Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens

被引：24

作者：

Keding, SJ

Endo, A

Danishefsky, SJ

机构：

[1] Mem 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 | 2003年 / 59卷 / 35期

基金：

美国国家卫生研究院;

关键词：

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

D O I：

10.1016/S0040-4020(03)00935-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of biologically relevant glycosylamino acids using a non-natural amino acid as the glycosyl acceptor is described. The glycosylation reaction of a monosaccharide tri-chloroacetimidate donor with Fmoc-L-hydroxynorleucine benzyl ester provided the alpha-O-linked product. Conversely, when the glycosylation reaction was carried out with a glycal epoxide donor, the beta-O-linked product predominated. We have used these two complementary glycosylation reactions to synthesize five different glycosylamino acids, each containing the Tn. TF, STn, Lewis(y) or Globo-H tumor-associated carbohydrate antigens. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7023 / 7031

页数：9

共 27 条

[1] Pursuit of optimal carbohydrate-based anticancer vaccines:: Preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewisy antigens [J].