Improved acidolytic deprotection conditions for the Fmoc-based solid-phase synthesis of thioxo peptides

被引：10

作者：

Miwa, JH ^{[1
]}

Margarida, LA ^{[1
]}

Meyer, AE ^{[1
]}

机构：

[1] Wellesley Coll, Dept Chem, Wellesley, MA 02481 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 41期

关键词：

thioxo peptide; thioamide; solid-phase peptide synthesis; thiazolone;

D O I：

10.1016/S0040-4039(01)01500-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acid-mediated cleavage of a synthetic thioxo peptide was monitored using deprotection cocktails with varying concentrations of TFA. Thioxo peptides are acid labile, undergoing cleavage at the amide linkage immediately following the thioamide linkage in the sequence, This acid lability makes Fmoc-based synthesis the method of choice for thioxo peptide preparation. The extent of cleavage increases with increased TFA concentration and longer reaction time. Data presented herein indicate that deprotection protocols involving low TFA concentration (ca. 80%) and short reaction times (ca. 2 h) minimize the losses due to acidolytic cleavage. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7189 / 7191

页数：3

共 8 条

[1]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[2] Endothiopeptides alias peptide thioamides: Review [J].