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Isopeptide method: development of S-acyl isopeptide method for the synthesis of difficult sequence-containing
Taku Yoshiya1, Nui Ito, Tooru Kimura
1Department 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.
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.
