大肠杆菌LP 1092荚膜多糖交替线性和支链重复单元的合成，该多糖含有与D-核糖二级位置相连的3-脱氧-α-D-甘露-2-辛酮糖酸（KDO）。

Synthesis of alternate linear and branched repeating units of the Escherichia coli LP 1092 capsular polysaccharide containing 3-deoxy-alpha-D-manno-2-octulosonic acid (KDO) linked to secondary positions of D-ribose.

作者信息

Kosma P, Christian R, Schulz G, Unger F M

出版信息

Carbohydr Res. 1985 Sep 1;141(2):239-53. doi: 10.1016/s0008-6215(00)90455-5.

Abstract

The oligosaccharides, methyl 3-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-beta-D-ribofuranosid e, methyl 2-O-beta-D-ribofuranosyl-3-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-beta-D-ribofuranosid e, and methyl O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2----2)-O-beta-D- ribofuranosyl-(1----2)-beta-D-ribofuranoside were prepared in high purity and good over-all yields. The constitutions of the trisaccharide derivatives correspond to the repeating units of the proposed linear and branched structures of the capsular polysaccharide(s) from Escherichia coli LP 1092. The alpha-KDO-(2----3)-beta-D-Ribf and alpha-KDO-(2----2)-beta-D-Ribf units were synthesized by a modification of the Helferich procedure using methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-alpha-D-manno-2-octulopyranosyl bromide)-onate and appropriate beta-D-ribofuranosyl derivatives. The constitutional and configurational assignments were based on the 250-MHz 1H-n.m.r.-spectra of protected derivatives of the oligosaccharides.

摘要

制备了低聚糖3 - O -（3 - 脱氧 - α - D - 甘露 - 2 - 辛吡喃糖醛酸钠） - β - D - 呋喃核糖苷、2 - O - β - D - 呋喃核糖基 - 3 - O -（3 - 脱氧 - α - D - 甘露 - 2 - 辛吡喃糖醛酸钠） - β - D - 呋喃核糖苷和O -（3 - 脱氧 - α - D - 甘露 - 2 - 辛吡喃糖醛酸钠） -（2→2） - O - β - D - 呋喃核糖基 -（1→2） - β - D - 呋喃核糖苷，其纯度高，总产率良好。三糖衍生物的结构与来自大肠杆菌LP 1092的荚膜多糖所提出的线性和分支结构的重复单元相对应。α - KDO -（2→3） - β - D - Ribf和α - KDO -（2→2） - β - D - Ribf单元是通过对Helferich方法进行改进合成的，使用（4,5,7,8 - 四 - O - 乙酰基 - 3 - 脱氧 - α - D - 甘露 - 2 - 辛吡喃糖基溴） - 甲酸盐和适当的β - D - 呋喃核糖基衍生物。结构和构型归属基于低聚糖保护衍生物的250 - MHz 1H - NMR光谱。