The para-fluoro-thiol ligation in water

Literature Information

Publication Date 2017-01-16
DOI 10.1039/C6PY02108E
Impact Factor 5.582
Authors

Parvesh Wadhwani, Rouven Müller


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Abstract

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 19F and 1H 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.

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