Summary
A gaseous hydrocarbon-assimilating microorganism, Nocardia corallina, grew on 1-alkenes (C3, C4 and C13 to C18) and produced corresponding 1,2-epoxyalkanes. One of the products, 1,2-epoxytetradecane, had a positive rotation [α] 20D =+8.6°. The concentration of propyleneoxide reached 0.6 g/l after 5 days of cultivation. Accumulation of 1,2-epoxytetradecane continued till the end of cultivation when the pH was not controlled, though production stopped in a 24 h cultivation when the pH was controlled at an optimum pH for growth. Propylene-grown cells produced 1,2-epoxytetradecane from 1-tetradecene and degraded tetradecane. In the presence of chloramphenicol, propylene-grown cells did not degraded tetradecane though 1,2-epoxytetradecane was produced from 1-tetradecene. A spontaneous mutant, which neither grew on propylene nor produced propyleneoxide, was isolated. This strain grew on tetradecane and 1-tetradecene but produced only a trace amount of 1,2-epoxytetradecane from 1-tetradecene.
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References
Abbott BJ, Hou CT (1973) Oxidation of 1-alkenes to 1,2-epoxyaklanes by Pseudomonas oleovorans. Appl Microbiol 26:86–91
Hou CT, Patel R, Laskin AI, Barnabe N (1979) Microbial oxidation of gaseous hydrocarbons. Epoxidation of C2 to C4 n-alkenes by methylotrophic bacteria. Appl Environ Microbiol 38:127–134
Klug MJ, Markovetz AJ (1968) Degradation of hydrocarbons by members of genus Candida. III. Oxidative intermediates from 1-hexadecene and 1-heptadecene by Candida lipolytica. J Bacteriol 96:1115–1123
Linden AC van der (1963) Epoxidation of α-olefins by heptanegrown Pseudomonas cells. Biochim Biophys Acta 77:157–159
May SW, Abbott BJ (1972) Enzymatic epoxidation. I. Alkene epoxidation by the ω-hydroxylation system of Pseudomonas oleovorans. Biochem Biophys Res Commun 48:1230–1234
May SW, Abbott BJ (1973) Enzymatic epoxidation. II. Comparison between the epoxidation and hydroxylation reactions catalyzed by the ω-hydroxylation system of Pseudomonas oleovorans. J Biol Chem 248:1725–1730
May SW, Schwartz RD (1974) Stereoselective epoxidation of octadiene catalyzed by an enzyme system of Pseudomonas oleovorans. J Am Chem Soc 96:4031–4032
Mckenna EJ, Coon MJ (1970) Enzymatic ω-oxidation. IV. Purification and properties of the ω-hydroxylase of Pseudomonas oleovorans. J Biol Chem 245:3882–3889
Ohta H, Tetsukawa H (1978) Microbial epoxidation of long chain terminal olefins. J Chem Soc Chem Commun P850
Patel RN, Hou CT, Laskin AI, Felix A, Derelanko P (1979) Microbial oxidation of gaseous hydrocarbons. II. Hydroxylation of alkanes and epoxidation of alkenes by cell-free particulate fractions of methane-utilizing bacteria. J Bacteriol 139:675–679
Swern D, Billen GN, Scanlan JT (1946) Hydroxylation and epoxidation of some 1-olefins with per-acids. J Am Chem Soc 68:1504–1507
Takahashi J, Kobayashi K, Imada Y, Yamada K (1964) Effect of Corn steep liquor and thiamine on L-glutamic acid fermentation of hydrocarbons. Amino Acid, Nucleic Acid 10:1–5
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Furuhashi, K., Taoka, A., Uchida, S. et al. Production of 1,2-epoxyalkanes from 1-alkenes by Nocardia corallina B-276. European J. Appl. Microbiol. Biotechnol. 12, 39–45 (1981). https://doi.org/10.1007/BF00508117
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DOI: https://doi.org/10.1007/BF00508117