title: Isopeptide method: development of S-acyl isopeptide method for the synthesis of difficult sequence-containing peptides.
abstract: A novel strategy for a more efficient synthesis of difficult sequence-containing peptides, the S-acyl isopeptide method, was developed and successfully applied. A model pentapeptide Ac-Val-Val-Cys-Val-Val-NH2 was synthesized via its water-soluble S-acyl isopeptide using an S-acyl isodipeptide unit, Boc-Cys(Fmoc-Val)-OH. An S-acyl isopeptide possessing excellent water solubility could be readily and quantitatively converted to the native peptide via an S--N intramolecular acyl migration reaction at pH 7.4. Thus, the S-acyl isopeptide method provides a useful tool in peptide chemistry.
authors.affiliation: Department of Medicinal Chemistry, Division of Medicinal Chemical Sciences, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Japan.
authors.forename: Taku
authors.initials: T
authors.lastname: Yoshiya
authors.forename: Nui
authors.initials: N
authors.lastname: Ito
authors.forename: Tooru
authors.initials: T
authors.lastname: Kimura
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Kiso
mesh_terms: D000595:Amino Acid Sequence; D002219:Carbamates / Q000737:chemistry; D002621:Chemistry / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D012995:Solubility
chemical_list: D002219:Carbamates; D010446:Peptide Fragments; D010455:Peptides; D003545:Cysteine; D005459:Fluorides