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Carbohydrate Research

Guillaume Goyette-Desjardins, Evgeny Vinogradov, Masatoshi Okura, Daisuke Takamatsu, Marcelo Gottschalk, Mariela Segura
Streptococcus suis serotype 3 is counted among the S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 3 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence for serotype 3: [4)D-GlcA (β1-3)d-QuiNAc4NAc(β1-]n . To the best of our knowledge, this is the first report of di-N-acetyl-d-bacillosamine (QuiNAc4NAc) containing polysaccharides in Streptococci and the second time this rare diamino sugar has been observed in a Gram-positive bacterial species since its initial report...
July 7, 2018: Carbohydrate Research
Zhenjun Zhu, Beiwei Zhu, Chunqing Ai, Jiaojiao Lu, Sufeng Wu, Yili Liu, Linlin Wang, Jingfeng Yang, Shuang Song, Xiaoling Liu
Fucosylated chondroitin sulfate (FCS) and fucoidan (FUC) are two main bioactive polysaccharides in sea cucumbers. A novel method for quantitation of FCS and FUC was developed by detecting chondroitin disaccharide and fucose produced through acid hydrolysis using HPLC-MS/MS. The present method showed satisfactory performance for both saccharides. It was applied to assay sea cucumbers (Stichopus japonicus) reared in pond grow-out or bottom sowing, and the results were compared with those obtained by traditional HPLC method and 1,9-dimethylmethylene blue test, which could only provide the total sea cucumber polysaccharide (SCP) contents...
July 3, 2018: Carbohydrate Research
Xue Liu, Sujian Cao, Ling Qin, Meijia He, Hui Sun, Yajing Yang, Xiao Liu, Wenjun Mao
A sulfated polysaccharide, designated MAP2, was isolated from Monostroma angicava by water extraction, anion-exchange and size-exclusion chromatography. The structural characteristics of MAP2 were investigated by chemical and spectroscopic methods, including methylation analysis, one- and two-dimensional nuclear magnetic resonance and electrospray mass spectrometry with collision-induced dissociation spectroscopic analyses. The results showed that MAP2 was primarily composed of rhamnose with small amounts of xylose, glucuronic acid and glucose...
June 26, 2018: Carbohydrate Research
Jason Hlozek, Michelle M Kuttel, Neil Ravenscroft
Neisseria meningitidis is a major cause of bacterial meningitis worldwide especially in Africa. The capsular polysaccharide (CPS) is the main virulence factor and the target antigen for polysaccharide and conjugate vaccines. The high burden of serogroup A disease in the Meningitis Belt of sub-Saharan Africa led to the introduction of MenAfriVac® , which has successfully reduced the number of cases of group A disease. However, several outbreaks caused by other serogroups have been reported, including those due to serogroup X...
June 22, 2018: Carbohydrate Research
Huifang Yin, Lubbert Dijkhuizen, Sander S van Leeuwen
Oligosaccharides derived from lactulose (β-D-Galp-(1 → 4)-D-Fru) are drawing more and more attention nowadays because of their strong resistance to gut digestion, and the interest to discover novel prebiotics. Compared to galactooligosaccharides, currently known structures of lactulose oligosaccharides are very limited. In this study, the wild-type β-galactosidase BgaD-D of Bacillus circulans ATCC 31382, as well as the derived mutant R484H, were used to synthesize oligosaccharides from lactulose. In total, 9 oligosaccharide structures were identified by MALDI-TOF-MS and NMR spectroscopy analysis...
June 19, 2018: Carbohydrate Research
Aline Teixeira Maciel E Silva, Ana Luiza Chaves Maia, Juliana de Oliveira Silva, André Luis Branco de Barros, Daniel Crístian Ferreira Soares, Mariana Torquato Quezado de Magalhães, Ricardo José Alves, Gilson Andrade Ramaldes
Carbohydrate receptors on liver represent attractive targets for receptor-mediated delivery of nanostructured therapeutics. In this study, two new cholesterol-based glycoconjugates derived from d-galactose and N-acetylglucosamine were synthesized and incorporated into liposomes. 99m Tc-Cholesterol-DTPA complex was used for radiolabeling experiments in vivo with high radiochemical yields and stability. Biodistribution studies confirmed the targeting of galactosylated liposomes (GalL) to liver cells. These results indicated that GalL could be considered a promising drug delivery system for liver diseases therapy...
June 18, 2018: Carbohydrate Research
Evelina L Zdorovenko, Alexander S Shashkov, Alexandra A Kadykova, Elena P Kiseleva, Victoria V Savich, Galina I Novik, Yuriy A Knirel
Strain of Pseudomonas psychrotolerans was cultured on the nutrient agar and in a liquid nutrient broth. Bacterial cells were phage-typed with bacteriophages specific to Pseudomonas. O-antigen was isolated from cells using phenol-water method and mild acid degradation. The following structures of the polysaccharides extracted were established by sugar analysis and 1D, 2D NMR spectroscopy: PSI→3)-α-D-Manp-(1→2)-α-D-Manp-(1→; PSII→3)-α-D-Rhap-(1→2)-β-D-Rhap-(1→3)-α-D-Rhap-(1→; α-D-Glcp-(1˩; 2...
June 18, 2018: Carbohydrate Research
Takashi Matsumoto, Takuya Nakajima, Takehiro Iwadate, Ken-Ichi Nihei
Isotachioside (1) and its related natural product 2 are isolated from Isotachis japonica and Protea neriifolia, respectively, and are categorized as analogs of arbutin (3), a tyrosinase inhibitor for practical use. Both of the natural products and several derivatives such as glucoside 4, xyloside 5, cellobioside 6, and maltoside 7 were synthesized via Schmidt glycosylation as a key step, and their tyrosinase inhibitory activity was evaluated. The half maximal inhibitory concentration (IC50 ) of 1-3 could not be determined even when the concentration was increased to 1000 μM...
June 8, 2018: Carbohydrate Research
Quntao Liang, Pradeep Chopra, Geert-Jan Boons, Joshua S Sharp
The structure of heparin and heparan sulfate (Hep/HS) oligosaccharides, as determined by the length and the pattern of sulfation, acetylation, and uronic acid epimerization, dictates their biological function through modulating interactions with protein targets. But fine structural determination is a very challenging task due to the lability of the sulfate modifications and difficulties in separating isomeric HS chains. Previously, we reported a strategy for chemical derivatization involving permethylation, desulfation, and trideuteroperacetylation, combined with standard reverse phase LC-MS/MS that enables the structural sequencing for heparin/HS oligosaccharides of sizes up to dodecasaccharide by positionally replacing all sulfates with more stable trideuteroacetyl groups, allowing for robust MS/MS sequencing...
June 8, 2018: Carbohydrate Research
Elena N Sigida, Yuliya P Fedonenko, Alexander S Shashkov, Svetlana A Konnova, Vladimir V Ignatov
O-specific polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide of nitrogen-fixing bacterium Azospirillum fermentarium CC-LY743T (IBPPM 578) and was studied by sugar analysis along with 1 H and 13 C NMR spectroscopy, including 1 H,1 H COSY, TOCSY, ROESY, and 1 H,13 C HSQC and HMBC experiments. The polysaccharide was found to be linear and to consist of alterating α-l-fucose and α-d-mannose residues in tetrasaccharide repeating units of the following structure: →2)-α-D-Manp-(1 → 3)-α-L-Fucp-(1 → 3)-α-D-Manp-(1 → 3)-α-L-Fucp-(1→...
June 6, 2018: Carbohydrate Research
Sateesh Dubbu, Ashish Kumar Verma, Kadigachalam Parasuraman, Yashwant D Vankar
Synthesis of 1,2-annulated-C-aryl glycosides has been achieved in a stereoselective manner through the Diels-Alder reaction between carbohydrate-derived terminally unsubstituted dienes and in situ generated arynes. In these reactions, formation of sugar-fused (or branched) naphthalenes was also observed and found to be temperature dependent and thus constituting one of the salient features of this work. The synthetic importance of 1,2-annulated-C-aryl glycosides has been explored by transforming them into densely oxygenated products by functionalizing the unsubstituted exo-double bond...
June 6, 2018: Carbohydrate Research
Yue Chu, Jin-Song Yang
The efficient synthesis of a linear pentasaccharide with the structure 1, β-D-Araf-(1 → 2)-α-D-Araf-(1 → 5)-α-D-Araf-(1 → 5)-α-D-Araf-(1 → 5)-α-D-Araf-(1 → 5), as its octyl glycoside has been achieved through a convergent [3 + 2] coupling strategy. The difficult-to-obtain 1,2-cis-β-arabinofuranosidic bond at the non-reducing end of the target molecule was stereoselectively constructed by the use of a 2-quinolinecarbonyl-directed 1,2-cis glycosylation method.
May 29, 2018: Carbohydrate Research
Nicole C McKenzie, Nichollas E Scott, Alan John, Jonathan M White, Ethan D Goddard-Borger
Many monoclonal antibodies (mAbs) used in cancer immunotherapy mediate tumour cell lysis by recruiting natural killer (NK) cells; a phenomenon known as antibody-dependent cellular cytotoxicity (ADCC). Eliminating core-fucose from the N-glycans of a mAb enhances its capacity to induce ADCC. As such, inhibitors of fucosylation are highly desirable for the production of mAbs for research and therapeutic use. Herein, we describe a simple synthesis of 6,6,6-trifluoro-l-fucose (F3Fuc), a metabolic inhibitor of fucosylation, and demonstrate the utility of this molecule in the production of low-fucose mAbs from murine hybridoma cell lines...
May 23, 2018: Carbohydrate Research
Olesya I Naumenko, Jingjie Song, Sof'ya N Senchenkova, Xiaohan Jiang, Andrei V Perepelov, Alexander S Shashkov, Yuriy A Knirel
Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O57 afforded an O-polysaccharide, which was isolated by gel permeation chromatography (GPC) and studied by sugar analysis, Smith degradation and solvolysis with trifluoroacetic acid, along with 2D 1 H and 13 C NMR spectroscopy. The O-polysaccharide was found to contain d-Glc, d-Gal, d-GalA, d-GlcNAc, and l-FucNAc, as well as O-acetyl groups. Smith degradation of the O-deacetylated polysaccharide destroyed side-branch β-Glсp and α-GalpA to give a modified linear polysaccharide...
May 19, 2018: Carbohydrate Research
Masae Hosoda, Yushi Takahashi, Masaaki Shiota, Daisuke Shinmachi, Renji Inomoto, Shinichi Higashimoto, Kiyoko F Aoki-Kinoshita
Glycan-binding protein (GBP) interaction experiments, such as glycan microarrays, are often used to understand glycan recognition patterns. However, oftentimes the interpretation of glycan array experimental data makes it difficult to identify discrete GBP binding patterns due to their ambiguity. It is known that lectins, for example, are non-specific in their binding affinities; the same lectin can bind to different monosaccharides or even different glycan structures. In bioinformatics, several tools to mine the data generated from these sorts of experiments have been developed...
July 15, 2018: Carbohydrate Research
Polina I Abronina, Alexander I Zinin, Denis A Romashin, Valeria V Tereshina, Alexander O Chizhov, Leonid O Kononov
Both protective and pre-spacer features of 4-(2-chloroethoxy)phenyl (CEP) aglycon, which belong to the class of Janus aglycons, were engaged in a benzyl-free synthesis of oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7. Introduction of α-1,4-linked L-fucose residue was performed using 3,4-di-O-benzoyl-2-O-triisopropylsilyl-α-L-fucopyranosyl N-phenyltrifluoroacetimidate in excellent stereoselectivity and high yields. The obtained deprotected di-, tri- and tetrasaccharides contain 4-(2-azidoethoxy)phenyl (AEP) spacer aglycon, which allows straightforward preparation of neoglycoconjugates that will be used for the study of the role of lipopolysaccharide of rhizobacterium A...
July 15, 2018: Carbohydrate Research
Yuyang Zhu, Maomao Yan, Yi Lasanajak, David F Smith, Xuezheng Song
Despite the important advances in chemical and chemoenzymatic synthesis of glycans, access to large quantities of complex natural glycans remains a major impediment to progress in Glycoscience. Here we report a large-scale preparation of N-glycans from a kilogram of commercial soy proteins using oxidative release of natural glycans (ORNG). The high mannose and paucimannose N-glycans were labeled with a fluorescent tag and purified by size exclusion and multidimensional preparative HPLC. Side products are identified and potential mechanisms for the oxidative release of natural N-glycans from glycoproteins are proposed...
July 15, 2018: Carbohydrate Research
Ying Cai, Wenjiao Yang, Ronghua Yin, Lutan Zhou, Zhongkun Li, Mingyi Wu, Jinhua Zhao
A fucan sulfate was isolated and purified from the sea cucumber Holothuria albiventer by papain enzymolysis, alkaline hydrolysis and ion-exchange chromatography. The water-soluble polysaccharide had high molecular weight and contained fucose and sulfate in a molar ratio of about 1:0.83. Methylation analysis of the native polysaccharide indicated that its glycosidic linkages and sulfate substituents might be at O-3 or O-3, 4 or O-2, 3, or O-2, 3, 4 positions. FT-IR and 2D NMR spectroscopies further revealed that the fucan sulfate is characteristically composed of a regular α (1 → 3) linked hexasaccharide repeating unit which is substituted with sulfate esters in a distinctive pattern...
July 15, 2018: Carbohydrate Research
Bin Yang, Sof'ya N Senchenkova, Olesya I Naumenko, Alexander S Shashkov, Bin Liu, Andrey V Perepelov, Yuriy A Knirel
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 1 H and 13 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...
July 15, 2018: Carbohydrate Research
Fabien Massicot, Richard Plantier-Royon, Jean-Luc Vasse, Jean-Bernard Behr
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 -C4 F9 proved detrimental for enzyme binding, introduction of a -C3 F7 moiety tuned the inhibitory activity spectrum selectively towards α-fucosidase and α-glucosidase from yeast...
July 15, 2018: Carbohydrate Research
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