Enzymatic Fluoromethylation Enabled by the S-Adenosylmethionine Analog Te-Adenosyl- L-(fluoromethyl)homotellurocysteine

Syam Sundar Neti, Bo Wang, David F. Iwig, Elizabeth L. Onderko, Squire J. Booker

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Fluoromethyl, difluoromethyl, and trifluoromethyl groups are present in numerous pharmaceuticals and agrochemicals, where they play critical roles in the efficacy and metabolic stability of these molecules. Strategies for late-stage incorporation of fluorine-containing atoms in molecules have become an important area of organic and medicinal chemistry as well as synthetic biology. Herein, we describe the synthesis and use of Te-adenosyl-L-(fluoromethyl)homotellurocysteine (FMeTeSAM), a novel and biologically relevant fluoromethylating agent. FMeTeSAM is structurally and chemically related to the universal cellular methyl donor S-adenosyl-L-methionine (SAM) and supports the robust transfer of fluoromethyl groups to oxygen, nitrogen, sulfur, and some carbon nucleophiles. FMeTeSAM is also used to fluoromethylate precursors to oxaline and daunorubicin, two complex natural products that exhibit antitumor properties.

Original languageEnglish (US)
Pages (from-to)905-914
Number of pages10
JournalACS Central Science
Volume9
Issue number5
DOIs
StatePublished - May 24 2023

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • General Chemical Engineering

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