On-resin cyclization of peptide ligands of the Vascular Endothelial Growth Factor Receptor 1 by copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition

Victor Goncalves; Benoit Gautier; Anne Regazzetti; Pascale Coric; Serge Bouaziz; Christiane Garbay; Michel Vidal; Nicolas Inguimbert

doi:10.1016/j.bmcl.2007.07.087

On-resin cyclization of peptide ligands of the Vascular Endothelial Growth Factor Receptor 1 by copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition

Bioorg Med Chem Lett. 2007 Oct 15;17(20):5590-4. doi: 10.1016/j.bmcl.2007.07.087. Epub 2007 Aug 22.

Authors

Victor Goncalves¹, Benoit Gautier, Anne Regazzetti, Pascale Coric, Serge Bouaziz, Christiane Garbay, Michel Vidal, Nicolas Inguimbert

Affiliation

¹ Université Paris Descartes, UFR biomédicale, Laboratoire de Pharmacochimie Moléculaire et Cellulaire, 45 rue des saints Pères, F-75006 Paris, France.

PMID: 17826090
DOI: 10.1016/j.bmcl.2007.07.087

Abstract

Cyclic peptides were obtained, on-resin, by the copper (I) catalysed 1,3-dipolar cycloaddition of azides and alkynes. The reaction led exclusively to the formation of the expected cyclomonomeric products which acted as ligands of the Vascular Endothelial Growth Factor receptor 1.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Amino Acid Sequence
Azides / chemistry*
Catalysis
Chromatography, High Pressure Liquid
Copper / chemistry*
Crystallography, X-Ray
Cyclization
Ligands
Models, Molecular
Molecular Sequence Data
Peptides / chemistry*
Peptides / metabolism*
Protein Binding
Protein Structure, Quaternary
Vascular Endothelial Growth Factor A / chemistry
Vascular Endothelial Growth Factor A / metabolism
Vascular Endothelial Growth Factor Receptor-1 / chemistry*
Vascular Endothelial Growth Factor Receptor-1 / metabolism*

Substances

Alkynes
Azides
Ligands
Peptides
Vascular Endothelial Growth Factor A
Copper
Vascular Endothelial Growth Factor Receptor-1