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

Fingerprint

Bearings (structural)
Sulfhydryl Compounds
Labels
Peptides
Alkynes
Azides
Cysteine
Biomolecules
Amino Acids
Modulation
divinyl sulfone

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags. / Cserép, Gergely B.; Baranyai, Zsuzsa; Komáromy, Dávid; Horváti, Kata; Bosze, Szilvia; Kele, Péter.

In: Tetrahedron, Vol. 70, No. 35, 02.09.2014, p. 5961-5965.

Research output: Contribution to journalArticle

Cserép, Gergely B. ; Baranyai, Zsuzsa ; Komáromy, Dávid ; Horváti, Kata ; Bosze, Szilvia ; Kele, Péter. / Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags. In: Tetrahedron. 2014 ; Vol. 70, No. 35. pp. 5961-5965.
@article{ea6c272f2e774a48a68eef7ae5fd234f,
title = "Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags",
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.",
keywords = "Bioorthogonal tagging, Fluorescence, Fluorogenic dyes, Thiol-ene chemistry, Vinyl-sulfones",
author = "Cser{\'e}p, {Gergely B.} and Zsuzsa Baranyai and D{\'a}vid Kom{\'a}romy and Kata Horv{\'a}ti and Szilvia Bosze and P{\'e}ter Kele",
year = "2014",
month = "9",
day = "2",
doi = "10.1016/j.tet.2014.05.103",
language = "English",
volume = "70",
pages = "5961--5965",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "35",

}

TY - JOUR

T1 - Fluorogenic tagging of peptides via Cys residues using thiol-specific vinyl sulfone affinity tags

AU - Cserép, Gergely B.

AU - Baranyai, Zsuzsa

AU - Komáromy, Dávid

AU - Horváti, Kata

AU - Bosze, Szilvia

AU - Kele, Péter

PY - 2014/9/2

Y1 - 2014/9/2

N2 - 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.

AB - 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.

KW - Bioorthogonal tagging

KW - Fluorescence

KW - Fluorogenic dyes

KW - Thiol-ene chemistry

KW - Vinyl-sulfones

UR - http://www.scopus.com/inward/record.url?scp=84949116500&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84949116500&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.05.103

DO - 10.1016/j.tet.2014.05.103

M3 - Article

AN - SCOPUS:84949116500

VL - 70

SP - 5961

EP - 5965

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 35

ER -