[由肺炎链球菌荚膜多糖合成三糖单元]

[Synthesis of trisaccharide units from capsular polysaccharides of Streptococcus pneumoniae].

作者信息

Paulsen H, Helpap B, Lorentzen J P

机构信息

Institut für Organische Chemie, Universität Hamburg, 13 Bundesrepublik Deutschland.

出版信息

Carbohydr Res. 1988 Aug 15;179:173-97. doi: 10.1016/0008-6215(88)84117-x.

DOI:10.1016/0008-6215(88)84117-x

PMID:3208246

Abstract

In the presence of silver silicate as promoter, the reaction of glycosyl bromide of 2-azido-2-deoxy-D-mannose with 1,6-anhydro-2,3-di-O-benzyl-beta-D- glucopyranose led to derivatives of the disaccharide beta-D-ManpNac-(1----4)-D- Glcp. The derivatives were activated into disaccharide halides and employed as glycosyl donors in block synthesis. By chain extension with L-rhamnose and D-glucose, four trisaccharides were synthesized. They represent components of capsular polysaccharide "repeating units" of various Streptococcus pneumoniae types, beta-D-Man-pNAc-(1----4)-alpha-D-Glcp-(1----2)-L-Rhap (type 19 F), beta-D-ManpNAc-(1----4)-alpha-D-Glcp-(1----3)-L-Rhap (type 19 A), beta-D-ManpNAc-(1----4)-alpha-D-Glcp-(1----4)-D-Glcp (type 9 A), and beta-D-ManpNAc-(1----4)-beta-D-Glcp-(1----4)-D-Glcp (type 9 V).

摘要

在硅酸银作为促进剂存在的情况下，2-叠氮基-2-脱氧-D-甘露糖的糖基溴与1,6-脱水-2,3-二-O-苄基-β-D-吡喃葡萄糖反应生成二糖β-D-ManpNac-(1→4)-D-Glcp的衍生物。这些衍生物被活化成二糖卤化物，并用作逐步合成中的糖基供体。通过与L-鼠李糖和D-葡萄糖进行链延长反应，合成了四种三糖。它们代表了各种肺炎链球菌类型的荚膜多糖“重复单元”的组成部分，β-D-Man-pNAc-(1→4)-α-D-Glcp-(1→2)-L-Rhap（19F型），β-D-ManpNAc-(1→4)-α-D-Glcp-(1→3)-L-Rhap（19A型），β-D-ManpNAc-(1→4)-α-D-Glcp-(1→4)-D-Glcp（9A型），以及β-D-ManpNAc-(1→4)-β-D-Glcp-(1→4)-D-Glcp（9V型）。