Study on systematizing the synthesis of the a-series ganglioside glycans GT1a, GD1a, and GM1 using the newly developed N-Troc-protected GM3 and GalN intermediates

被引：14

作者：

Komori, Tatsuya ^{[1
]}

Imamura, Akihiro ^{[1
,2
]}

Ando, Hiromune ^{[1
,2
]}

Ishida, Hideharu ^{[1
]}

Kiso, Makoto ^{[1
,2
]}

机构：

[1] Gifu Univ, Fac Appl Biol Sci, Dept Appl Bioorgan Chem, Gifu 5011193, Japan

[2] Kyoto Univ, Inst Integrated Cell Mat Sci ICeMS, Sakyo Ku, Kyoto 6068501, Japan

来源：

CARBOHYDRATE RESEARCH | 2009年 / 344卷 / 12期

关键词：

a-Series ganglioside; Troc group; GM3 acceptor and GM2 acceptor; Diethylphosphite method; Trichloroacetimidate method; FACILE TOTAL SYNTHESIS; EFFICIENT SYNTHESIS; LEWIS-X; GM(1); GQ1B; SIALYLATION; DERIVATIVES; ANALOGS; ANTIGEN; DESIGN;

D O I：

10.1016/j.carres.2009.06.009

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A first systematic synthesis of the glycan parts of the a-series gangliosides (GT1a, GD1a, and GM1) utilizing the newly developed N-Troc-protected GM3 and galactosaminyl building blocks is described. The key processes, including the assembly of the GM2 sequence and its conversion into the 3-hydroxy acceptor, were facilitated mainly by the high degree of participation and chemoselective cleavability of the Troc group in the galactosaminyl unit. Furthermore, the novel GM2 acceptor served as a good coupling partner during glycosylation with galactosyl, sialyl galactosyl, and disialyl galactosyl donors, successfully producing the GM1, GD1a, and GT1a glycans. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1453 / 1463

页数：11

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