与9A&L型、9N型和9A型肺炎链球菌荚膜多糖相对应的四糖和五糖的合成

Synthesis of tetra- and pentasaccharides corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 9A&L, 9N and 9A.

作者信息

Alpe Mia, Oscarson Stefan

机构信息

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden.

出版信息

Carbohydr Res. 2003 Nov 14;338(23):2605-9. doi: 10.1016/s0008-6215(03)00271-4.

DOI:10.1016/s0008-6215(03)00271-4

PMID:14670720

Abstract

Two tetrasaccharides, alpha-D-GlcAp-(1-->3)-alpha-D-Galp-(1-->3)-beta-D-ManpNAc-(1-->4)-beta-D-Glcp and alpha-D-GlcAp-(1-->3)-alpha-D-Glcp-(1-->3)-beta-D-ManpNAc-(1-->4)-beta-D-Glcp (protected form), and a pentasaccharide, alpha-D-Glcp-(1-->4)-alpha-D-GlcAp-(1-->3)-alpha-D-Galp-(1-->3)-beta-D-ManpNAc-(1-->4)-beta-D-Glcp have been synthesised from 2-aminoethyl glycoside trisaccharide acceptors in a linear approach via consecutive alpha-glycosylations. Ethyl thioglycosides were used as glycosyl donors and DMTST in Et(2)O or NIS/TfOH in CH(2)Cl(2) were employed as promoters.

摘要

通过连续的α-糖基化反应，以线性方式从2-氨基乙基糖苷三糖受体合成了两种四糖，即α-D-葡萄糖醛酸-(1→3)-α-D-半乳糖-(1→3)-β-D-甘露糖胺-(1→4)-β-D-葡萄糖和α-D-葡萄糖醛酸-(1→3)-α-D-葡萄糖-(1→3)-β-D-甘露糖胺-(1→4)-β-D-葡萄糖（保护形式），以及一种五糖，即α-D-葡萄糖-(1→4)-α-D-葡萄糖醛酸-(1→3)-α-D-半乳糖-(1→3)-β-D-甘露糖胺-(1→4)-β-D-葡萄糖。乙基硫代糖苷用作糖基供体，二甲基(2,4,6-三甲氧基苯)锍四氟硼酸盐在二乙醚中或N-碘代琥珀酰亚胺/三氟甲磺酸在二氯甲烷中用作促进剂。