Membrane receptor probes: solid-phase synthesis of biotin-Asp-PEG-arvanil derivatives.
[structure: see text] A modular, flexible solid-phase synthetic route for the preparation of biotinylated cross-linking probes of membrane receptors is described. The route utilizes an orthogonal protection strategy employing a Pd[0] cleavable allyl linker attached to the probe via an aspartate residue. The versatility of the method is illustrated through the synthesis of a number of arvanil-derived cannabinoid receptor ligands displaying either a photoaffinity or a chemical cross-linking group.
Visintin
Cristina
C
The Wolfson Institute for Biomedical Research, Institute of Neurology, and Department of Chemistry, University College London, Gower Street, London WC1E 6BT, UK.
Aliev
Abil E
AE
Riddall
Dieter
D
Baker
David
D
Okuyama
Masahiro
M
Hoi
Pui Man
PM
Hiley
Robin
R
Selwood
David L
DL
D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001710:Biotin / Q000138:chemical synthesis*; D019921:Biotinylation; D002211:Capsaicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003432:Cross-Linking Reagents / Q000138:chemical synthesis; D015335:Molecular Probes / Q000138:chemical synthesis*; D015394:Molecular Structure; D019920:Photoaffinity Labels / Q000138:chemical synthesis; D043882:Receptors, Cannabinoid / Q000378:metabolism
D003432:Cross-Linking Reagents; D015335:Molecular Probes; D019920:Photoaffinity Labels; D043882:Receptors, Cannabinoid; C121153:arvanil; D001224:Aspartic Acid; D001710:Biotin; D002211:Capsaicin