG2A, UMR CNRS 7378, UPJV, 33 rue saint leu, 80000, Amiens, France. Electronic address:
    Methyl glyconates have been attracting considerable attention as intermediates for the preparation of aryl C-glycosides, polyphenolic products, aliphatic polyesters, SGLT2 inhibitors, antibiotics etc … In view of the interest in those compounds, we report herein our work on the synthesis of methyl glyconates using an oxidative esterification carried out by molecular iodine. This reaction is catalyzed by non-toxic KFe(CN) that releases a small amount of cyanide ion into the reaction mixture. Four benzylated carbohydrates which contain a hemiacetalic functional group have been tested successfully. Read More

    Determination of the cell wall polysaccharide and teichoic acid structures from Lactococcus lactis IL1403.
    Carbohydr Res 2018 Jun 12;462:39-44. Epub 2018 Apr 12.
    Micalis Institute, INRA, AgroParisTech, Université Paris-Saclay, 78350, Jouy-en-Josas, France. Electronic address:
    In the lactic acid bacterium Lactococcus lactis, a cell wall polysaccharide (CWPS) is the bacterial receptor of the majority of infecting bacteriophages. The diversity of CWPS structures between strains explains, at least partially, the narrow host range of lactococcal phages. In the present work, we studied the polysaccharide components of the cell wall of the prototype L. Read More

    Structure and gene cluster of the O-antigen of Escherichia coli O54.
    Carbohydr Res 2018 Jun 5;462:34-38. Epub 2018 Apr 5.
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation.
    Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O54 afforded an O-polysaccharide, which was studied by sugar analysis, solvolysis with anhydrous trifluoroacetic acid, and H and C NMR spectroscopy. Solvolysis cleaved predominantly the linkage of β-d-Ribf and, to a lesser extent, that of β-d-GlcpNAc, whereas the other linkages, including the linkage of α-l-Rhap, were stable under selected conditions (40 °C, 5 h). The following structure of the O-polysaccharide was established: →4)-α-d-GalpA-(1 → 2)-α-l-Rhap-(1 → 2)-β-d-Ribf-(1 → 4)-β-d-Galp-(1 → 3)-β-d-GlcpNAc-(1→ The O-antigen gene cluster of E. Read More

    Molecular interactions of the anticancer agent ellipticine with glycosaminoglycans by in silico analysis.
    Carbohydr Res 2018 Jun 3;462:28-33. Epub 2018 Apr 3.
    Faculty of Chemistry, University of Gdańsk, ul. Wita Stwosza 63, 80-308 Gdańsk, Poland. Electronic address:
    The anticancer agent ellipticine (ELP) functions as a DNA intercalating drug. Depending on the pH of the medium, it exists both in a neutral and a protonated form. In acidic extracellular microenvironment characteristic to malignant tissues, charged ELP molecules can also bind to glycosaminoglycans (GAGs), linear anionic periodic polysaccharides, which interact with various protein targets affecting diverse cellular events. Read More

    Studies on the O-polysaccharide of Escherichia albertii O2 characterized by non-stoichiometric O-acetylation and non-stoichiometric side-chain l-fucosylation.
    Carbohydr Res 2018 May 6;461:80-84. Epub 2018 Mar 6.
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
    An O-polysaccharide was isolated from the lipopolysaccharide of Escherichia albertii O2 and studied by chemical methods and 1D and 2D H and C NMR spectroscopy. The following structure of the O-polysaccharide was established: . The O-polysaccharide is characterized by masked regularity owing to a non-stoichiometric O-acetylation of an l-fucose residue in the main chain and a non-stoichiometric side-chain l-fucosylation of a β-GlcNAc residue. Read More

    N-Glycosyltransferase from Aggregatibacter aphrophilus synthesizes glycopeptides with relaxed nucleotide-activated sugar donor selectivity.
    Carbohydr Res 2018 Jun 19;462:7-12. Epub 2018 Mar 19.
    The State Key Laboratory of Microbial Technology, National Glycoengineering Research Center and School of Life Sciences, Shandong University, Jinan, Shandong 250100, China. Electronic address:
    N-Glycosyltransferase (NGT) is an inverting glycosyltransferase for an unusual pathway of N-linked protein glycosylation and glycosylates polypeptides in the consensus sequon (N-(X≠P)-T/S) with hexose monosaccharides. Here, we expressed and characterized a novel N-glycosyltransferase from Aggregatibacter aphrophilus (named AaNGT). RP-HPLC and Mass Spectrometry were used to assay and quantify glycopeptide formation by AaNGT and determine its substrate specificities. Read More

    Comparative conformational studies of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyhex-1-enitols at the DFT level.
    Carbohydr Res 2018 Jun 28;462:13-27. Epub 2018 Mar 28.
    Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, PL-80-308, Gdańsk, Poland.
    B3LYP and M06-2X optimization and MP2 single point calculations are reported for the H and H conformations of 3,4,6-tri-O-acetyl-D-allal, 3,4,6-tri-O-acetyl-D-galactal, 3,4,6-tri-O-acetyl-D-glucal, and 3,4,6-tri-O-acetyl-D-gulal. Significant discrepancies in predictions of relative energies and conformers' population for B3LYP and M06-2X optimized geometries are observed. Generally, B3LYP overestimates the conformers' energies with respect to MP2, whereas M06-2X slightly underestimates the conformers' energies. Read More

    Structure of surface polysaccharides from Aeromonas sp. AMG272, a plant-growth promoting rhizobacterium isolated from rice rhizosphere.
    Carbohydr Res 2018 Jun 20;462:1-6. Epub 2018 Mar 20.
    Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Profesor García González, 1, 41012, Seville, Spain. Electronic address:
    Aeromonas sp. AMG272 is a Gram-negative bacterium that has been isolated from agricultural soil and studied for its plant growth-promoting activities. Structures of the O-specific polysaccharide chain of the AMG272 lipopolysaccharide and its capsular polysaccharide were elucidated using GLC-MS and NMR spectroscopy. Read More

    Structure of 3,6-dideoxy-3-[(R)-2-hydroxypropanoylamino]-D-galactose-containing O-polysaccharide from marine bacterium Simiduia litorea KMM 9504.
    Carbohydr Res 2018 May 21;461:76-79. Epub 2018 Mar 21.
    G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Prospekt 100 let Vladivostoku 159, Vladivostok, 690022, Russia; Far Eastern Federal University, Ul. Sukhanova 8, 690950, Vladivostok, Russia.
    The O-polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Simiduia litorea KMM 9504 and studied by chemical methods along with 1D and 2D H and C NMR spectroscopy including H,H-TOCSY, H,H-COSY, H,H-ROESY, H,C-HSQC and H,C-HMBC experiments. The following new structure of the O-polysaccharide of S. litorea KMM 9504 containing D-galacturonamide, 2-acetamido-2,6-dideoxy-D-glucose and 3,6-dideoxy-3-[(R)-2-hydroxypropanoylamino]-D-galactose was established. Read More

    Synthesis and self-assembling properties of 4,6-O-benzylidene acetal protected D-glucose and D-glucosamine β-1,2,3-triazole derivatives.
    Carbohydr Res 2018 May 23;461:60-75. Epub 2018 Feb 23.
    Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, VA, 23529, USA. Electronic address:
    Sugar based low molecular weight gelators (LMWGs) are useful small molecules that can form reversible supramolecular gels with many applications. Selective functionalization of common monosaccharides has resulted in several classes of effective LMWGs. Recently we found that certain peracetylated sugars containing anomeric triazole functional groups were effective gelators. Read More

    XRD and solid state C-NMR evaluation of the crystallinity enhancement of C-labeled bacterial cellulose biosynthesized by Komagataeibacter xylinus under different stimuli: A comparative strategy of analyses.
    Carbohydr Res 2018 May 16;461:51-59. Epub 2018 Mar 16.
    Departamento de Madera, Celulosa y Papel, CUCEI, Universidad de Guadalajara, Km 15.5, Carretera Guadalajara-Nogales, Las Agujas, C.P. 45020 Zapopan, Jalisco, Mexico. Electronic address:
    The production and crystallinity of C bacterial cellulose (BC) was examined in static culture of Komagataeibacter xylinus with different chemical and physical stimuli: the addition of NaCl or cloramphenicol as well as exposure to a magnetic field or to UV light. Crystalline BC biosynthesized under each stimulus was studied by XRD and solid state C NMR analyses. All treatments produced BC with enhanced crystallinity over 90% (XRD) and 80% (NMR) compared to the control (83 and 76%, respectively) or to Avicel (77 and 62%, respectively). Read More

    1-C-phosphonomethyl- and 1-C-difluorophosphonomethyl-1,4-imino-l-arabinitols as Galf transferase inhibitors: A comparison.
    Carbohydr Res 2018 May 17;461:45-50. Epub 2018 Mar 17.
    Institut de Chimie Organique et Analytique (ICOA), UMR 7311, Université d'Orléans et CNRS, Rue de Chartres, BP 6759, 45067 Orléans cedex 2, France. Electronic address:
    The convenient preparation of iminopentitol derivatives, based on a 1,4-dideoxy-1,4-imino-l-arabinitol scaffold carrying β-phosphono(difluoromethyl) or β-phosphonomethyl appendages, as Galf-1P mimics, is reported. The compounds were tested for their ability to inhibit GlfT2, a vital galactofuranosyltransferase involved in the cell wall biosynthesis of mycobacteria. Interestingly, the Galf-1P mimics lacking a fluorine atom (7 and 8) were very poor inhibitors, showing less than 20% inhibition of GlfT2, whereas compounds 2 and 3, which contains a difluoromethylenephosphonate moiety were more potent inhibitors. Read More

    Inositol to aromatics -benzene free synthesis of poly oxygenated aromatics.
    Carbohydr Res 2018 May 14;461:38-44. Epub 2018 Mar 14.
    Center for Materials Characterization, CSIR- National Chemical Laboratory, Pashan Road, Pune, 411008, India. Electronic address:
    A method for the preparation of benzene derivatives from myo-inositol, an abundantly available phyto chemical is described. 1,3-Bridged acetals of inososes undergo step-wise elimination leading to the formation of polyoxygenated benzene derivatives. This aromatization reaction proceeds through the intermediacy of a β-alkoxyenone, which could be isolated. Read More

    Synthesis of bidesmosidic lupane saponins - comparison of batch and continuous-flow methodologies.
    Carbohydr Res 2018 May 15;461:32-37. Epub 2018 Mar 15.
    Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
    Synthesis of lupane bidesmosides was optimized. The title compounds were obtained by glycosylation of 3-O- or 28-O-substituted betulin monodesmosides with Schmidt donors catalyzed by TMSOTf. Classical batch procedure and microreactor technique were used and compared in the above synthesis. Read More

    Structural studies of the cell wall polysaccharide from Lactococcus lactis UC509.9.
    Carbohydr Res 2018 May 17;461:25-31. Epub 2018 Mar 17.
    School of Microbiology, University College Cork, Western Road, Cork, Ireland; APC Microbiome Institute, University College Cork, Western Road, Cork, Ireland. Electronic address:
    Lactococcus lactis is the most widely utilised starter bacterial species in dairy fermentations. The L. lactis cell envelope contains polysaccharides, which, among other known functions, serve as bacteriophage receptors. Read More

    5-Acetamido-3,5-dideoxy-L-glycero-L-manno-non-2-ulosonic acid-containing O-polysaccharide from marine bacterium Pseudomonas glareae KMM 9500.
    Carbohydr Res 2018 May 8;461:19-24. Epub 2018 Mar 8.
    G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Prospect 100 let Vladivostoku, 159, Vladivostok, 690022, Russia; Far Eastern Federal University, Sukhanova St., 8, 690950, Vladivostok, Russia.
    The O-polysaccharide was isolated from the lipopolysaccharide of a marine bacterium Pseudomonas glareae KMM 9500 and studied by chemical methods along with 1D and 2D H and C NMR spectroscopy including H,H-TOCSY, H,H-COSY, H,H-ROESY, H,C-HSQC and H,C-HMBC experiments. The O-polysaccharide was found to consist of linear tetrasaccharide repeating units constituted by D-glucuronic acid (D-GlcA), L-rhamnose (L-Rha), D-glucose (D-Glc) and 5-acetamido-7,9-O-[(S)-1-carboxyethylidene]-3,5-dideoxy-L-glycero-L-manno-non-2-ulosonic acid (Sug7,9(S-Pyr)), partially O-acetylated at position 8 (∼70%): →4)-α-D-GlcpA-(1→3)-β-L-Rhap-(1→4)-β-D-Glcp-(1→4)-β-Sugp8Ac(∼70%)7,9(S-Pyr)-(2→. Read More

    Peruvioses A to F, sucrose esters from the exudate of Physalis peruviana fruit as α-amylase inhibitors.
    Carbohydr Res 2018 May 9;461:4-10. Epub 2018 Mar 9.
    Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Carrera 30 # 45-03, Bogotá D.C. 111321, Colombia. Electronic address:
    The fruit of Physalis peruviana is widely used in traditional Colombian medicine as an antidiabetic treatment. The aim of the study reported here was to identify the compounds responsible for the hypoglycemic activity using the α-amylase inhibition test. Bioguided fractionation of a dichloromethane extract of the sticky exudate that covers the fruit allowed the isolation and identification of three new sucrose esters, named as peruvioses C-E (1-3), along with the known peruvioses A (6), B (5) and F (4), the structures of which were elucidated by extensive NMR and MS experiments. Read More

    Charge effects of self-assembled chitosan-hyaluronic acid nanoparticles on inhibiting amyloid β-protein aggregation.
    Carbohydr Res 2018 May 8;461:11-18. Epub 2018 Mar 8.
    Department of Biochemical Engineering and Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin 300354, China.
    Amyloid β-protein (Aβ) aggregation is crucial for the pathogenesis of Alzheimer's disease, and surface charge of nanoparticles (NPs) has been recognized as an important factor influencing Aβ aggregation. Herein, we report a systematic study on the issue with a series of self-assembled chitosan-hyaluronic acid composite (CH) NPs of different surface charges (CH1 to CH7, zeta potentials from +38 to -35 mV). Both the positive and negative CH NPs inhibited Aβ aggregation and the inhibitory effect increased with increasing the surface charges density. Read More

    Pd(II)/PhI(OAc) promoted direct cross coupling of glucals with aromatic acids.
    Carbohydr Res 2018 May 12;461:1-3. Epub 2018 Mar 12.
    Centre for Semiochemicals, India. Electronic address:
    A highly efficient oxidative C2-aroyloxylation of D-glucal with aromatic carboxylic acids has been achieved for the first time using 5 mol% Pd(OAc) and 1 equiv of PhI(OAc) to produce C2-aroyloxyglycals in good yields. The use of excess of PhI(OAc) (2 equiv) provides C2-acyloxyglycal exclusively. Read More

    Efficient synthesis of a 6-deoxy-talose containing tetrasccharide found in Franconibacter helveticus LMG23732.
    Carbohydr Res 2018 May 26;460:57-65. Epub 2018 Feb 26.
    Department of Applied Chemistry, China Agricultural University, Beijing 100193, PR China. Electronic address:
    Synthesis of the 6-deoxy-talose (6-dTal) containing tetrasaccharide, naturally found in Franconibacter helveticus LMG23732T, has been described. The synthetic method utilized an allyloxyethylidene group for protecting the 1-OH and 2-OH groups of rhamnopyranose and a redox reaction for synthesizing 6-deoxy talose, which eventually formed a disaccharide containing α-Glcp-(1→2)-6dTalp configured glycosidic bonds using a [2 + 2] synthetic strategy. Read More

    Full structure and insight into the gene cluster of the O-specific polysaccharide of Yersinia intermedia H9-36/83 (O:17).
    Carbohydr Res 2018 May 28;460:51-56. Epub 2018 Feb 28.
    State Research Center for Applied Microbiology and Biotechnology, 142279, Obolensk, Moscow Region, Russia. Electronic address:
    Lipopolysaccharide was isolated from bacteria Yersinia intermedia H9-36/83 (O:17) and degraded with mild acid to give an O-specific polysaccharide, which was isolated by GPC on Sephadex G-50 and studied by sugar analysis and 1D and 2D NMR spectroscopy. The polysaccharide was found to contain 3-deoxy-3-[(R)-3-hydroxybutanoylamino]-d-fucose (d-Fuc3NR3Hb) and the following structure of the heptasaccharide repeating unit was established: The structure established is consistent with the gene content of the O-antigen gene cluster. The O-polysaccharide structure and gene cluster of Y. Read More

    Structure and genetics of a glycerol 2-phosphate-containing O-specific polysaccharide of Escherichia coli O33.
    Carbohydr Res 2018 May 17;460:47-50. Epub 2018 Feb 17.
    N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation.
    An O-specific polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Escherichia coli O33 followed by gel-permeation chromatography on Sephadex G-50. The polysaccharide was found to contain glycerol 2-phosphate (Gro-2-P), and the following structure of its tetrasaccharide repeat was established by sugar analysis, dephosphorylation, and 1D and 2D H and C NMR spectroscopy: The O33-antigen gene cluster was analyzed and found to be essentially consistent with the O-polysaccharide structure. Read More

    Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D.
    Carbohydr Res 2018 May 2;460:41-46. Epub 2018 Mar 2.
    School of Pharmacy, Fudan University, Shanghai 201203, China. Electronic address:
    Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)-NaBH system in one pot. Read More

    Configuration-dependent complex formation between Ca(II) and sugar carboxylate ligands in alkaline medium: Comparison of L-gulonate with D-gluconate and D-heptaguconate.
    Carbohydr Res 2018 May 23;460:34-40. Epub 2018 Feb 23.
    Department of Inorganic and Analytical Chemistry, University of Szeged, 7 Dóm tér, H-6720 Szeged, Hungary. Electronic address:
    The calcium sugar carboxylate interactions in hyperalkaline solutions are of relevance in radioactive waste repositories and in certain industrial processes. The complex formation between L-gulonate and Ca ions was studied in strongly alkaline medium at 25 °C and 1 M ionic strength and was compared with previous results reported for D-gluconate and D-heptagluconate. The deprotonation of the ligand was confirmed by potentiometric and C NMR spectroscopic measurements. Read More

    Synthesis of novel sugar or azasugar modified anthra[1,2-d] imidazole-6,11-dione derivatives and biological evaluation.
    Carbohydr Res 2018 May 20;460:29-33. Epub 2018 Feb 20.
    Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China; Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding, 071002, China. Electronic address:
    A series of novel, sugar or azasugar modified anthra[1,2-d] imidazole-6,11-dione derivatives, with different side chain were synthesized, using the synthetic route of imidazole cyclization reaction of 1,2-diaminoanthraquinone with various sugar (azasugar)-derived aldehydes, and imidazole cyclization reaction of 1,2-diaminoanthraquinone with chloroacetic acid and then followed by the nucleophilic substitution of N-alkylamino azasugar. Their biological activities against HIV-RT and cytotoxic activities against A549, Hela and MCF-7 cells were preliminary evaluated, most compounds showed similar HIV-RT inhibition to the control drug (AZT). Read More

    Efficient glycosylation of natural Danshensu and its enantiomer by sugar and 2-deoxy sugar donors.
    Carbohydr Res 2018 May 23;460:19-28. Epub 2018 Feb 23.
    Pharmaceutical Research Institute, 8 Rydygiera Street, 01-793 Warsaw, Poland.
    An efficient methodology of the glycosylation process of a secondary plant metabolite (R-Danshensu) and its enantiomer by sugar and 2-deoxy sugar donors was developed. The overall synthesis of the new sugar derivatives involved two steps, starting from the previously synthesized protected R and S Danshensu (1 and 2). The deoxy sugar derivatives of R and S Danshensu were obtained from available tri-O-acetyl-2-deoxy-D-glucal and di-O-acetyl-2-deoxy-D-ramnal. Read More

    Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals.
    Carbohydr Res 2018 Feb 19. Epub 2018 Feb 19.
    Department of Organic Chemistry, University of Debrecen, POB 400, H-4002 Debrecen, Hungary. Electronic address:
    Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiOtBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds. Read More

    Mechanochemical depolymerization of inulin.
    Carbohydr Res 2018 May 19;460:14-18. Epub 2018 Feb 19.
    Department of Food Science and Agricultural Chemistry, Macdonald Campus, McGill University, Montreal, Canada. Electronic address:
    Although chemical reactions driven by mechanical force is emerging as a promising tool in the field of physical sciences, its applications in the area of food sciences are not reported. In this paper, we propose ball milling as an efficient tool for the controlled generation of fructooligosaccharide (FOS) mixtures from inulin with a degree of polymerization (dp) ranging between 4 and 7. The addition of catalytic amounts of AlCl together with ball milling (30 min, at 30 Hz) generated mixtures rich in dehydrated disaccharides such as di-D-fructose dianhydrides. Read More

    Preparation and structural characterization of regioselective 4-O/6-O-desulfated chondroitin sulfate.
    Carbohydr Res 2018 May 2;460:8-13. Epub 2018 Feb 2.
    Key Laboratory of Marine Drugs, Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycoengineering, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China; Marine Biomedical Research Institute of Qingdao, Qingdao 266071, China. Electronic address:
    The sulfation pattern plays a crucial role in chondroitin sulfate (CS) biological activity, and preparation of CS with defined structure is essential for accurate pharmacological study. In this study, we focused on the preparation of regioselective 4-O/6-O-desulfated CS derived from porcine, employing a dimethyl sulfoxide-methanol (DMSO-MeOH) method and an N-methyl-N-(trimethylsilyl) -trifluoroacetamide (MTSTFA) method CS, respectively. Results showed that the sulfate at C4 position (4-O-S) of N-acetylgalactosamine (GalNAc) was selectively removed by the DMSO-MeOH method, and the sulfate at C6 position (6-O-S) of GalNAc was selectively removed by the MTSTFA method. Read More

    β-L-Arabinofuranosylation Conducted by 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl Trichloroacetimidate.
    Carbohydr Res 2018 May 13;460:1-7. Epub 2018 Feb 13.
    School of Chemistry Engineering, Sichuan University of Science & Engineering, Zigong 643000, China. Electronic address:
    We describe a β-L-arabinofuranosylation method by employing the 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl trichloroacetimidate 10 as a donor. This approach allows a wide range of acceptor substrates, especially amino acid acceptors, to be used. Stereoselective synthesis of β-(1,4)-L-arabinofuranosyl-(2S, 4R)-4-hydroxy-L-proline (β-L-Araf-L-Hyp) and its dimer is achieved readily by this method. Read More

    Scope and limitations of carbohydrate hydrolysis for de novo glycan sequencing using a hydrogen peroxide/metallopeptide-based glycosidase mimetic.
    Carbohydr Res 2018 Mar 3;458-459:85-88. Epub 2018 Feb 3.
    Department of Chemistry, Indiana University, Bloomington, IN, USA; Radcliffe Institute of Advanced Study, Harvard University, Cambridge, MA, USA. Electronic address:
    Acidic hydrolysis is commonly used as a first step to break down oligo- and polysaccharides into monosaccharide units for structural analysis. While easy to set up and amenable to mass spectrometry detection, acid hydrolysis is not without its drawbacks. For example, ring-destruction side reactions and degradation products, along with difficulties in optimizing conditions from analyte to analyte, greatly limits its broad utility. Read More

    Site-specific immobilization of endoglycosidases for streamlined chemoenzymatic glycan remodeling of antibodies.
    Carbohydr Res 2018 Mar 15;458-459:77-84. Epub 2018 Feb 15.
    Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA. Electronic address:
    Chemoenzymatic glycan remodeling of antibodies using an endoglycosidase and its mutant is emerging as an attractive approach for producing homogeneous antibody glycoforms. We report in this paper a site-specific covalent immobilization of the endoglycosidases (Endo-S2 and its glycosynthase mutant D184M) using a recombinant microbial transglutaminase (MTG) and evaluation of the immobilized enzymes in deglycosylation and glycosylation of a therapeutic antibody. The site-specific covalent immobilization was achieved by introduction of a Q-tag at the C-terminus of the recombinant enzymes followed by conjugation of the enzymes to a primary amine-containing solid support through MTG-catalyzed transglutamination. Read More

    Preparation and functional analysis of gossypols having two carbohydrate appendages with enaminooxy linkages.
    Carbohydr Res 2018 Mar 14;458-459:67-76. Epub 2018 Feb 14.
    Faculty of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun, Gumma 374-0193, Japan; Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe, Saitama 350-8585, Japan. Electronic address:
    We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6. Read More

    A new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides.
    Carbohydr Res 2018 Mar 12;458-459:60-66. Epub 2018 Feb 12.
    Tomsk State University, Lenin Avenue 36, Tomsk 634050, Russia.
    In the present work we report that acetyl groups of per - acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. Read More

    NMR analysis of substrate binding to a two-domain chitinase: Comparison between soluble and insoluble chitins.
    Carbohydr Res 2018 Mar 8;458-459:52-59. Epub 2018 Feb 8.
    Department of Advanced Bioscience, Kindai University, 3327-204 Nakamachi, Nara 631-8505, Japan. Electronic address:
    CJP-4 is a two-domain chitinase from Japanese cedar (Cryptomeria japonica) pollen, consisting of an N-terminal CBM18 domain and a GH19 catalytic domain. The substrate binding to an inactive mutant protein of full-length CJP-4, in which the catalytic acid Glu108 was mutated to glutamine, CJP-4(E108Q), was analyzed by NMR spectroscopy. Based on the chemical shift perturbations of H-N HSQC signals of Gly26 (CBM18 domain) and Trp185 (GH19 domain), the association constants for individual domains of CJP-4(E108Q) toward soluble chitin hexamer (GlcNAc) were determined to be 2300 and 3500 M, respectively. Read More

    Simultaneous formation of 3-deoxy-d-threo-hexo-2-ulose and 3-deoxy-d-erythro-hexo-2-ulose during the degradation of d-glucose derived Amadori rearrangement products: Mechanistic considerations.
    Carbohydr Res 2018 Mar 12;458-459:44-51. Epub 2018 Feb 12.
    Berlin Institute of Technology, Department of Food Chemistry and Food Analysis, Gustav-Meyer-Allee 25, TIB 4/3-1, D-13355 Berlin, Germany. Electronic address:
    Analyzing classical model reaction systems of Amadori rearrangement products (ARP) it became apparent that the formation of 3-deoxy-d-threo-hexo-2-ulose (3-deoxygalactosone, 3-DGal) during the degradation of ARPs is highly dependent on pH and the amino acid residue of the respective ARP. Based on a detailed analysis of the NMR chemical shifts of the sugar moieties of different ARPs, it could be derived that the formation of 3-DGal is sensitive to the stability of a co-operative hydrogen bond network which involves HO-C3, the deprotonated carboxyl functionality and the protonated amino nitrogen of the amino acid substituent. Participating in this bond network, HO-C3 is partially protonated which facilitates the elimination of water at C3. Read More

    Stereocontrolled synthesis of oleanolic saponin ladyginoside A isolated from Ladyginia bucharica.
    Carbohydr Res 2018 Mar 8;458-459:35-43. Epub 2018 Feb 8.
    Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Krakow, Poland; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. Electronic address:
    Efficient stereocontrolled synthesis of ladyginoside A isolated from Ladyginia bucharica is described. The presented methodology bases on the β-selective glycosylation to construct oleanate-3-O-β-glycoside from selectively protected d-cellobiose comprising desired β-linkage in carbohydrate unit. By using this procedure, dimethyl ester of ladyginoside A (1) (methyl oleanate 3-O-(β-d-glucopyranosyl)-(1 → 4)-β-d-glucuronide methyl ester) was obtained in 16% overall yield. Read More

    Partially methylated galactans containing different proportions of 3-O-methyl-galactose from Pleurotus citrinopileatus.
    Carbohydr Res 2018 Mar 6;458-459:29-34. Epub 2018 Feb 6.
    Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, 81531-980 Curitiba, Brazil.
    Pleurotus citrinopileatus, popularly known as "golden oyster mushroom" have medicinal properties, which are attributed mainly to the presence of bioactive polysaccharides. In this work, two partially 3-O-methylated galactans were isolated from the fruiting bodies of this fungus, via successive aqueous extraction, followed by fractionation by freeze-thawing, and precipitation of soluble material with Fehling solution. The structural assignments were carried out using mono- and bidimensional NMR spectroscopy, monosaccharide composition, and methylation analyses. Read More

    1 OF 202