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Archives of Microbiology

, Volume 177, Issue 3, pp 235–243 | Cite as

Anaerobic degradation of n-hexane in a denitrifying bacterium: Further degradation of the initial intermediate (1-methylpentyl)succinate via C-skeleton rearrangement

  • Heinz Wilkes
  • Ralf Rabus
  • Thomas Fischer
  • Antje Armstroff
  • Astrid Behrends
  • Friedrich Widdel
Original Paper

Abstract.

The anaerobic degradation pathway of the saturated hydrocarbon n-hexane in a denitrifying strain (HxN1) was examined by gas chromatography-mass spectrometry of derivatized extracts from cultures grown with unlabeled and deuterated substrate; several authentic standard compounds were included for comparison. The study was focused on possible reaction steps that follow the initial formation of (1-methylpentyl)succinate from n-hexane and fumarate. 4-Methyloctanoic, 4-methyloct-2-enoic, 2-methylhexanoic, 2-methylhex-2-enoic and 3-hydroxy-2-methylhexanoic acids (in addition to a few other methyl-branched acids) were detected in n-hexane-grown but not in n-hexanoate-grown cultures. Labeling indicated preservation of the original carbon chain of n-hexane in these acids. Tracing of the deuterium label of 3-d 1-(1-methylpentyl)succinate in tentative subsequent products indicated a deuterium/carboxyl carbon exchange in the succinate moiety. This suggests that the metabolism of (1-methylpentyl)succinate employs reactions analogous to those in the established conversion of succinyl-CoA via methylmalonyl-CoA to propionyl-CoA. Accordingly, a pathway is proposed in which (1-methylpentyl)succinate is converted to the CoA-thioester, rearranged to (2-methylhexyl)malonyl-CoA and decarboxylated (perhaps by a transcarboxylase) to 4-methyloctanoyl-CoA. The other identified fatty acids match with a further degradation of 4-methyloctanoyl-CoA via rounds of conventional β-oxidation. Such a pathway would also allow regeneration of fumarate (for n-hexane activation) from propionyl-CoA formed as intermediate and hence present a cyclic process.

(1-Methylpentyl)succinate n-Hexane Anaerobic oxidation Denitrification C-skeleton rearrangement Fatty acid oxidation Methyl-branched fatty acids 

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Copyright information

© Springer-Verlag 2001

Authors and Affiliations

  • Heinz Wilkes
    • 1
  • Ralf Rabus
    • 2
  • Thomas Fischer
    • 1
  • Antje Armstroff
    • 1
  • Astrid Behrends
    • 2
  • Friedrich Widdel
    • 2
  1. 1.Institut für Erdöl und Organische Geochemie, Forschungszentrum Jülich GmbH, 52425 Jülich, Germany
  2. 2.Max-Planck-Institut für marine Mikrobiologie, Celsiusstraße 1, 28359 Bremen, Germany

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