Fontimonas thermophila Alkane Monooxygenase (FtAlkB) Is an Alkyl Fluoride Dehalogenase

Lauren Hendricks; Clorice R. Reinhardt; Tierani Green; Lily Kunczynski; August Jaunzarins Roberts; Naomi Miller; Noga Rafalin; Heather J. Kulik; John T. Groves; Rachel N. Austin

doi:10.1021/jacs.5c00386

Fontimonas thermophila Alkane Monooxygenase (FtAlkB) Is an Alkyl Fluoride Dehalogenase

Lauren Hendricks, Clorice R. Reinhardt, Tierani Green, Lily Kunczynski, August Jaunzarins Roberts, Naomi Miller, Noga Rafalin, Heather J. Kulik, John T. Groves, Rachel N. Austin

Research output: Contribution to journal › Article › peer-review

Abstract

Purified alkane monooxygenase (AlkB) from Fontimonas thermophila (FtAlkB) catalyzes the defluorination of 1-fluorooctane, producing octanal, which is partially reduced under the reaction conditions to generate 1-octanol. This reaction occurs preferentially at the monofluorinated methyl group, with only a minor amount of oxidation at the nonfluorinated end of the molecule. The dehalogenation chemistry is specific to 1-fluorooctane, as neither 1-chlorooctane or 1-bromooctane are dehalogenated to an appreciable extent. Furthermore, P. putida cells containing the structurally related AlkB (PpAlkB) along with the full set of genes required for alkane metabolism, utilize 1-fluorooctane as their sole source of carbon with growth rates comparable to those for cells grown with octane.

Original language	English (US)
Pages (from-to)	9085-9090
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	147
Issue number	11
DOIs	https://doi.org/10.1021/jacs.5c00386
State	Published - Mar 19 2025

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Fontimonas thermophila Alkane Monooxygenase (FtAlkB) Is an Alkyl Fluoride Dehalogenase",

abstract = "Purified alkane monooxygenase (AlkB) from Fontimonas thermophila (FtAlkB) catalyzes the defluorination of 1-fluorooctane, producing octanal, which is partially reduced under the reaction conditions to generate 1-octanol. This reaction occurs preferentially at the monofluorinated methyl group, with only a minor amount of oxidation at the nonfluorinated end of the molecule. The dehalogenation chemistry is specific to 1-fluorooctane, as neither 1-chlorooctane or 1-bromooctane are dehalogenated to an appreciable extent. Furthermore, P. putida cells containing the structurally related AlkB (PpAlkB) along with the full set of genes required for alkane metabolism, utilize 1-fluorooctane as their sole source of carbon with growth rates comparable to those for cells grown with octane.",

author = "Lauren Hendricks and Reinhardt, {Clorice R.} and Tierani Green and Lily Kunczynski and Roberts, {August Jaunzarins} and Naomi Miller and Noga Rafalin and Kulik, {Heather J.} and Groves, {John T.} and Austin, {Rachel N.}",

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doi = "10.1021/jacs.5c00386",

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T1 - Fontimonas thermophila Alkane Monooxygenase (FtAlkB) Is an Alkyl Fluoride Dehalogenase

AU - Hendricks, Lauren

AU - Reinhardt, Clorice R.

AU - Green, Tierani

AU - Kunczynski, Lily

AU - Roberts, August Jaunzarins

AU - Miller, Naomi

AU - Rafalin, Noga

AU - Kulik, Heather J.

AU - Groves, John T.

AU - Austin, Rachel N.

PY - 2025/3/19

Y1 - 2025/3/19

N2 - Purified alkane monooxygenase (AlkB) from Fontimonas thermophila (FtAlkB) catalyzes the defluorination of 1-fluorooctane, producing octanal, which is partially reduced under the reaction conditions to generate 1-octanol. This reaction occurs preferentially at the monofluorinated methyl group, with only a minor amount of oxidation at the nonfluorinated end of the molecule. The dehalogenation chemistry is specific to 1-fluorooctane, as neither 1-chlorooctane or 1-bromooctane are dehalogenated to an appreciable extent. Furthermore, P. putida cells containing the structurally related AlkB (PpAlkB) along with the full set of genes required for alkane metabolism, utilize 1-fluorooctane as their sole source of carbon with growth rates comparable to those for cells grown with octane.

AB - Purified alkane monooxygenase (AlkB) from Fontimonas thermophila (FtAlkB) catalyzes the defluorination of 1-fluorooctane, producing octanal, which is partially reduced under the reaction conditions to generate 1-octanol. This reaction occurs preferentially at the monofluorinated methyl group, with only a minor amount of oxidation at the nonfluorinated end of the molecule. The dehalogenation chemistry is specific to 1-fluorooctane, as neither 1-chlorooctane or 1-bromooctane are dehalogenated to an appreciable extent. Furthermore, P. putida cells containing the structurally related AlkB (PpAlkB) along with the full set of genes required for alkane metabolism, utilize 1-fluorooctane as their sole source of carbon with growth rates comparable to those for cells grown with octane.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

Fontimonas thermophila Alkane Monooxygenase (FtAlkB) Is an Alkyl Fluoride Dehalogenase

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