The para-fluoro-thiol ligation in water

The para -fluoro-thiol reaction (PFTR) is performed for the first time in aqueous media. A water-soluble model scaffold based on poly( N , N -dimethylacrylamide) and incorporating pentafluorostyrene units was synthesized by nitroxide-mediated copolymerization. The effect of pH, temperature, and stoi...

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Bibliographic Details
Published in:Polymer chemistry 2017-02, Vol.8 (8), p.1288-1293
Main Authors: Turgut, Hatice, Schmidt, Aaron C., Wadhwani, Parvesh, Welle, Alexander, Müller, Rouven, Delaittre, Guillaume
Format: Article
Language:English
Subjects:
Copolymerization
Coupling
Culture
Media
NMR spectroscopy
Solvents
Stoichiometry
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Summary:The para -fluoro-thiol reaction (PFTR) is performed for the first time in aqueous media. A water-soluble model scaffold based on poly( N , N -dimethylacrylamide) and incorporating pentafluorostyrene units was synthesized by nitroxide-mediated copolymerization. The effect of pH, temperature, and stoichiometry on the solution-phase kinetics of the PFTR for side-chain modification is studied by 19 F and 1 H NMR spectroscopy using mercaptoethanol as a model thiol. While the reaction can occur from pH 11 on, increasing pH greatly accelerates the reaction. Yields >90% are achieved at pH 12 and 40 °C in 24 h, while quantitative coupling is reached at pH 13 and 50 °C in less than 16 h. Grafting of a cysteine-containing peptide on tissue culture plates demonstrated by ToF-SIMS evidences the benefit of performing this reaction in aqueous media for surface functionalization of materials prone to degradation in organic solvents.
ISSN:1759-9954
1759-9962
DOI:10.1039/C6PY02108E