Donor-bound glycosylation for various glycosyl acceptors: Bidirectional solid-phase semisynthesis of vancomycin and its derivatives

被引：18

作者：

Doi, Takayuki ^{[1
]}

Kinbara, Atsushi ^{[1
]}

Inoue, Hitoshi ^{[1
]}

Takahashi, Takashi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2007年 / 2卷 / 01期

关键词：

antibiotics; glycopeptides; glycosylation; solid-phase synthesis; vancomycin;

D O I：

10.1002/asia.200600301

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The glycosidation of a polymer-supported glycosyl donor, N-phenyltrifluoroacetimidate, with various glycosyl acceptors is reported. The application of the polymer-supported N-phenyltrifluoroacetimidate is demonstrated in the synthesis of vancomycin derivatives. 2-O-[2-(azidomethyl)benzoyl]glycosyl imidate was attached to a polymer support at the 6-position by a phenylsulfonate linked with a C13 alkyl spacer. Solid-phase glycosidation with a vancomycin aglycon, selective deprotection of the 2-(azidomethyl)benzoyl group, and glycosylation of the resulting 2-hydroxy group with a vancosamine unit were performed. Nucleophilic cleavage from the polymer support with acetate, chloride, azido, and thioacetate ions provided vancomycin derivatives in pure form after simple purification. The semisynthesis of vancomycin was achieved by deprotection of the acetate derivative.

引用

页码：188 / 198

页数：11

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