Microbial Oxidation of the Isoprenoid Alkane Pristane

Nakajima, Kenji; Sato, Akio; Misono, Terunobu; Iida, Takeo; Nagayasu, Kozo

doi:10.1080/00021369.1974.10861446

Agricultural and Biological Chemistry

1974

DOI: 10.1080/00021369.1974.10861446

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Microbial Oxidation of the Isoprenoid Alkane Pristane

Kenji Nakajima

Akio Sato

Terunobu Misono

et al.

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Cited by 11 publications

(10 citation statements)

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“…(22), Rhodococcus sp. (23), Nocardia globerula 432 (1), and Mycobacterium fortuitum (8). The combination of the findings suggests that pristane is oxidized to pristanic acid and then esterified with coenzyme A (CoA) to form pristanoyl-CoA, which is ␤-oxidized.…”

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confidence: 93%

Role of α-Methylacyl Coenzyme A Racemase in the Degradation of Methyl-Branched Alkanes by Mycobacterium sp. Strain P101

et al. 2004

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A new isolate, Mycobacterium sp. strain P101, is capable of growth on methyl-branched alkanes (pristane, phytane, and squalane). Among ca. 10,000 Tn5-derived mutants, we characterized 2 mutants defective in growth on pristane or n-hexadecane. A single copy of Tn5 was found to be inserted into the coding region of mcr (␣-methylacyl coenzyme A [␣-methylacyl-CoA] racemase gene) in mutant P1 and into the coding region of mls (malate synthase gene) in mutant H1. Mutant P1 could not grow on methyl-branched alkanes. The recombinant Mcr produced in Escherichia coli was confirmed to catalyze racemization of (R)-2-methylpentadecanoyl-CoA, with a specific activity of 0.21 mol ⅐ min ؊1 ⅐ mg of protein ؊1 . Real-time quantitative reverse transcriptase PCR analyses indicated that mcr gene expression was enhanced by the methyl-branched alkanes pristane and squalane. Mutant P1 used (S)-2-methylbutyric acid for growth but did not use the racemic compound, and growth on n-hexadecane was not inhibited by pristane. These results suggested that the oxidation of the methyl-branched alkanoic acid is inhibited by the (R) isomer, although the (R) isomer was not toxic during growth on n-hexadecane. Based on these results, Mcr is suggested to play a critical role in ␤-oxidation of methyl-branched alkanes in Mycobacterium. On the other hand, mutant H1 could not grow on n-hexadecane, but it partially retained the ability to grow on pristane. The reduced growth of mutant H1 on pristane suggests that propionyl-CoA is available for cell propagation through the 2-methyl citric acid cycle, since propionyl-CoA is produced through ␤-oxidation of pristane.

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Role of α-Methylacyl Coenzyme A Racemase in the Degradation of Methyl-Branched Alkanes by Mycobacterium sp. Strain P101

et al. 2004

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“…Thus, pristane (2,6,10,14-tetramethylpentadecane) was often used as an internal standard to determine biodegradation and weathering of other oil fractions (Alvarez et al, 2001). More recently, however, species of several genera have been shown to biodegrade pristane (McKenna & Kallio, 1971;Pirnik et al, 1974;Nakajima & Sato, 1983;Lal & Khanna, 1996;Alvarez et al, 2001). The longer and more heavily substituted molecule squalane (2,6,10,15,19,23-hexamethyltetracosane) has, to date, only been shown to be catabolized by two Mycobacterium species (Berekaa & Steinbüchel, 2000).…”

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Alkanindiges illinoisensis gen. nov., sp. nov., an obligately hydrocarbonoclastic, aerobic squalane-degrading bacterium isolated from oilfield soils

Bogan

Sullivan

Kayser

et al. 2003

International Journal of Systematic and Evolutionary Microbiology

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Alkanindiges illinoisensis gen. nov., sp. nov., an obligately hydrocarbonoclastic, aerobic squalanedegrading bacterium isolated from oilfield soils An alkane-degrading bacterium, designated GTI MVAB Hex1 T , was isolated from chronically crude oil-contaminated soil from an oilfield in southern Illinois. The isolate grew very weakly or not at all in minimal or rich media without hydrocarbons. Straight-chain aliphatic hydrocarbons, such as hexadecane and heptadecane, greatly stimulated growth; shorter-chain (¡C 15 ) hydrocarbons did not (with decane as the sole exception). Growth was also greatly enhanced by the branched aliphatic hydrocarbons pristane and squalane. The latter of these was most intriguing, as catabolism of squalane has hitherto been reported only for Mycobacterium species. Although unable to utilize mono-or polycyclic aromatic hydrocarbons as sole carbon sources, the isolate did show slight fluorene-mineralizing capability in Luria-Bertani medium, which was partially repressed by hexadecane. In contrast, hexadecane supplementation greatly increased mineralization of 14 C-dodecane, which was not a growth substrate. Further testing emphasized the isolate's extremely narrow substrate range, as only Tween 40 and Tween 80 supported significant growth. Microscopic examination (by scanning and transmission electron microscopy) revealed a slightly polymorphic coccoidal to bacillar morphology, with hydrocarbon-grown cells tending to be more elongated. When grown with hexadecane, GTI MVAB Hex1 T accumulated a large number of electron-transparent intracytoplasmic inclusion bodies. These were also prevalent during growth in the presence of squalane. Smaller inclusion bodies were observed occasionally with pristane supplementation; they were, however, absent during growth on crude oil. On the basis of 16S rRNA gene sequence data and range of growth substrates, classification of this isolate as the type strain of Alkanindiges illinoisensis gen. nov., sp. nov. is proposed, which is most closely related (approx. 94 % sequence similarity) to Acinetobacter junii.Bacterial biodegradation of crude oil first gained widespread attention as a potential remediation approach in the 1970s (Atlas & Bartha, 1972;Soli & Bens, 1972). Many bacteria degrade aliphatic constituents of crude oils, including straight-chain aliphatic hydrocarbons up to C 44 (Sakai et al., 1994;Radwan et al., 1996). Branched-chain alkanes, particularly those with anteiso-terminal branching [substitution on carbon atoms that are immediately adjacent to the terminal carbon atom(s)], are much less susceptible to b-oxidation (Schaeffer et al., 1979), and thus more recalcitrant, than their unbranched counterparts. Thus, pristane (2,6,10,14-tetramethylpentadecane) was often used as an internal standard to determine biodegradation and weathering of other oil fractions (Alvarez et al., 2001). More recently, however, species of several genera have been shown to biodegrade pristane (McKenna & Kallio, 1971;Pirnik et al., 1974;Nakajima & Sato, 1983;Lal & Khanna, ...

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“…The minimal medium contained 4.0 g of (NH 4 hHP0 4 , 2.S g of Na z HP0 4 sp. strain 11 B, which showed better growth on 2,S-DMH than the others, was selected and used primarily for further work.…”

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“…Five hundred-ml shake 4 ' 7H 2 0, and I liter of deionized water, pH 8.0, and then resuspended in the reaction medium to make 5 to 10 mg-dry cells/ml. The reactions were started by adding 50,u1 of the substrate to 5 ml of the cell suspension and reaction mixtures were incubated at 30°C for 24 h in a stoppered 24 mm</> test tube with reciprocal shaking.…”

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confidence: 99%

Asymmetric Oxidation of Isopropyl Moieties of Aliphatic and Aromatic Hydrocarbons byRhodococcussp. 11B

Matsui

Furuhashi

1995

Bioscience, Biotechnology, and Biochemistry

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Microbial Oxidation of the Isoprenoid Alkane Pristane

Cited by 11 publications

References 2 publications

Role of α-Methylacyl Coenzyme A Racemase in the Degradation of Methyl-Branched Alkanes by Mycobacterium sp. Strain P101

Role of α-Methylacyl Coenzyme A Racemase in the Degradation of Methyl-Branched Alkanes by Mycobacterium sp. Strain P101

Alkanindiges illinoisensis gen. nov., sp. nov., an obligately hydrocarbonoclastic, aerobic squalane-degrading bacterium isolated from oilfield soils

Asymmetric Oxidation of Isopropyl Moieties of Aliphatic and Aromatic Hydrocarbons byRhodococcussp. 11B

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