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含有阿糖胺糖和N-(L-丙氨酰)-D-葡萄糖胺的产碱普罗威登斯菌O2 O-多糖的结构

Structure of the O-polysaccharide of Providencia alcalifaciens O2 containing ascarylose and N-(L-alanyl)-D-glucosamine.

作者信息

Ovchinnikova Olga G, Moryl Magdalena, Shashkov Alexander S, Chizhov Alexander O, Arbatsky Nikolay P, Shpirt Anna M, Rozalski Antoni, Knirel Yuriy A

机构信息

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation.

Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, PL 90-237 Lodz, Poland.

出版信息

Carbohydr Res. 2015 Jan 12;401:11-5. doi: 10.1016/j.carres.2014.10.016. Epub 2014 Oct 27.

DOI:10.1016/j.carres.2014.10.016
PMID:25464076
Abstract

The O-polysaccharide was obtained by degradation of the lipopolysaccharide of Providencia alcalifaciens O2 under mild acidic conditions followed by GPC. The polysaccharide was found to contain two unusual components: 3,6-dideoxy-L-arabino-hexose (ascarylose, Asc) and 2-(L-alanyl)amino-2-deoxy-D-glucose (GlcNAla). Ascarylose was partially split off during lipopolysaccharide degradation and could be eliminated completely by selective acid hydrolysis, which also partially cleaved the β-GAlNAc-(1 → 6) linkage. The following structure of the branched pentasaccharide repeating unit was established by (1)H and (13)C NMR spectroscopy of the O-polysaccharide and O-deacetylated polysaccharide, as well as products of partial acid hydrolysis: α-Ascp-(1 → 4)-α-D-GlcpA-(1 → 4) → 6)-β-D-GlcpNAla-(1 → 4)-β-D-GlpA-(1 → 3)-β-D-GalpNAc-(1 → ~60% OAc--3).

摘要

通过在温和酸性条件下对产碱普罗威登斯菌O2的脂多糖进行降解,随后进行凝胶渗透色谱(GPC),获得了O-多糖。发现该多糖含有两种不寻常的成分:3,6-二脱氧-L-阿拉伯己糖(阿糖胺,Asc)和2-(L-丙氨酰)氨基-2-脱氧-D-葡萄糖(GlcNAla)。阿糖胺在脂多糖降解过程中部分脱落,可通过选择性酸水解完全去除,该水解还部分切断了β-GAlNAc-(1→6)键。通过对O-多糖、O-脱乙酰化多糖以及部分酸水解产物进行(1)H和(13)C核磁共振光谱,确定了以下分支五糖重复单元的结构:α-Ascp-(1→4)-α-D-GlcpA-(1→4)→6)-β-D-GlcpNAla-(1→4)-β-D-GlpA-(1→3)-β-D-GalpNAc-(1→~60% OAc--3) 。

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