An Umpolung Approach for the Chemoselective Arylation of Selenocysteine in Unprotected Peptides
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Author(s)
Cohen, Daniel Tzvi
Zhang, Chi
Pentelute, Bradley L.
Buchwald, Stephen Leffler
Date Issued
July 2015
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Cohen, Daniel T. et al. “An Umpolung Approach for the Chemoselective Arylation of Selenocysteine in Unprotected Peptides.” Journal of the American Chemical Society 137, 31 (July 2015): 9784–9787 © 2015 American Chemical Society
Version
Final published version
Abstract
Herein we report an umpolung strategy for the bioconjugation of selenocysteine in unprotected peptides. This mild and operationally simple approach takes advantage of the electrophilic character of an oxidized selenocysteine (Se-S bond) to react with a nucleophilic arylboronic acid to provide the arylated selenocysteine within hours. This reaction is amenable to a wide range of boronic acids with different biorelevant functional groups and is unique to selenocysteine. Experimental evidence indicates that under oxidative conditions the arylated derivatives are more stable than the corresponding alkylated selenocysteine.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/JACS.5B05447
