Stereochemical Studies of Acyclic Isoprenoid Compounds. III. The Stereochemistry of Naturally Occurring (Marine) 2,6,10,14-Tetramethylpentadecane

Cox, Robert E.; Maxwell, J. R.; Ackman, R. G.; Hooper, S. N.

doi:10.1139/o72-167

Cited by 34 publications

(12 citation statements)

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“…Based on previous reports for M. fortuitum (9) and N. globerula 432 (1), Mycobacterium sp. strain P101 was assumed to oxidize pristane through monoterminal oxidation; i.e., pristanic acid is thioesterified with CoA to form pristanoyl-CoA and then degraded by ␤-oxidation.…”

Section: Discussionmentioning

confidence: 99%

“…(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: 99%

“…Some bacteria are capable of degrading the pristane present in crude oil, which is a mixture of a variety of stereoisomers at C-6 and C-10. Pristane is a common constituent of the lipids of many marine organisms (9), and a typical biogenic pristane, which is obtained from shark liver, has a (6R,10S)-meso configuration (9). In contrast, pristane of fossil origin is a mixture of diastereomers.…”

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confidence: 99%

“…M. fortuitum is known to use several configurations of pristane and preferentially oxidizes the biogenic (6R,10S) isomer. However, previous reports (4,8,9) have not been concerned with the stereospecificity of ␤-oxidation, and both enzymological information and genetic information on bacterial pristanic acid oxidation are very limited. Recently, Bhaumik et al found three genes, mcr, far, and Rv3727, which encode proteins homologous to mammalian ␣-methylacyl-CoA racemase in the Mycobacterium tuberculosis genome (5).…”

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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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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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“…The other possible sterioisomeric molecules are formed by racemization. This has been demonstrated in the lower boiling range (Cox et al, 1972;Patience et al, 1978) of a hydrocarbon mixture with the diasteriomeric isoprenoid alkanes: 2, 6, 10 -trimethyltetradecane (2, 6, 10 -C17), norpristane (norpri), pristane (pri) and phytane (phy) -and for the upper boiling range, for the diastereoisomeric steranes: the cholestanes and hopanes Dastillung & Albrecht, 1976). Using as an example a glass-capillary gas chromatogram of the aliphatic and alicyclic fraction of Ekofisk oil may explain this phenomenon.…”

Section: Problems In Chemical Analysismentioning

confidence: 70%

Oil, oil dispersants and related substances in the marine environment

Gunkel

Gassmann

1980

Helgolander Meeresunters

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Enantiomeric composition and prevalence of some bicyclic monoterpenoids in amber

et al. 1996

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Among the more prevalent chiral monoterpenoid compounds in conifers are α‐pinene, β‐pinene, and smaller amounts of camphene and limonene. The most prevalent chiral monoterpenoid compounds in fossilized resin (referred to as amber in this paper) appear to be borneol, isoborneol, and camphene. Most of these compounds have easily measured enantiomeric excesses. The borneol and isoborneol in some amber samples have pronounced enantiomeric excesses despite the fact that they are tens of millions of years old. The enantiomeric ratios of the monoterpenoids in different ambers vary tremendously and often are distinct. However, in any single amber sample, the stereochemistry (absolute configuration) of the excess monoterpenoid enantiomers appears to be identical. The camphene in amber may be a secondary reaction product formed over time, possibly from the dehydration of borneol. Although a compound's original stereochemistry can be preserved, it also may diminish with the number and type of chemical transformations over geological time. The monoterpene enantiomeric ratios in modern conifer resins vary tremendously. Future stereochemical studies are outlined that could provide the data necessary for more exact geochemical interpretations and possibly for obtaining pertinent paleobiological information. © 1996 Wiley‐Liss, Inc.

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Stereochemical Studies of Acyclic Isoprenoid Compounds. III. The Stereochemistry of Naturally Occurring (Marine) 2,6,10,14-Tetramethylpentadecane

Cited by 34 publications

References 4 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

Oil, oil dispersants and related substances in the marine environment

Enantiomeric composition and prevalence of some bicyclic monoterpenoids in amber

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