title: Synthesis of linear tripeptides for right-hand segments of complestatin.
abstract: This paper concerns a synthetic study of the right-hand segment of complestatin, an inhibitor of gp120-CD4 receptor. The effective synthesis of four important precursors for the right-hand segment of complestatin is described. Two of them are the precursor tripeptides for macrolactamization to the right-hand segment of complestatin at the last step and the other two are the precursor tripeptides for ring-closing reaction using Suzuki and Stille coupling, respectively, to the right-hand segment of complestatin at the last step. These compounds and the synthetic procedure will serve for both the synthesis of the right-hand segment and total synthesis of complestatin in the near future. In addition, consideration of the smooth acidic isomerization of complestatin to chloropeptin was carried out by density functional theory (DFT) calculation.
authors.affiliation: School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan. yamadaky@violet.plala.or.jp
authors.forename: Yaeko
authors.initials: Y
authors.lastname: Yamada
authors.forename: Ai
authors.initials: A
authors.lastname: Akiba
authors.forename: Shiho
authors.initials: S
authors.lastname: Arima
authors.forename: Chiharu
authors.initials: C
authors.lastname: Okada
authors.forename: Kiminari
authors.initials: K
authors.lastname: Yoshida
authors.forename: Fumihiro
authors.initials: F
authors.lastname: Itou
authors.forename: Toshitsugu
authors.initials: T
authors.lastname: Kai
authors.forename: Toshiko
authors.initials: T
authors.lastname: Satou
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Takeda
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Harigaya
mesh_terms: D002733:Chlorophenols / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D002733:Chlorophenols; D009842:Oligopeptides; D010456:Peptides, Cyclic; C023490:complestatin