与布氏锥虫糖基磷脂酰肌醇（GPI）锚相关的辛基O-糖苷和S-糖苷的合成及其在体外被锥虫α-半乳糖基转移酶进行的半乳糖基化反应

Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal alpha-galactosyltransferases.

作者信息

Ziegler T, Dettmann R, Duszenko M, Kolb V

机构信息

Institute of Organic Chemistry, University of Cologne, Germany.

出版信息

Carbohydr Res. 1996 Dec 13;295:7-23. doi: 10.1016/s0008-6215(96)90114-7.

DOI:10.1016/s0008-6215(96)90114-7

PMID:9002182

Abstract

Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1, 3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MITat 1.4, MITat 1.2, and MITat 1.5, respectively.

摘要

通过对2-O-苯甲酰基-4,6-O-(1,1,3,3-四异丙基-1,3-二硅氧烷-1,3-二基)-α-D-甘露吡喃糖苷的辛基O-和S-糖苷进行区域选择性原脱硅和糖脱硅反应，制备了与布氏锥虫GPI锚定核心结构α-D-Manp-(1→2)-α-D-Manp-(1→6)-α-D-Manp相关的单糖至三糖的辛基O-和S-糖苷。合成的糖类已分别用作布氏锥虫427株变体MITat 1.4、MITat 1.2和MITat 1.5血流形式膜部分进行酶促α-半乳糖基化反应的底物。