Tyrosine specific sequential labeling of proteins

Gergely B. Cserép, András Herner, Otto S. Wolfbeis, P. Kele

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

We report (a) on the synthesis of a long-wavelength fluorescent coumarin containing an allyloxy acetate moiety, (b) the synthesis of two linkers containing an allyloxy acetate and an alkyne or azide function, respectively, and (c) the selective modification human serum albumin by a sequential method involving Pd(II) catalyzed modification of the phenolic side chain of tyrosine residues with an alkyne bearing linker and a subsequent azide-alkyne click reaction with an azide functionalized long-wavelength emitting coumarin dye. The method is likely to be applicable to various kinds of azido-modified fluorophores, and the Pd(II)-catalyzed modification of the tyrosines may also be used to introduce other kinds of tags. With these reagents, tyrosine specific modulation of proteins and peptides becomes possible either directly or in a sequential manner.

Original languageEnglish
Pages (from-to)5776-5778
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number21
DOIs
Publication statusPublished - Nov 1 2013

Fingerprint

Alkynes
Azides
Labeling
Tyrosine
Acetates
Bearings (structural)
Wavelength
Proteins
Fluorophores
Serum Albumin
Coloring Agents
Modulation
Peptides
coumarin

Keywords

  • Bioorthogonal chemistry
  • Chemical reporter
  • Click chemistry
  • Sequential labeling
  • Tyrosine tagging

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Tyrosine specific sequential labeling of proteins. / Cserép, Gergely B.; Herner, András; Wolfbeis, Otto S.; Kele, P.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 21, 01.11.2013, p. 5776-5778.

Research output: Contribution to journalArticle

Cserép, Gergely B. ; Herner, András ; Wolfbeis, Otto S. ; Kele, P. / Tyrosine specific sequential labeling of proteins. In: Bioorganic and Medicinal Chemistry Letters. 2013 ; Vol. 23, No. 21. pp. 5776-5778.
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