一种新型硫酯化反应在通过改良硫酯法合成趋化因子CCL27中的应用。

Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method.

作者信息

Hojo Hironobu, Murasawa Yuichi, Katayama Hidekazu, Ohira Tsuyoshi, Nakahara Yuko, Nakahara Yoshiaki

机构信息

Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Hiratsuka, Kanagawa 259-1292, Japan.

出版信息

Org Biomol Chem. 2008 May 21;6(10):1808-13. doi: 10.1039/b800884a. Epub 2008 Mar 31.

DOI:10.1039/b800884a

PMID:18452017

Abstract

Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag(+)-free thioester method.

摘要

通过传统的9-芴甲氧羰基（Fmoc）策略，利用新型N-烷基半胱氨酸（NAC）辅助硫酯化反应制备了肽段的芳基硫酯。在其C末端带有NAC的肽通过Fmoc策略制备，并通过4-巯基苯乙酸（MPAA）处理转化为芳基硫酯，且无明显副反应。该肽硫酯用于通过无银硫酯法高效制备95个氨基酸（AA）的趋化因子CCL27。