Work

An Umpolung Approach for the Chemoselective Arylation of Selenocysteine in Unprotected Peptides

Year: 2015

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5b05447

Authors: Daniel T. Cohen, Chi Zhang, Bradley L. Pentelute, Stephen L. Buchwald

Institution: Massachusetts Institute of Technology

Language: English

Topic: Organoselenium and organotellurium chemistry

Subfield: Toxicology

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500