Solid-Phase Organic Tagging Resins for Labeling Biomolecules by 1,3-Dipolar Cycloaddition: Application to the Synthesis of a Fluorescent Non-Peptidic Vasopressin Receptor Ligand
✍ Scribed by Dominique Bonnet; Stéphanie Riché; Stéphanie Loison; Rania Dagher; Marie-Céline Frantz; Laure Boudier; Rita Rahmeh; Bernard Mouillac; Jacques Haiech; Marcel Hibert
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 422 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
Two novel solid‐phase organic tagging (SPOrT) resins were synthesized to facilitate the labeling of peptides and small organic compounds with a fluorescent probe. Both resins were obtained from the commercially available backbone amide linker (BAL) resin. Following the solid‐phase synthesis of model compounds, a tripeptide and benzazepine, the fluorescent probe derived from Lissamine Rhodamine B was incorporated through Cu^I^‐catalyzed 1,3‐dipolar cycloaddition. Final cleavage in acidic media enabled access to both types of molecules in good yield with high purity. The SPOrT resin was successfully applied to the preparation of the first non‐peptidic fluorescent compound with a nanomolar affinity for the human vasopressin V~2~ receptor (V~2~R) subtype. This molecule will find application in binding assays that use polarization or fluorescence resonance energy‐transfer (FRET) techniques. The SPOrT resins are also well suited for other tags and the parallel synthesis of a fluorescently tagged library for protein screening.