使用2-氯三苯甲基树脂进行无消旋化的C端半胱氨酸肽合成。

Racemization-free synthesis of C-terminal cysteine-peptide using 2-chlorotrityl resin.

作者信息

Fujiwara Y, Akaji K, Kiso Y

机构信息

Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1994 Mar;42(3):724-6. doi: 10.1248/cpb.42.724.

DOI:10.1248/cpb.42.724

PMID:8004723

Abstract

We investigated the effects of bases, resins, and S-protecting groups on the extent of racemization at the C-terminal cysteine during Fmoc-based(Fmoc=fluoren-9-yl-methoxy-carbonyl) solid phase peptide synthesis. The use of 2-chlorotrityl resin was most effective in suppressing the racemization caused by the base treatment for Fmoc-cleavage. Somatostatin was successfully synthesized with practically no racemization using 2-chlorotrityl resin by Fmoc-chemistry.

摘要

我们研究了在基于芴甲氧羰基（Fmoc）的固相肽合成过程中，碱、树脂和S-保护基团对C端半胱氨酸消旋程度的影响。对于Fmoc脱保护的碱处理所引起的消旋，使用2-氯三苯甲基树脂在抑制消旋方面最为有效。通过Fmoc化学法，使用2-氯三苯甲基树脂成功合成了几乎没有消旋的生长抑素。