Epimerization-free synthesis of cyclic peptide by use of the O-acyl isopeptide method.
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.
Yoshiya
Taku
T
Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.
Kawashima
Hiroyuki
H
Hasegawa
Yuka
Y
Okamoto
Kazuhiro
K
Kimura
Tooru
T
Sohma
Youhei
Y
Kiso
Yoshiaki
Y
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010446:Peptide Fragments / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010446:Peptide Fragments; D010456:Peptides, Cyclic