通过噻唑烷上的 N-S 酰基转移反应实现肽硫酯的串联硫醇开关合成。

Tandem thiol switch synthesis of peptide thioesters via N-S acyl shift on thiazolidine.

机构信息

School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore 637551.

出版信息

Org Lett. 2011 Oct 7;13(19):5176-9. doi: 10.1021/ol202047q. Epub 2011 Sep 8.

DOI:10.1021/ol202047q

PMID:21902201

Abstract

An efficient "thiol switch" approach for the synthesis of peptide thioesters via an acid-catalyzed N-S acyl shift and a thioester exchange reaction in tandem with concurrent removal of protecting groups is described. This method employs novel 2-(thiomethyl)thiazolidine (TMT)-anchored resins and is fully compatible with Fmoc chemistry.

摘要

描述了一种通过酸催化的 N-S 酰基转移和硫酯交换反应串联进行，并同时去除保护基团的高效“巯基开关”方法，用于合成肽硫酯。该方法采用新型 2-（巯甲基）噻唑烷（TMT）锚固树脂，完全兼容 Fmoc 化学。