Epimerization‐free synthesis of cyclic peptide by use of the O‐acyl isopeptide method |
| |
| Authors: | Taku Yoshiya Hiroyuki Kawashima Yuka Hasegawa Kazuhiro Okamoto Tooru Kimura Youhei Sohma Yoshiaki Kiso |
| |
| Affiliation: | Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412, Japan |
| |
| 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. |
| |
| Keywords: | racemization cyclic peptide isopeptide epimerization O‐to‐N acyl migration |
|
