Facile Preparation of Peptides with C-Terminal N-Alkylamide via Radical-Initiated Dethiocarboxylation

Tatsuhiko Shimizu; Rin Miyajima; Naoto Naruse; Kosuke Yamaoka; Keisuke Aihara; Akira Shigenaga; Akira Otaka

doi:10.1248/cpb.c15-01025

Notes

Facile Preparation of Peptides with C-Terminal N-Alkylamide via Radical-Initiated Dethiocarboxylation

Tatsuhiko Shimizu, Rin Miyajima, Naoto Naruse, Kosuke Yamaoka, Keisuke Aihara, Akira Shigenaga, Akira Otaka

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Keywords: C-terminal N-alkylamide, peptide thioacid, dethiocarboxylation

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Supplementary material

2016 Volume 64 Issue 4 Pages 375-378

DOI https://doi.org/10.1248/cpb.c15-01025

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Abstract

A new synthetic method has been developed to prepare peptides bearing a C-terminal N-alkylamide from peptide thioacids via a radical-initiated dethiocarboxylation process. This method enables the introduction of various alkyl groups to C-terminal amides simply by replacing the amino acid building block. Its application to the preparation of anti-cancer drug ABT-510 is also reported.

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