Issue 25, 2019

A chemoselective reaction between protein N-homocysteinylation and azides catalyzed by heme(ii)

Abstract

Herein, we present a serendipitously discovered chemoselective labelling of protein N-homocysteinylation with bioorthogonal azide probes. The reaction proceeds rapidly under alkaline and heating conditions. Our experiments suggest that azides can be converted to aldehydes in situ catalyzed by heme(II), followed by a condensation with protein N-homocysteinylation to afford stable 1,3-thiazines.

Graphical abstract: A chemoselective reaction between protein N-homocysteinylation and azides catalyzed by heme(ii)

Supplementary files

Article information

Article type
Communication
Submitted
03 Jan 2019
Accepted
20 Feb 2019
First published
11 Mar 2019

Chem. Commun., 2019,55, 3654-3657

A chemoselective reaction between protein N-homocysteinylation and azides catalyzed by heme(II)

N. Chen, Z. Qiao and C. Wang, Chem. Commun., 2019, 55, 3654 DOI: 10.1039/C9CC00055K

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