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

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.

• Authors: Tatsuhiko Shimizu, Rin Miyajima, Naoto Naruse, Kosuke Yamaoka, Keisuke Aihara, Akira Shigenaga, Akira Otaka
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 64 Issue 4 Pg. 375-8 ( 2016) ISSN: 1347-5223 [Electronic] Japan
• PMID: 27039836 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Carboxylic Acids
• Peptides

Topics

• Amides (chemistry)
• Carboxylic Acids (chemistry)
• Chromatography, High Pressure Liquid
• Peptides (chemistry)