Alkanes biochemical

Bowman, R. N. 1983. Intraspecffic variabihty of leaf cuticle alkanes in Sedum lanceolatum along an elevahonal gradient. Biochem. Syst. Ecol. 11 195-198. 

Kawamoto S, C Nozaki, A Tanaka, S Fukui (1978) Fatty acid P-oxidation system in microbodies of -alkane-grown Candida tropicalis. Eur J Biochem 83 609-613. 

Colby J, DI Stirling, H Dalton (1977) The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate -alkanes, -alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds. Biochem J 165 395-401. 

Janssen DB, J Gerritse, J Brackman, C Kalk, D Jager, B Witholt (1988) Purification and characterization of a bacterial dehalogenase with activity towards halogenated alkanes, alcohols and ethers. Eur J Biochem 171 67-72. 

Reviews on the microbial metabolism of hydrocarbons with biochemical aspects are available, and inclnde those of Britton (1984) on alkanes, and of Morgan and Watkinson (1994) that also includes cycloalkanes and some aromatic compounds. Virtually all the issues that are discussed in these recur in the examples that are used as illustration. Some broad generalizations are summarized ... 

Nastainczyk W, Ahr HJ, Ullrich V. 1982b. The reductive metabolism of halogenated alkanes by liver microsomal cytochrome P450. Biochem Pharmacol 31 391-396. 

Cheeseman KH, Albano EF, Tomasi A, et al. 1985. Biochemical studies on the metabolic activation of halogenated alkanes. Environ Health Perspect 64 85-101. 

Leadbetter, E.R. and Foster. J.W. Oxidation products formed from gaseous alkanes by the bacterium Pseudomonas methanica. Arch. Biochem. Biophys., 82 491-492, 1959. 

Durk H, Klessen C, Frank H. 1987. Tetrachloromethane metabolism in vivo under normoxia and hypoxia biochemical and histopathological effects relative to alkane exhalation. Arch Toxicol 60 115-121. 

Colby, J., D. I. Stirling, and H. Dalton, The soluble methane monooxygenase from Methylococcus copsulatus bath - Its ability to oxygenate n-alkanes, ethers and alicyclic, aromatic, and heterocyclic compounds , Biochem. J., 165, 395-402 (1977). 

The first step in oxidation of alkanes is usually an 02-requiring hydroxylation (Chapter 18) to a primary alcohol. Further oxidation of the alcohol to an acyl-CoA derivative, presumably via the aldehyde (Eq. 17-2), is a frequently encountered biochemical oxidation sequence. 

Shanklin J., Whittle E. and Fox B. G. (1994) Eight histidine residues are catalytically essential in a membrane associated iron enzyme, stearoyl-CoA desaturase and are conserved in alkane hydroxylase and xylene monooxygenase. Biochem. 33, 12787-12794. 

Dennis M. W. and Kolattukudy P. E. (1991) Alkane biosynthesis by decarbonylation of aldehyde catalyzed by a microsomal preparation from Botryococcus brauni. Arch. Biochem. Biophys. 287, 268-275. 

Chu A. J. and Blomquist G. J. (1980) Biosynthesis of hydrocarbons in insects succinate is a precursor of the methyl branched alkanes. Arch. Biochem. Biophys. 201, 304-312. 

Blomquist, G.J. and Jackson, L.L. (1973b). Hydroxylation of n-alkanes to secondary alcohols and their esterification in the grasshopper Melanoplus sanguinipes. Biochem. Biophys. Res. Comm., 53, 703-708. 

Bognar, A.L., Paliyath, G., Rogers, L. and Kolattukudy, P.E. (1984). Biosynthesis of alkanes by particulate and solubilized enzyme preparations from pea leaves (Pisum sativum). Arch. Biochem. Biophys., 235, 8-17. 

Yoder, J.A., Denlinger, D.L., Dennis, M. W. and Kolattukudy, RE. (1992). Enhancement of diapausing flesh fly puparia with additional hydrocarbons and evidence for alkane biosynthesis by a decarbonylation mechanism. Insect Biochem. Mol. Biol., 22, 237-243. 

Lehmler, H.-J., Bergosh, R.G., Meier, M.S. and Carlson, R.M.K. (2002). A novel synthesis of branched high-molecular-weight (C40+) long-chain alkanes. Biosci. Biotech. Biochem., 66, 523-531. 

Blomquist, G. J. (1989). Novel very long-chain methyl-branched alcohols and their esters, and methyl-branched alkanes in pupae of the cabbage looper, Trichoplusia ni (Flubner). Insect Biochem., 19, 197-208. 

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