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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Published inAngewandte Chemie Vol. 129; no. 41; pp. 12876 - 12881
Main Authors Bottecchia, Cecilia, Rubens, Maarten, Gunnoo, Smita B., Hessel, Volker, Madder, Annemieke, Noël, Timothy
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 02.10.2017
Subjects
Biocompatibility
Buffers
Chemistry
Cysteinarylierung
Cysteine
Diazoniumsalze
Mikroreaktoren
Phosphates
Photochemie
Photoredoxkatalyse
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. Chemische Modifizierung von Peptiden: Die durch sichtbares Licht herbeigeführte Cystein‐Arylierung basiert auf der Verwendung von Eosin‐Y als metallfreiem Photokatalysator und Aryldiazoniumsalzen als arylierende Agenzien. Die Batch‐ und Flow‐Verfahren liefern eine Reihe arylierter Cysteinderivate und arylierter cysteinhaltiger Dipeptide.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201706700