Semisynthesis of membrane-anchored cholesteryl lipoproteins on live cell surface by azide-alkyne click reaction

Balázs Schäfer, Erika Orbán, Gabriella Fiser, Annamária Marton, C. Vízler, C. Tömböly

Research output: Contribution to journalArticle

Abstract

Cholesteryl lipoprotein semisynthesis was accomplished via a copper-catalyzed azide-alkyne cycloaddition on the surface of live cells. In this convergent synthesis an azido-cholesterol was introduced into the cell membrane without the application of detergents followed by conjugation of the C-terminal alkyne modified protein. This cytocompatible method resulted in a folded membrane-anchored protein containing a small molecule fluorophore in the lipid headgroup.

Original languageEnglish
Pages (from-to)868-873
Number of pages6
JournalTetrahedron Letters
Volume57
Issue number8
DOIs
Publication statusPublished - Feb 24 2016

Fingerprint

Alkynes
Azides
Lipoproteins
Membranes
Cycloaddition
Fluorophores
Cycloaddition Reaction
Cell membranes
Detergents
Copper
Membrane Proteins
Proteins
Cholesterol
Cell Membrane
Lipids
Molecules

Keywords

  • Bioconjugation
  • Cell surface
  • Cholesterol
  • Click reaction
  • Lipoprotein

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Semisynthesis of membrane-anchored cholesteryl lipoproteins on live cell surface by azide-alkyne click reaction. / Schäfer, Balázs; Orbán, Erika; Fiser, Gabriella; Marton, Annamária; Vízler, C.; Tömböly, C.

In: Tetrahedron Letters, Vol. 57, No. 8, 24.02.2016, p. 868-873.

Research output: Contribution to journalArticle

Schäfer, Balázs ; Orbán, Erika ; Fiser, Gabriella ; Marton, Annamária ; Vízler, C. ; Tömböly, C. / Semisynthesis of membrane-anchored cholesteryl lipoproteins on live cell surface by azide-alkyne click reaction. In: Tetrahedron Letters. 2016 ; Vol. 57, No. 8. pp. 868-873.
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