Issue 27, 2015

Twisted amide electrophiles enable cyclic peptide sequencing

Abstract

There is an ever-increasing interest in synthetic methods that not only enable peptide macrocyclization, but also facilitate downstream application of the synthesized molecules. We have found that aziridine amides are stereoelectronically attenuated in a macrocyclic environment such that non-specific interactions with biological nucleophiles are reduced or even shut down. The electrophilic reactivity, revealed at high pH, enables peptide sequencing by mass spectrometry, which will further broaden the utility of aziridine amide-containing libraries of macrocycles.

Graphical abstract: Twisted amide electrophiles enable cyclic peptide sequencing

Supplementary files

Article information

Article type
Communication
Submitted
24 May 2015
Accepted
28 May 2015
First published
03 Jun 2015

Org. Biomol. Chem., 2015,13, 7384-7388

Author version available

Twisted amide electrophiles enable cyclic peptide sequencing

S. Zaretsky, V. Rai, G. Gish, M. W. Forbes, M. Kofler, J. C. Y. Yu, J. Tan, J. L. Hickey, T. Pawson and A. K. Yudin, Org. Biomol. Chem., 2015, 13, 7384 DOI: 10.1039/C5OB01050K

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