Membrane receptor probes: solid-phase synthesis of biotin-Asp-PEG-arvanil derivatives

Cristina Visintin; Abil E Aliev; Dieter Riddall; David Baker; Masahiro Okuyama; Pui Man Hoi; Robin Hiley; David L Selwood

doi:10.1021/ol0502578

Membrane receptor probes: solid-phase synthesis of biotin-Asp-PEG-arvanil derivatives

Org Lett. 2005 Apr 28;7(9):1699-702. doi: 10.1021/ol0502578.

Authors

Cristina Visintin¹, Abil E Aliev, Dieter Riddall, David Baker, Masahiro Okuyama, Pui Man Hoi, Robin Hiley, David L Selwood

Affiliation

¹ The Wolfson Institute for Biomedical Research, Institute of Neurology, and Department of Chemistry, University College London, Gower Street, London WC1E 6BT, UK.

PMID: 15844884
DOI: 10.1021/ol0502578

Abstract

[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.

Publication types

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

MeSH terms

Aspartic Acid / analogs & derivatives*
Aspartic Acid / chemical synthesis*
Biotin / chemical synthesis*
Biotinylation
Capsaicin / analogs & derivatives*
Capsaicin / chemical synthesis
Cross-Linking Reagents / chemical synthesis
Molecular Probes / chemical synthesis*
Molecular Structure
Photoaffinity Labels / chemical synthesis
Receptors, Cannabinoid / metabolism

Substances

Cross-Linking Reagents
Molecular Probes
Photoaffinity Labels
Receptors, Cannabinoid
arvanil
Aspartic Acid
Biotin
Capsaicin