The para-fluoro-thiol ligation in water

文献信息

发布日期 2017-01-16

DOI 10.1039/C6PY02108E

影响因子 5.582

作者

Parvesh Wadhwani, Rouven Müller

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摘要

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.

期刊推荐

New Journal of Chemistry

Journal of Peptide Science

Nature Medicine

Russian Journal of Coordination Chemistry

Russian Journal of Bioorganic Chemistry

Russian Journal of Organic Chemistry

Current Opinion in Solid State & Materials Science

Organic Process Research & Development

Russian Chemical Bulletin

Chemical Communications

来源期刊

Polymer Chemistry

CiteScore: 8.6

自引率: 7.3%

年发文量: 457

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.

The para-fluoro-thiol ligation in water

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来源期刊

Polymer Chemistry

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