Construction of carbohydrate-based antitumor vaccines: synthesis of glycosyl amino acids by olefin cross-metathesis

被引：37

作者：

Biswas, K

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 | 2002年 / 43卷 / 35期

基金：

美国国家卫生研究院; 加拿大自然科学与工程研究理事会;

关键词：

glycosyl amino acids; cross-metathesis; allyl glycosides; carbohydrate-based antitumor vaccines;

D O I：

10.1016/S0040-4039(02)01336-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of biologically relevant glycosyl amino acids from corresponding O-allyl glycosides is described. The procedure involves a cross-meta thesis reaction with Fmoc-L-allylglycine benzyl ester, followed by reduction of the resulting olefin via catalytic hydrogenation, with the concomitant release of the free acid. This method has also been applied to the breast and prostate cancer antigen Globo-H, to afford a hexasaccharide glycosyl amino acid that has been previously incorporated in a polyvalent antitumor vaccine. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：6107 / 6110

页数：4

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