Hydroxynorleucine as a glycosyl acceptor is an efficient means for introducing amino acid functionality into complex carbohydrates

被引：15

作者：

Keding, SJ

Atsushi, E

Biswas, K

Zatorski, A

Coltart, DM

Danishefsky, SJ

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 16期

基金：

加拿大自然科学与工程研究理事会; 美国国家卫生研究院;

关键词：

hydroxynorleucine; glycosylation; glycosylamino acid; carbohydrate-based antitumor vaccines;

D O I：

10.1016/S0040-4039(03)00517-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to the synthesis of biologically relevant glycosyl amino acids using a non-natural amino acid as the glycosyl acceptor is described. The procedure involves a glycosylation reaction of a suitable carbohydrate donor with Fmoc-L-hydroxynorleucine benzyl ester. This reaction results in the direct incorporation of the amino acid moiety. The acceptor can be used for the preparation of alpha- or beta-O-linked glycosides depending upon the nature of the glycosyl donor. This method has been applied in the synthesis of six different tumor-associated carbohydrate antigens. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3413 / 3416

页数：4

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