Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags

Gergely B. Cserép, Zsuzsa Baranyai, Dávid Komáromy, Kata Horváti, Szilvia Bosze, Péter Kele

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Fluorescent tagging of Cys-containing peptides is presented herein. The procedure follows a two-step sequential reaction scheme using thiol specific bifunctional chemical reporters and fluorogenic labels. Vinyl-sulfone bearing chemical reporters have been synthesized and demonstrated to selectively modify cysteine under physiological conditions in the presence of other nucleophilic amino acids. Bifunctional chemical reporters decorated with a terminal alkyne moiety, suitable for modification with azide containing fluorogenic labels were also synthesized. Such fluorogenic (turn on) labels in combination with these new vinyl-sulfone tags can be used generally in fluorescent modulation schemes of thiol-bearing biomolecules.

Original languageEnglish
Pages (from-to)5961-5965
Number of pages5
JournalTetrahedron
Volume70
Issue number35
DOIs
Publication statusPublished - Sep 2 2014

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Keywords

  • Bioorthogonal tagging
  • Fluorescence
  • Fluorogenic dyes
  • Thiol-ene chemistry
  • Vinyl-sulfones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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