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