An efficient solid‐phase synthesis of peptidyl‐N‐acetylguanidines for use in native chemical ligation

This report describes an efficient solid‐phase synthesis of peptidyl‐N‐acetylguanidines, which can be used as a peptide‐α‐thioester precursor. This new synthetic method employing selective activation and cleavage of a peptide bond successfully provided peptidyl‐N‐acetylguanidines from the on‐resin protected peptides prepared by standard Fmoc‐SPPS. The reactivity of a peptidyl‐N‐acetylguanidine in native chemical ligation was evaluated through the synthesis of glucose‐dependent insulinotropic polypeptide analogue.

Source: Journal of Peptide Science - March 21, 2016 Category: Biochemistry Authors: Ryo Okamoto, Madoka Isoe, Masayuki Izumi, Yasuhiro Kajihara Tags: Special Issue Article Source Type: research