Carbon-fluorine bond cleavage mediated by metalloenzymes.

Chemical Society Reviews
Yifan Wang, Aimin Liu

Abstract

Fluorochemicals are a widely distributed class of compounds and have been utilized across a wide range of industries for decades. Given the environmental toxicity and adverse health threats of some fluorochemicals, the development of new methods for their decomposition is significant to public health. However, the carbon-fluorine (C-F) bond is among the most chemically robust bonds; consequently, the degradation of fluorinated hydrocarbons is exceptionally difficult. Here, metalloenzymes that catalyze the cleavage of this chemically challenging bond are reviewed. These enzymes include histidine-ligated heme-dependent dehaloperoxidase and tyrosine hydroxylase, thiolate-ligated heme-dependent cytochrome P450, and four nonheme oxygenases, namely, tetrahydrobiopterin-dependent aromatic amino acid hydroxylase, 2-oxoglutarate-dependent hydroxylase, Rieske dioxygenase, and thiol dioxygenase. While much of the literature regarding the aforementioned enzymes highlights their ability to catalyze C-H bond activation and functionalization, in many cases, the C-F bond cleavage has been shown to occur on fluorinated substrates. A copper-dependent laccase-mediated system representing an unnatural radical defluorination approach is also descri...Continue Reading

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Citations

Mar 19, 2021·Journal of the American Chemical Society·Yifan WangAimin Liu
Oct 23, 2020·Journal of the American Chemical Society·Jiasong LiAimin Liu
Nov 28, 2020·Archives of Biochemistry and Biophysics·Pablo Sobrado
Apr 29, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Sandip MunshiTapan Kanti Paine
Jun 18, 2021·Chemistry : a European Journal·Andreas DorianFlorence J Williams
Aug 25, 2021·The Science of the Total Environment·Sanny VermaMallikarjuna N Nadagouda
Oct 27, 2021·Chemical Communications : Chem Comm·Juan ZhangZhang Feng
Nov 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lei Zhou

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