Fluorinated S-Adenosylmethionine as a Reagent for Enzyme-Catalyzed Fluoromethylation

Peng, Jiaming and Liao, Cangsong and Bauer, Carste and Seebeck, Florian Peter. (2021) Fluorinated S-Adenosylmethionine as a Reagent for Enzyme-Catalyzed Fluoromethylation. Angewandte Chemie International Edition, 60 (52). pp. 27178-27183.

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Official URL: https://edoc.unibas.ch/87387/

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Strategic replacement of protons with fluorine atoms or functional groups with fluorine-containing fragments has proven a powerful strategy to optimize the activity of therapeutic compounds. For this reason, the synthetic chemistry of organofluorides has been the subject of intense development and innovation for many years. By comparison, the literature on fluorine biocatalysis still makes for a slim chapter. Herein we introduce S-adenosylmethionine (SAM) dependent methyltransferases as a new tool for the production of fluorinated compounds. We demonstrate the ability of halide methyltransferases to form fluorinated SAM (S-adenosyl-S-(fluoromethyl)-L-homocysteine) from S-adenosylhomocysteine and fluoromethyliodide. Fluorinated SAM (F-SAM) is too unstable for isolation, but is accepted as a substrate by C-, N- and O-specific methyltransferases for enzyme-catalyzed fluoromethylation of small molecules.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Bionics (Seebeck)
UniBasel Contributors:Seebeck, Florian Peter
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:08 Nov 2022 02:30
Deposited On:15 Feb 2022 15:44

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