The use of a cysteinyl prolyl ester (CPE) autoactivating unit in peptide ligation reactions
The use of a cysteinyl prolyl ester (CPE) autoactivating unit in peptide ligation reactions
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DOI：
10.1016/j.tet.2009.03.008
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发表时间：
2009-05-09
期刊：
影响因子：
2.1
通讯作者：
Aimoto, Saburo
中科院分区：
文献类型：
--
作者：
Kawakami, Toru;Aimoto, Saburo
在C-末端含有半胱氨酰脯氨酰酯（CPE）部分的肽（CPE肽）通过分子内N-S酰基转移反应自发转化为二酮哌嗪硫酯，随后形成二酮哌嗪。CPE肽可以在一锅法中与Cys肽连接。肽二酮哌嗪硫酯也可以通过与外部硫醇化合物如巯基乙磺酸钠的分子间硫醇-硫酯交换转化为肽硫酯。由于CPE肽需要通过标准Fmoc固相合成来制备，因此它是肽硫酯的通用替代物，提供了有望用于多肽合成的灵活连接策略。(C)2009爱思唯尔有限公司保留所有权利。
A peptide containing a cysteinyl prolyl ester (CPE) moiety at the C-terminus (CPE peptide) is spontaneously transformed into a diketopiperazine thioester via an intramolecular N-S acyl shift reaction, Followed by diketopiperazine Formation. The CPE peptide can be ligated with a Cys-peptide in a one-pot procedure. The peptide diketopiperazine thioester call also be transformed into a peptide thioester by intermolecular thiol-thioester exchange with external thiol compounds such as sodium mercaptoethanesulfonate. Since CPE peptides call be prepared by standard Fmoc solid-phase synthesis, it is a versatile alternative to the peptide thioester, providing a flexible ligation strategy that promises to be useful in polypeptide synthesis. (C) 2009 Elsevier Ltd. All rights reserved.