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Journal of Bacteriology, March 2001, p. 1707-1715, Vol. 183, No. 5
0021-9193/01/$04.00+0   DOI: 10.1128/JB.183.5.1707-1715.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

Anaerobic Initial Reaction of n-Alkanes in a Denitrifying Bacterium: Evidence for (1-Methylpentyl)succinate as Initial Product and for Involvement of an Organic Radical in n-Hexane Metabolism†

Ralf Rabus,1,* Heinz Wilkes,2 Astrid Behrends,1 Antje Armstroff,2 Thomas Fischer,2 Antonio J. Pierik,3 and Friedrich Widdel1

Max-Planck-Institut für Marine Mikrobiologie, D-28359 Bremen,1 Institut für Erdöl und Organische Geochemie, Forschungszentrum Jülich GmbH, D-52425 Jülich,2 and Laboratorium für Mikrobiologie, Philipps Universität, D-35032 Marburg,3 Germany

Received 7 August 2000/Accepted 6 December 2000

A novel type of denitrifying bacterium (strain HxN1) with the capacity to oxidize n-alkanes anaerobically with nitrate as the electron acceptor to CO2 formed (1-methylpentyl)succinate (MPS) during growth on n-hexane as the only organic substrate under strict exclusion of air. Identification of MPS by gas chromatography-mass spectrometry was based on comparison with a synthetic standard. MPS was not formed during anaerobic growth on n-hexanoate. Anaerobic growth with [1-13C]n-hexane or d14-n-hexane led to a 1-methylpentyl side chain in MPS with one 13C atom or 13 deuterium atoms, respectively. This indicates that the 1-methylpentyl side chain originates directly from n-hexane. Electron paramagnetic resonance spectroscopy revealed the presence of an organic radical in n-hexane-grown cells but not in n-hexanoate-grown cells. Results point at a mechanistic similarity between the anaerobic initial reaction of n-hexane and that of toluene, even though n-hexane is much less reactive; the described initial reaction of toluene in anaerobic bacteria is an addition to fumarate via a radical mechanism yielding benzylsuccinate. We conclude that n-hexane is activated at its second carbon atom by a radical reaction and presumably added to fumarate as a cosubstrate, yielding MPS as the first stable product. When 2,3-d2-fumarate was added to cultures growing on unlabeled n-hexane, 3-d1-MPS rather than 2,3-d2-MPS was detected, indicating loss of one deuterium atom by an as yet unknown mechanism.

* Corresponding author. Mailing address: Max-Planck-Institut für Marine Mikrobiologie, Celsiusstrasse 1, D-28359 Bremen, Germany. Phone: 49-421-2028-736. Fax: 49-421-2028-790. E-mail: rrabus{at}mpi-bremen.de.

dagger This article is dedicated to Wolfgang Buckel on the occasion of his 60th birthday.

Journal of Bacteriology, March 2001, p. 1707-1715, Vol. 183, No. 5
0021-9193/01/$04.00+0   DOI: 10.1128/JB.183.5.1707-1715.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.


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