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Isopeptide method: development of S-acyl isopeptide method for the synthesis of difficult sequence-containing peptides

✍ Scribed by Taku Yoshiya; Nui Ito; Tooru Kimura; Yoshiaki Kiso

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 143 KB
Volume: 14
Category: Article
ISSN: 1075-2617
DOI: 10.1002/psc.1053

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✦ Synopsis

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–NH~2~ 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. Copyright © 2008 European Peptide Society and John Wiley & Sons, Ltd.

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