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

被引：13

作者：

Yoshiya, Taku ^{[1
]}

Kawashima, Hiroyuki ^{[1
]}

Hasegawa, Yuka ^{[1
]}

Okamoto, Kazuhiro ^{[1
]}

Kimura, Tooru ^{[1
]}

Sohma, Youhei ^{[1
]}

Kiso, Yoshiaki ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Dept Med Chem, Ctr Frontier Res Med Sci, Yamashina Ku, Kyoto 6078412, Japan

来源：

JOURNAL OF PEPTIDE SCIENCE | 2010年 / 16卷 / 08期

关键词：

racemization; cyclic peptide; isopeptide; epimerization; O-to-N acyl migration; SWITCH-PEPTIDES; DEPSIPEPTIDE TECHNIQUE; SEGMENT CONDENSATION; HEXAPEPTIDE ANALOG; SOMATOSTATIN; MIGRATION; A-BETA-1-42; CYCLIZATION; ACTIVATION; SEQUENCES;

D O I：

10.1002/psc.1261

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 (C) 2010 European Peptide Society and John Wiley & Sons, Ltd.

引用

页码：437 / 442

页数：6

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