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Visible-Light-Mediated Selective Arylation of Cysteine in Batch and Flow.

ABSTRACT: 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.

SUBMITTER: Bottecchia C

PROVIDER: S-EPMC5656832 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Visible-Light-Mediated Selective Arylation of Cysteine in Batch and Flow.

Bottecchia Cecilia C Rubens Maarten M Gunnoo Smita B SB Hessel Volker V Madder Annemieke A Noël Timothy T

Angewandte Chemie (International ed. in English) 20170901 41

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. Moreo ...[more]

PMID: 28805276

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