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
| Autor: | Dominique Bonnet, Rania Dagher, Marie-Céline Frantz, Rita Rahmeh, Marcel Hibert, Laure Boudier, Stéphanie Loison, Jacques Haiech, Stéphanie Riché, Bernard Mouillac |
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| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Receptors Vasopressin Biomolecule Organic Chemistry Water General Chemistry Tripeptide Lithium Ligands Spectrum Analysis Raman Combinatorial chemistry Fluorescence Catalysis Förster resonance energy transfer Solid-phase synthesis chemistry 1 3-Dipolar cycloaddition Click chemistry Electrochemistry Organic chemistry Peptides Linker Fluorescent Dyes |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 14(20) |
| ISSN: | 0947-6539 |
| Popis: | 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 CuI-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 V2 receptor (V2R) 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. |
| Databáze: | OpenAIRE |
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