Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives

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 o...

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Bibliographic Details
Published in:Organic letters 2005-04, Vol.7 (9), p.1699-1702
Main Authors: Visintin, Cristina, Aliev, Abil E, Riddall, Dieter, Baker, David, Okuyama, Masahiro, Hoi, Pui Man, Hiley, Robin, Selwood, David L
Format: Article
Language:English
Subjects:
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
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Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0502578