Visible-light-mediated selective arylation of cysteine in batch and flow

C. Bottecchia, M. Rubens, S.B. Gunnoo, V. Hessel, A. Madder

Research output: Contribution to journalArticleAcademicpeer-review

52 Citations (Scopus)
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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.
Original languageEnglish
Pages (from-to)12702–12707
Number of pages6
JournalAngewandte Chemie - International Edition
Volume56
Issue number41
Early online date1 Sep 2017
DOIs
Publication statusPublished - 2 Oct 2017

Keywords

  • cysteine arylation
  • diazonium salts
  • microreactors
  • photochemistry
  • photoredox catalysis

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