The acidic specific capsular polysaccharide of Rhodococcusequi serotype 3. Structural elucidation and stereochemical analysis of the lactate ether and pyruvate acetal substituents
The acidic specific capsular polysaccharide of Rhodococcusequi serotype 3. Structural elucidation and stereochemical analysis of the lactate ether and pyruvate acetal substituents
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红球菌血清型 3 的酸性特异性荚膜多糖。乳酸酯醚和丙酮酸酯缩醛取代基的结构阐明和立体化学分析
DOI：
10.1139/v92-336
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发表时间：
1992
影响因子：
1.1
通讯作者：
J. Richards
中科院分区：
文献类型：
--
作者：
W. Severn;J. Richards
马红球菌血清型3产生的特异性荚膜多糖被发现是由D-葡萄糖、D-半乳糖、D-葡萄糖醛酸、4-O-[（S）-1-羧乙基]-D-甘露糖和葡糖酸以等摩尔比例组成的高分子量酸性聚合物。采用化学和核磁共振技术相结合的结构分析确定，多糖由线性重复四糖单元组成，其中（R）-1-羧基亚乙基桥接β-D-葡萄糖醛酸残基的O-2和O-3位置。1H和13 C NMR共振的本地和去丙酮酸血清型3多糖的同源和异源化学位移相关方法进行了充分分配。乳酸取代的甘露吡喃糖残基和丙酮酸缩醛的绝对配置确定从1H-1H NOE测量的完整的多糖。4-O-[（S）-1-羧乙基]-β-D-吡喃甘露糖R的绝对手性的明确测定
The specific capsular polysaccharide produced by Rhodococcusequi serotype 3 was found to be a high-molecular-weight acidic polymer composed of D-glucose, D-galactose, D-glucuronic acid, 4-O-[(S)-1-carboxyethyl]-D-mannose, and pyruvic acid in equal molar proportions. Structural analysis, employing a combination of chemical and nuclear magnetic resonance techniques, established that the polysaccharide is composed of linear repeating tetrasaccharide units,in which (R)-1-carboxyethylidene groups bridge the O-2 and O-3 positions of the β-D-glucuronic acid residues. The 1H and 13C NMR resonances of the native and depyruvulated serotype 3 polysaccharides were fully assigned by homo- and heteronuclear chemical shift correlation methods. The absolute configurations of the lactate-substituted mannopyranosyl residues and the pyruvate acetals were determined from 1H–1H NOE measurements on the intact polysaccharide. Unequivocal determination of the absolute chirality of the 4-O-[(S)-1-carboxyethyl]-β-D-mannopyranose r...