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Epimerization-free synthesis of cyclic peptide by use of the O-acyl isopeptide method

✍ Scribed by Taku Yoshiya; Hiroyuki Kawashima; Yuka Hasegawa; Kazuhiro Okamoto; Tooru Kimura; Youhei Sohma; Yoshiaki Kiso

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
234 KB
Volume
16
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

A head‐to‐tail cyclization of a protected linear hexapeptide with a C‐terminal O‐acyl isopeptide proceeded to give a cyclic O‐acyl isopeptide without epimerization. The cyclic O‐acyl isopeptide possessed different secondary structures compared with the native cyclic peptide. The isopeptide was then efficiently converted to the desired cyclic peptide via an O‐to‐N acyl migration reaction using a silica gel‐anchored base. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd.

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