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Defluorination of 4-fluorophenol by cytochrome P450BM3-F87G: activation by long chain fatty aldehydes
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“Furthermore, P450BM3-F87G, a mutant form of P450BM3 from Bacillus megaterium, catalyzed the oxidative defluorination of 4-fluorophenol to benzoquinone that was further reduced to hydroquinone through the NADPH P450-reductase (118) (Fig. 4).”
From Toward the development of a molecular toolkit for the microbial remediation of per-and polyfluoroalkyl substances (2024) · cites this paper as [118]
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- Harvey PJ, Campanella BF, Castro PML, Harms H, Lichtfouse E, Schäffner AR, Smrcek S, Werck-Reichhart D (2002) Phytoremediation of polyaromatic hydrocarbons, anilines and phenols. Environ Sci Pollut Res 9:29–47 · DOI
- Key BD, Howell RD, Criddle CS (1997) Fluorinated organics in the biosphere. Environ Sci Technol 31:2445–2454 · DOI · Paper page
- Lau SS, Hill BA, Highet RJ, Monks TJ (1988) Sequential oxidation and glutathione addition to 1,4-benzoquinone: correlation of toxicity with increased glutathione substitution. Mol Pharmacol 34:829–836 · DOI
- Meharg AA, Wright J, Osborn D (2000) Chlorobenzenes in rivers draining industrial catchments. Sci Total Environ 251:243–253 · DOI
- Murphy CD (2007) Fluorophenol oxidation by a fungal chloroperoxidase. Biotechnol Lett 29:45–49 · DOI
- Ohe T, Mashino T, Hirobe M (1997) Substituent elimination form p-substituted phenols by cytochrome P450 ipso substitution by the activated oxygen atom of the activated species. Drug Metab Dispos 25:116–122
- Osborne RL, Raner GM, Hager LP, Dawson JH (2006) C. fumago chloroperoxidase is also a dehaloperoxidase: oxidative dehalogenation of halophenols. J Amer Chem Soc 128:1036–1037 · DOI
- Osborne RL, Coggins MK, Raner GM, Walla M, Dawson JH (2009) The mechanism of oxidative halophenol dehalogenation by Amphitrite ornata dehaloperoxidase is initiated by H2O2 binding and involves two consecutive one-electron steps: role of ferryl intermediates. Biochemistry 48:4231–4238 · DOI
- Osman AM, Boeren S, Veeger C, Rietjens IMCM (1997) MP8-Dependent oxidative dehalogenation: evidence for the direct formation of 1,4-benzoquinone from 4-fluorophenol by a peroxidase-type of reaction pathway. Chem Biol Interact 104:147–164 · DOI
- Raner GM, Hatchell AJ, Morton PE, Ballou DP, Coon MJ (2000) Stopped-flow spectrophotometric analysis of intermediates in the peroxo-dependent inactivation of cytochrome p450 by aldehydes. J Inorg Biochem 81:153–160 · DOI
- Raner GM, Hatchell JA, Dixon MU, Joy T, Haddy AE, Johnston ER (2002) Regioselective peroxo-dependent heme alkylation in p450bm3-f87g by aromatic aldehydes: effects of alkylation on catalysis. Biochemistry 41:9601–9610 · DOI
- Rietjens IMCM, Vervoort J (1992) A new hypothesis for the mechanism for the cytochrome P-450 dependent aerobic conversion of hexahalogenated benzenes to pentahalogenated phenols. Chem Res Toxicol 5:10–19 · DOI
- Schwaneberg U, Schmidt-Dannert C, Schmit J, Schmid RD (1999) A continuous spectrophotometric assay for P450BM-3, a fatty acid hydroxylating enzyme, and its mutant F87A. Anal Biochem 269:359–366 · DOI
- Szatkowski L, Thompson MK, Kaminski R, Franzen S, Dybala-Defratyka A (2011) Oxidative dechlorination of halogenated phenols catalyzed by two distinct enzymes: horseradish peroxidase and dehaloperoxidase. Arch Biochem Biophys 508:22–32 · DOI
- Vatsis KP, Coon MJ (2002) Ipso substitution by Cytochrome P450 with conversion of the p-hydroxybenzene derivatives to hydroquinone: evidence for hydroperoxo-iron as the active oxygen species. Arch Biochem Biophys 397:119–129 · DOI
Cited by
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Berhanu, A., Mutanda, I., Taolin, J., Qaria, M. A., Yang, B., & Zhu, D. (2023) · Science of The Total Environment · doi:10.1016/j.scitotenv.2022.160010 · Cited by 294
Wackett, L. P. (2022) · Microbial Biotechnology · doi:10.1111/1751-7915.13928 · Cited by 165
Hu, M., & Scott, C. (2024) · Applied and Environmental Microbiology · doi:10.1128/aem.00157-24 · Cited by 63
Metadata
- Authors
- Harkey, A., Kim, H.-J., Kandagatla, S., & Raner, G. M.
- Venue
- Biotechnology Letters
- Published
- 2012-05-25
- Volume
- 34
- Issue
- 9
- Pages
- 1725-1731
- ISSN
- 0141-5492
- 1573-6776
- Cited by
- 29
- References
- 0
- Language
- en
- Licence
- www.springer.com/tdm (tdm)
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- CoChat. (2026). Citation check: Defluorination of 4-fluorophenol by cytochrome P450BM3-F87G: activation by long chain fatty aldehydes. https://app.cochat.ai/papers/10.1007/s10529-012-0957-9
- The paper
- Harkey, A., Kim, H.-J., Kandagatla, S., & Raner, G. M. (2012). Defluorination of 4-fluorophenol by cytochrome P450BM3-F87G: activation by long chain fatty aldehydes. Biotechnology Letters. https://doi.org/10.1007/s10529-012-0957-9
