Anaerobic Formation of n-Hept-l-ene from n-Heptane by Resting Cells of Pseudomonas aeruginosa

Chouteau, J.; Azoulay, E.; Senez, Jacques C.

doi:10.1038/194576a0

Cited by 52 publications

(16 citation statements)

References 2 publications

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“…In contrast, strain AK-01 forms C-even fatty acids when grown on C-even alkanes and vice versa (38). Additional evidence reported by Aeckersberg et al (1,3) indicated that 1-alkene was unlikely to be an intermediate, as suggested by earlier literature (8,29).…”

supporting

confidence: 57%

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Phelps

Young

2003

Appl Environ Microbiol

162

106

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Strain Hxd3, an alkane-degrading sulfate reducer previously isolated and described by Aeckersberg et al. (F. Aeckersberg, F. Bak, and F. Widdel, Arch. Microbiol. 156:5-14, 1991), was studied for its alkane degradation mechanism by using deuterium and 13 C-labeled compounds. Deuterated fatty acids with even numbers of C atoms (C-even) and 13 C-labeled fatty acids with odd numbers of C atoms (C-odd) were recovered from cultures of Hxd3 grown on perdeuterated pentadecane and [1,2-13 C 2 ]hexadecane, respectively, underscoring evidence that C-odd alkanes are transformed to C-even fatty acids and vice versa. When Hxd3 was grown on unlabeled hexadecane in the presence of [ 13 C]bicarbonate, the resulting 15:0 fatty acid, which was one carbon shorter than the alkane, incorporated a 13 C label to form its carboxyl group. The same results were observed when tetradecane, pentadecane, and perdeuterated pentadecane were used as the substrates. These observations indicate that the initial attack of alkanes includes both carboxylation with inorganic bicarbonate and the removal of two carbon atoms from the alkane chain terminus, resulting in a fatty acid one carbon shorter than the original alkane. The removal of two terminal carbon atoms is further evidenced by the observation that the [1,2-13 C 2 ]hexadecane-derived fatty acids contained either two 13 C labels located exclusively at their acyl chain termini or none at all. Furthermore, when perdeuterated pentadecane was used as the substrate, the 14:0 and 16:0 fatty acids formed both carried the same numbers of deuterium labels, while the latter was not deuterated at its carboxyl end. These observations provide further evidence that the 14:0 fatty acid was initially formed from perdeuterated pentadecane, while the 16:0 fatty acid was produced after chain elongation of the former fatty acid with nondeuterated carbon atoms. We propose that strain Hxd3 anaerobically transforms an alkane to a fatty acid through a mechanism which includes subterminal carboxylation at the C-3 position of the alkane and elimination of the two adjacent terminal carbon atoms.

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supporting

confidence: 57%

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Phelps

Young

2003

Appl Environ Microbiol

162

106

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“…The degradation of 1-hexadecene by methanogenic enrichment cultures was supposed to occur by initial oxidation to 1-hexadecanol and subsequent ␤-oxidation of hexadecanoic acid (28), but no intermediate metabolite other than acetate could be detected. On the other hand, in some early studies of alkane-degrading microorgan-isms, an oxygen-independent initial metabolism of alkanes via dehydrogenation to 1-alkenes and oxidation to primary alcohols was suggested (6,23,35). In recent investigations, however, alkane dehydrogenation to 1-alkenes was viewed critically (1,2,30), and two alternative pathways for the initial oxidation of alkanes in denitrifying or sulfate-reducing bacteria were subsequently described: the addition of fumarate at C-2 (5,8,24,38) and carboxylation at C-3 (5,29).…”

mentioning

confidence: 99%

Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803 ^T

Grossi

Cravo‐Laureau

Méou³

et al. 2007

Appl Environ Microbiol

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The alkane-and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T , known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total cellular fatty acids of this strain were predominantly C-(even number) (C-even) when it was grown on C-even 1-alkenes and predominantly C-(odd number) (C-odd) when it was grown on C-odd 1-alkenes. Detailed analyses of those fatty acids by gas chromatography-mass spectrometry after 6-to 10-week incubations allowed the identification of saturated 2-and 4-ethyl-, 2-and 4-methyl-, and monounsat-

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“…They are known to be more easily degradable than alkanes. In some earlier reports alkenes were considered to be intermediates in Offprint requests to: M. Gilewicz the oxidation of alkanes (Chouteau et al 1962;Azoulay et al 1963;Wagner et al 1967;Iizuka et alo 1969;Iida and Iizuka 1970).…”

Section: Introductionmentioning

confidence: 99%

Anaerobic oxidation of 1-n-heptadecene by a marine denitrifying bacterium

Gilewicz

Monpert

Acquaviva

et al. 1991

Appl Microbiol Biotechnol

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A denitrifying bacterium showing typical characteristics of Pseudomonas sp. (All) capable of growth on 1-heptadecene as the sole source of carbon and energy has been isolated from a hydrocarbon-polluted marine sediment by using classical enrichment techniques. The generation time for anaerobic growth on 1-heptadecene was 24 h, and the percentage of hydrocarbon degradation under anaerobic conditions ranged from 19 to 23%. The emulsifying capacity was observed and suggested that All cultivated anaerobically on heptadecene produced surface-active agents.

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Anaerobic Formation of n-Hept-l-ene from n-Heptane by Resting Cells of Pseudomonas aeruginosa

Cited by 52 publications

References 2 publications

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803 ^T

Anaerobic oxidation of 1-n-heptadecene by a marine denitrifying bacterium

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Anaerobic Formation of n-Hept-l-ene from n-Heptane by Resting Cells of Pseudomonas aeruginosa

Cited by 52 publications

References 2 publications

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803 T

Anaerobic oxidation of 1-n-heptadecene by a marine denitrifying bacterium

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Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803 ^T