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

Author information

Tatsuhiko Shimizu
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University
Rin Miyajima
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University
Naoto Naruse
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University
Kosuke Yamaoka
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University
Keisuke Aihara
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University
Akira Shigenaga
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University
Akira Otaka Corresponding author
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University

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

Details

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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Corresponding author

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