用于糖胺聚糖模块化组装的艾杜糖醛酸构建块的合成。

Synthesis of iduronic acid building blocks for the modular assembly of glycosaminoglycans.

作者信息

Lohman Gregory J S, Hunt Diana K, Högermeier Jens A, Seeberger Peter H

机构信息

Massachusetts Institute of Technology, 77 Massachusetts Avenue 18-292, Cambridge, Massachusetts 02139, USA.

出版信息

J Org Chem. 2003 Sep 19;68(19):7559-61. doi: 10.1021/jo0340760.

DOI:10.1021/jo0340760

PMID:12968922

Abstract

The modular synthesis of glycosaminoglycans requires straightforward methods for the production of large quantities of protected uronic acid building blocks. In particular, the preparation of fully differentiated iduronic acids has proven particularly challenging. An efficient route to methyl 3-O-benzyl-1,2-O-isopropylidene-alpha-l-idopyranosiduronate 6 from diacetone glucose in nine steps and 36% overall yield is described. Idopyranosiduronate 6 is useful as a glycosyl acceptor and as an intermediate that may be further elaborated into iduronic acid trichloroacetimidate glycosyl donors for the assembly of glycosaminoglycan structures as illustrated here.

摘要

糖胺聚糖的模块化合成需要直接的方法来大量生产受保护的糖醛酸构建单元。特别是，制备完全差异化的艾杜糖醛酸已被证明具有特别的挑战性。本文描述了一条从双丙酮葡萄糖出发，经过九步反应，总产率为36%，高效合成3-O-苄基-1,2-O-异亚丙基-α-L-艾杜吡喃糖醛酸甲酯6的路线。艾杜吡喃糖醛酸甲酯6可用作糖基受体和中间体，可进一步转化为艾杜糖醛酸三氯乙酰亚胺酯糖基供体，用于组装糖胺聚糖结构，如下所示。