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Carbohydrate Research

Bin Liu, Jiaojiao Lu, Chunqing Ai, Bao Zhang, Li Guo, Shuang Song, Beiwei Zhu
Uronic acid-containing polysaccharides (UACPs) including well-known glycosaminoglycans (GAGs) and some non-GAGs exist widely in animal kingdom. Although numerous methods have been established to analyze GAGs, few methods are available for non-GAG UACPs. In the present study, a protocol to identify all kinds of UACPs with repeating disaccharide units of hexosamine and uronic acid was demonstrated, and UACP components in five shellfishes, namely Turritella fortilirata Sowerby (GTF), Batillaria zonalis (GBZ), Nassarius variciferus (GNV), Monodonta labio Linnaeus (GML), and Argopecten irradians Lamarck (BAI) were primarily revealed...
October 11, 2016: Carbohydrate Research
Julie Barbeau, Loïc Lemiègre, Allan Quelen, Virginie Malard, Haifei Gao, Cristine Gonçalves, Mathieu Berchel, Paul-Alain Jaffrès, Chantal Pichon, Patrick Midoux, Thierry Benvegnu
An archaeal diether lipid possessing a tri-antenna of α-D-mannopyranoside linked via an oligoethylene spacer to a (2S)-2-(phytanyloxy)-3-(hexadecyloxy)propanoic acid backbone (TriMan-Diether) was designed and synthesized. This new mannosylated lipid inserted in liposomes would show both DC-targeting and adjuvant properties thanks to the TriMan structure and the diether tail part, respectively.
October 11, 2016: Carbohydrate Research
Evgeny Vinogradov, Irina Sadovskaya, Thierry Grard, Marie-Pierre Chapot-Chartier
Lactobacillus casei is a Gram positive lactic acid bacterium used in dairy fermentations and present in the normal human gut microbiota. Certain strains are recognized as probiotics with beneficial effects on human and animal health. L. casei BL23 is a potential probiotic strain endowed with anti-inflammatory properties and a model strain widely used in genetic, physiological and biochemical studies. A number of bacterial cell surface polysaccharides have been shown to play a role in the immune modulation activities observed for probiotic lactic acid bacteria...
October 8, 2016: Carbohydrate Research
Harsha Amarasekara, David Crich
The synthesis and cyclization reactions, leading to spirocyclic medium ring-sized diolides, of o-(hydroxymethyl)xylylene monoesters of sialyl thioglycosides is described. Cyclization yields and stereoselectivities are found to vary as a function of the anomeric stereochemistry of the thioglycoside and of the N5 protecting group, and these effects are discussed in terms of the reaction mechanism. Cyclization in the presence of acetonitrile results in the isolation and characterization of a Ritter-type N-sialyl acetamide, which affords strong evidence for the participation of acetonitrile in the form of sialyl nitrilium ions...
October 8, 2016: Carbohydrate Research
Giuliana Righi, Emanuela Mandic', Carla Sappino, Ergys Dema, Paolo Bovicelli
Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-d-galactitol and its diastereoisomer 1,4-dideoxy-1,4-imino-d-glucitol is described, starting from a common optically active precursor. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereoselective nucleophilic openings of the corresponding chiral vinyl epoxide.
October 3, 2016: Carbohydrate Research
Ivan M Ryzhov, Elena Yu Korchagina, Alexander B Tuzikov, Inna S Popova, Tatiana V Tyrtysh, Galina V Pazynina, Stephen M Henry, Nicolai V Bovin
Seven lipophilic constructs containing Lewis (Le(a), Le(b), Le(y)) or chimeric Lewis/ABH (ALe(b), BLe(b), ALe(y), BLe(y)) glycans were obtained starting from corresponding oligosaccharides in form of 3-aminopropyl glycosides. ALe(b) and BLe(b) pentasaccharides were synthesized via [3 + 1] blockwise approach. The constructs (neoglycolipids, or FSLs) were inserted in erythrocyte membrane, and obtained "kodecytes" were used to map the immunochemical specificity of historical and contemporary monoclonal and polyclonal blood group system Lewis reagents...
September 28, 2016: Carbohydrate Research
Yang Yang, Hai-Peng Liu, Qun Yu, Mei-Bing Yang, De-Min Wang, Tian-Wei Jia, Hao-Jie He, Yun He, Hai-Xia Xiao, Suri S Iyer, Zhen-Chuan Fan, Xin Meng, Peng Yu
A new class of S-sialoside Human Serum Albumin (HSA) and Bovine Serum Albumin (BSA) conjugates were prepared to enhance the binding affinity to hemagglutinin (HA) and neuraminidase (NA). The valency of glycoconjugates was controlled by the reaction ratio of the S-sialoside monomer and protein. Hemagglutination inhibition assay showed that these synthetic glycoproteins have higher affinity to HA than the small clusters of sialosides with lower valency, due to multivalent effect and optimized three dimensional presentation of sialosides on the protein platform...
September 28, 2016: Carbohydrate Research
Diogo R B Ducatti, Madison A Carroll, David L Jakeman
A phosphorolytic activity has been reported for beta-N-acetylglucosaminidases from glycoside hydrolase family 3 (GH3) giving an interesting explanation for an unusual histidine as catalytic acid/base residue and suggesting that members from this family may be phosphorylases [J. Biol. Chem. 2015, 290, 4887]. Here, we describe the characterization of Hsero1941, a GH3 beta-N-acetylglucosaminidase from the endophytic nitrogen-fixing bacterium Herbaspirillum seropedicae SmR1. The enzyme has significantly higher activity against pNP-beta-D-GlcNAcp (Km = 0...
September 23, 2016: Carbohydrate Research
Sof'ya N Senchenkova, Xi Guo, Olesya I Naumenko, Alexander S Shashkov, Andrei V Perepelov, Bin Liu, Yuriy A Knirel
O-polysaccharides (OPSs) were obtained by mild acid degradation of the lipopolysaccharides of Escherichia coli O182-O187, and their structures were established by sugar analysis, Smith degradation, and (1)H and (13)C NMR spectroscopy. In addition to the monosaccharides that occur often in E. coli OPSs (d-Glc, d-Gal, d-Man, d-GlcNAc, d-GalNAc, d-GlcA, l-Fuc, d-Rib), a number of less common components were identified as the OPS constituents, including 2-acetamido-2-deoxy-l-quinovose and 4-deoxy-4-[(S)-3-hydroxybutanoyl-l-alanyl]-d-quinovose (O186), 3-acetamido-3-deoxy-d-fucose (O187), 3-deoxy-3-[(R)-3-hydroxybutanoyl]-d-fucose (O184), and 2,3-diacetamido-2,3-dideoxy-l-rhamnose (O182)...
September 23, 2016: Carbohydrate Research
Ethan D Goddard-Borger, Christina Tysoe, Stephen G Withers
Globoid cell leukodystrophy (GCL), or Krabbe disease, is a lysosomal storage disorder characterized by a deficiency in galactosylceramidase (GALC), which hydrolyses galactosylceramide and galactosylsphingosine (psychosine). Early detection of GCL in newborns is essential for timely therapeutic intervention and could be achieved by testing infant blood samples with isotopically labeled lysosmal enzyme substrates and mass spectrometry. While isotopically labeled psychosine would be a useful tool for the early diagnosis of GCL, its synthesis is lengthy and expensive...
September 22, 2016: Carbohydrate Research
Yannick Guinet, Laurent Carpentier, Laurent Paccou, Patrick Derollez, Alain Hédoux
Kinetics of isothermal crystallization of l-arabitol were analyzed from the undercooled liquid state within micron-sized droplets from micro-Raman spectroscopy. This study reveals that crystallization slightly above Tg is controlled by stochastic heterogeneous nucleation inherent to the droplet size. Microscopic Raman investigations performed in droplets give the unique opportunity to analyze the pure metastable Form II of l-arabitol. It was found that Form II is characterized by a molecular packing more compact than that of the stable Form I, inherent to strong intermolecular hydrogen bonding...
September 22, 2016: Carbohydrate Research
Ramu Petakamsetty, Anas Ansari, Ramesh Ramapanicker
A concise organocatalytic route toward the synthesis of furanose and pyranose substituted glycine and alanine derivatives is reported. These compounds are core structural units of some of the naturally available antibiotics and antifungal agents. Proline-catalyzed asymmetric α-amination of aldehydes derived from sugars is used as the key reaction to synthesize twelve sugar amino acid derivatives. The asymmetric transformations proceeded in good yields and with good to excellent diastereoselectivity. The application of the synthesized amino acids is demonstrated by synthesizing a tripeptide containing one of them...
September 21, 2016: Carbohydrate Research
Milica Fabišíková, Miroslava Martinková, Simona Hirková, Jozef Gonda, Martina Bago Pilátová, Gabriela Gönciová
The total synthesis of the anticancer agent (+)-spisulosine has been accomplished. The strategy involved a substrate-controlled aza-Claisen rearrangement to establish the erythro-configured amino-alcohol motif followed by deoxygenation to create a methyl side-chain. Subsequent Wittig olefination then permitted the construction of the carbon backbone of the target molecule. To investigate the antiproliferative effect of 1, its biological profile was examined on a panel of 6 human malignant cell lines and demonstrated the significant anticancer activity of 1 on at least five of the evaluated lines with IC50 < 1 μM (MCF-7, HTC-116, Caco-2, Jurkat and HeLa)...
September 21, 2016: Carbohydrate Research
Anna Kałuża, Anna Jarząb, Andrzej Gamian, Ewa M Kratz, Mariusz Zimmer, Mirosława Ferens-Sieczkowska
Glycosylation pattern within reproductive tract is now suggested to be involved in providing female immune tolerance for allograft sperm and developing embryo, but the information whether impaired glycosylation may influence male fertility potential is still limited. We have analyzed seminal plasma N-glycome in pooled samples derived from fertile and infertile men by means of MALDI-TOF/TOF tandem mass spectrometry. Among infertile subjects, normozoospermic, oligozoospermic, asthenozoospermic and oligoasthenozoospermic samples were obtained...
September 18, 2016: Carbohydrate Research
Megumi Maeda, Misato Tani, Takeo Yoshiie, Christopher J Vavricka, Yoshinobu Kimura
The Japanese cedar pollen allergen (Cry j1) and the mountain cedar pollen allergen (Jun a1) are glycosylated with plant complex type N-glycans bearing Lewis a epitope(s) (Galβ1-3[Fucα1-4]GlcNAc-). The biological significance of Lewis a type plant N-glycans and their effects on the human immune system remain to be elucidated. Since a substantial amount of such plant specific N-glycans are required to evaluate immunological activity, we have searched for good plant-glycan sources to characterize Lewis a epitope-containing plant N-glycans...
September 17, 2016: Carbohydrate Research
Tjerk J Sminia, Han Zuilhof, Tom Wennekes
This review discusses the advances in metabolic oligosaccharide engineering (MOE) from 2010 to 2016 with a focus on the structure, preparation, and reactivity of its chemical probes. A brief historical overview of MOE is followed by a comprehensive overview of the chemical probes currently available in the MOE molecular toolbox and the bioconjugation techniques they enable. The final part of the review focusses on the synthesis of a selection of probes and finishes with an outlook on recent and potential upcoming advances in the field of MOE...
September 16, 2016: Carbohydrate Research
Sandip R Khobare, Vikas Gajare, E Vishnuvardhan Reddy, Rajender Datrika, Malavika Banda, Vidavalur Siddaiah, Sharad S Pachore, Upadhya Timanna, Vilas H Dahanukar, U K Syam Kumar
A unique oxidative dehydration-oxidation of polyhydroxy-oxime (7) to the corresponding ketonitrile (8) in one pot is reported for the first time in carbohydrate literature. Key ketonitrile intermediate (8) upon palladium hydroxide mediated cascade reaction afforded 1-deoxynojirimycin (DNJ) 1b in moderate diastereoselectivity. The cascade reaction involves the conversion of nitrile to amine, heteroannulation, reduction of the imine and subsequent debenzylation to furnish the azasugars. This oxidative dehydration-oxidation and reductive heteroannulation methodology is successfully utilized for the total synthesis of 1-deoxynojirimycin (1b), miglitol (2) and miglustat (3)...
September 14, 2016: Carbohydrate Research
Kashmir Prasad Sethi, K P Ravindranathan Kartha
Preparation of a variety of per-O-acylated O- and S-glycosides of a set of commonly encountered mono- and disaccharides has been achieved effectively by solvent-free grinding of the corresponding acetylated/benzoylated glycosyl bromide and the desired acceptor alcohol/thiol in the presence of bismuth carbonate in a planetary ball mill. The method is simple, requires short reaction time periods and is practical allowing it to be performed at a milligram-to multi-gram scale as required. In the cases where the product is crystalline, it was often obtained in practically pure form by crystallization (and without the need for chromatographic isolation)...
September 13, 2016: Carbohydrate Research
Erik L Lindh, Malin Bergenstråhle-Wohlert, Camilla Terenzi, Lennart Salmén, István Furó
The interaction of water with cellulose stages many unresolved questions. Here (2)H MAS NMR and IR spectra recorded under carefully selected conditions in (1)H-(2)H exchanged, and re-exchanged, cellulose samples are presented. It is shown here, by a quantitative and robust approach, that only two of the three available hydroxyl groups on the surface of cellulose fibrils are exchanging their hydrogen with the surrounding water molecules. This finding is additionally verified and explained by MD simulations which demonstrate that the (1)HO(2) and (1)HO(6) hydroxyl groups of the constituting glucose units act as hydrogen-bond donors to water, while the (1)HO(3) groups behave exclusively as hydrogen-bond acceptors from water and donate hydrogen to their intra-chain neighbors O(5)...
September 10, 2016: Carbohydrate Research
Benedetta Bertolotti, Beáta Oroszová, Ieva Sutkeviciute, Ladislav Kniežo, Franck Fieschi, Kamil Parkan, Zuzana Lovyová, Martina Kašáková, Jitka Moravcová
The discovery of effective ligands for DC-SIGN receptor is one of the most challenging concepts of antiviral drug design due to the importance of this C-type lectin in infection processes. DC-SIGN recognizes mannosylated and fucosylated oligosaccharides but glycosidic linkages are accessible to both chemical and enzymatic degradations. To avoid this problem, the synthesis of stable glycoside mimetics has attracted increasing attention. In this work we establish for the first time mono- and divalent C-glycosides based on d-manno and l-fuco configurations as prospective DC-SIGN ligands...
September 9, 2016: Carbohydrate Research
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