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Anaerobic Degradation of Hydrocarbons: Mechanisms of Hydrocarbon Activation in the Absence of Oxygen

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Anaerobic Utilization of Hydrocarbons, Oils, and Lipids

Part of the book series: Handbook of Hydrocarbon and Lipid Microbiology ((HHLM))

Abstract

Hydrocarbons are highly abundant in nature and are formed either via geochemical or biological processes. Their high C–H bond dissociation energies are responsible for low chemical reactivities. Due to the toxicity of many hydrocarbons, their biological degradation is of environmental concern. In the presence of oxygen, the C–H bond is activated by oxygenases involving enzyme-bound reactive oxygen species in exergonic reactions. In contrast, anaerobic hydrocarbon-degrading bacteria use a number of alternative enzymatic reactions for the mechanistically sophisticated C–H bond activation. Some of these reactions are only known from anaerobic hydrocarbon degradation pathways, and some follow unprecedented biochemical mechanisms. The known oxygen-independent activation reactions of hydrocarbons comprise (1) hydroxylation with water by enzymes containing molybdenum or flavin cofactors, (2) addition to fumarate by glycyl-radical enzymes, (3) carboxylation, (4) water addition at multiple bonds, and (5) reverse methanogenesis. Our current knowledge of these enzymes varies greatly. Whereas an ethylbenzene hydroxylating molybdenum enzyme, a glycyl-radical enzyme adding alkyl groups to fumarate, and different types of enzymes adding water to C=C double and triple bonds have structurally and functionally been characterized, less is known about enzyme(s) involved in naphthalene carboxylation and methane degradation via reverse methanogenesis. The initial mode of benzene activation is still at issue (carboxylation vs. hydroxylation).

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Authors and Affiliations

  1. Microbiology, Faculty of Biology, Albert-Ludwigs-Universität Freiburg, Freiburg, Germany

    Matthias Boll & Sebastian Estelmann

  2. Institute of Biology II, Microbiology, Albert-Ludwigs-Universität Freiburg, Freiburg, Germany

    Matthias Boll

  3. Faculty of Biology, Institute of Biologie II, Universität Freiburg, Freiburg, Germany

    Sebastian Estelmann

  4. Fachbereich Biologie, Universität Marburg, Marburg, Germany

    Johann Heider

  5. Laboratory of Microbial Biochemistry, and LOEWE-Center for Synthetic Microbiology, Philipps-University of Marburg, Marburg, Germany

    Johann Heider

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  1. Matthias Boll
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  2. Sebastian Estelmann
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  3. Johann Heider
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Correspondence to Matthias Boll .

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  1. Microbiology, Faculty of Biology, Albert-Ludwigs-Universität Freiburg, Freiburg, Germany

    Matthias Boll

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Boll, M., Estelmann, S., Heider, J. (2020). Anaerobic Degradation of Hydrocarbons: Mechanisms of Hydrocarbon Activation in the Absence of Oxygen. In: Boll, M. (eds) Anaerobic Utilization of Hydrocarbons, Oils, and Lipids. Handbook of Hydrocarbon and Lipid Microbiology . Springer, Cham. https://doi.org/10.1007/978-3-319-50391-2_2

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