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

[Display omitted] 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 conjugati...

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Bibliographic Details
Published in:Tetrahedron letters 2016-02, Vol.57 (8), p.868-873
Main Authors: Schäfer, Balázs, Orbán, Erika, Fiser, Gabriella, Marton, Annamária, Vizler, Csaba, Tömböly, Csaba
Format: Article
Language:English
Subjects:
Alkynes
Bioconjugation
Cell surface
Chemical compounds
Chemical reactions
Cholesterol
Click reaction
Conjugation
Lipids
Lipoprotein
Lipoproteins
Proteins
Tetrahedrons
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.01.041