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

Author:
ChenThese authors contributed equally to this work., Nan, Qiao, Zeyu, Wang, Chu
Source:
Chemical communications 2019 v.55 no.25 pp. 3654-3657
ISSN:
1364-548X
Subject:
aldehydes, azides, chemical reactions, chemoselectivity, heme
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.
Agid:
6345066