Visible‐Light‐Mediated Selective Arylation of Cysteine in Batch and Flow

A mild visible‐light‐mediated strategy for cysteine arylation is presented. The method relies on the use of eosin Y as a metal‐free photocatalyst and aryldiazonium salts as arylating agents. The reaction can be significantly accelerated in a microflow reactor, whilst allowing the in situ formation o...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-10, Vol.56 (41), p.12702-12707
Main Authors: Bottecchia, Cecilia, Rubens, Maarten, Gunnoo, Smita B., Hessel, Volker, Madder, Annemieke, Noël, Timothy
Format: Article
Language:English
Subjects:
Biocompatibility
Buffers
Communication
Communications
Cysteine
cysteine arylation
diazonium salts
microreactors
Phosphates
photochemistry
photoredox catalysis
Reaction time
Salts
Yttrium
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Summary:A mild visible‐light‐mediated strategy for cysteine arylation is presented. The method relies on the use of eosin Y as a metal‐free photocatalyst and aryldiazonium salts as arylating agents. The reaction can be significantly accelerated in a microflow reactor, whilst allowing the in situ formation of the required diazonium salts. The batch and flow protocol described herein can be applied to obtain a broad series of arylated cysteine derivatives and arylated cysteine‐containing dipeptides. Moreover, the method was applied to the chemoselective arylation of a model peptide in biocompatible reaction conditions (room temperature, phosphate‐buffered saline (PBS) buffer) within a short reaction time. Chemical modifications of peptides: The mild visible‐light‐mediated arylation of cysteine relies on the use of eosin Y as a metal‐free photocatalyst and aryldiazonium salts as arylating agents. The batch and flow method afforded a series of arylated cysteine derivatives and arylated cysteine‐containing dipeptides. A model peptide has been chemoselectively arylated under biocompatible reaction conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201706700