A biotechnological approach to the synthesis of epoxides: Bioconversion of hydrocarbons by <i>Pseudomonas oleovorans</i> during growth in a multiphase system

Smet, M J de

doi:10.1002/bit.260250421

Cited by 9 publications

(3 citation statements)

References 2 publications

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“…Various mono-oxygenases of bacterial origin can however perform such reactions with high regio-and stereoselectivity (de Smet, 1983;Furuhashi, 1992;Katopodis, 1982;Nothe and Hartmans, 1984;Ohta and Tetsukawa, 1978;Wubbolts et al, 1994a).…”

Section: Conclusion Biocatalytic Potential Of Alkane and Xylene Monomentioning

confidence: 98%

Biosynthesis of synthons in two-liquid-phase media

Wubbolts¹,

Favre-Bulle²,

Witholt³

2000

Biotechnol. Bioeng.

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The Pseudomonas oleovorans alkane hydroxylase and xylene oxygenase from Pseudomonas putida are versatile mono‐oxygenases for stereo‐ and regioselective oxidation of aliphatic and aromatic hydrocarbons. Pseudomonas oleovorans and alkanol dehydrogenase deficient mutants of Pseudomonas have previously been used to produce alkanols from various alkanes and optically active epoxides from alkenes. Similarly, P. putida strains have been used to produce aromatic alcohols, aromatic acids, and optically active styrene oxides. A limitation in the use of Pseudomonas strains for bioconversions is that these strains can degrade some of the products formed. To counter this problem, we have constructed Escherichia coli recombinants, which contain the alk genes from the OCT plasmid of P. oleovorans [E. coli HB101 (pGEc47)] and the xylMA genes from the TOL plasmid of P. putida mt‐2 [E. coli HB101 (pGB63)], encoding alkane hydroxylase and xylene oxygenase, respectively. Escherichia coli HB101 (pGEc47) was used to produce octanoic acid from n‐octane and E. coli HB101 (pBG63) was put to use for the oxidation of styrene to styrene oxide in two‐liquid phase biocatalysis at high cell densities. The alk+ recombinant strain E. coli HB101 (pGEc47) was grown to 40 g/L cell dry mass in the presence of n‐octane, which was converted to octanoic acid by the alkane oxidation system, the product accumulating in the aqueous phase. The xyl+ recombinant E. coli HB101 (pBG63) was grown to a cell density of 26 g/L cell dry mass in the presence of around 7% (v/v) n‐dodecane, which contained 2% (v/v) styrene. The recombinant E. coli (xyl+) converted styrene to (S)‐(+)‐styrene oxide at high enantiomeric excess (94% ee) and this compound partitioned almost exclusively into the organic phase. Using these high‐cell‐density two‐liquid‐phase cultures, the products accumulated rapidly, yielding high concentrations of products (50 mM octanoic acid and 90 mM styrene oxide) in the respective phases. © 1996 John Wiley & Sons, Inc.

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Section: Conclusion Biocatalytic Potential Of Alkane and Xylene Monomentioning

confidence: 98%

Biosynthesis of synthons in two-liquid-phase media

Wubbolts¹,

Favre-Bulle²,

Witholt³

2000

Biotechnol. Bioeng.

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“…PHA accumulation is greatest in fluorescent pseudomonads when they grow on decanoate, but accumulation also accurs when they frow on other fatty acids (hydroxy and non-hydroxy), glucose, fructose, and glycerol. P. oleovorans accumulates poly-~-hydroxyoctanoate when gown on C S -C 12 alkanes, l-octene, and CS-C IO alcohols (de Smet et al, 1983). Several investigators have shown that PHA monomer length depends on the growth source.…”

Section: Polyhydroxyalkoanates (Pha)mentioning

confidence: 99%

“…The alkane hydroxylase enzyme from P. oleovorans is capable of regioselective oxidation of terminal methyl groups of linear and branched alkanes and alkylbenzenes (Baptist et al, 1963;de Smet et al, 1983b;van Beilen et al, 1994), stereoselective epoxidation of terminal alkenes (Abbott and Hou, 1973;de Smet, 1983;de Smet et al, 1981;May and Abbott, 1972;May and Schwartz, 1974) and alkadienes (May and Schwartz, 1974), oxidation of alcohols to aldehydes, and demethylation of methylethers and stereospecific sulfoxidation reactions (May and Katopodis, 1986;Katopodis et al, 1984).…”

Section: 12a Monooxygenasesmentioning

confidence: 99%

Pseudomonas

1998

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Enantioselective oxidation by non‐heme iron mono‐oxygenases from Pseudomonas

Wubbolts

Noordman

Beilen

1995

Recl. Trav. Chim. Pays‐Bas

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Abstract. Xylene oxygenase (XO), an enzyme system from Pseudomonas putida mt-2, selectively oxidizes the methyl side group of toluene-derived compounds. The enzyme is related to Pseudomonas oleouorans mono-oxygenase (POM), which has been used to produce optically active epoxides from various alkenes at high enantiomeric excess. We have introduced XO into Escherichia coli and produced variously substituted benzyl alcohols from toluene derivatives and optically active styrene epoxides from styrene, m-and p-chlorostyrene and m-and p-methylstyrene using this biocatalyst. The products of oxidation of styrene and styrene derivatives had enantiomeric excesses (ees) ranging from 37% to over 98%. Similarly, Pseudomonas putida was engineered such that the hydroxylation of compounds by POM could be investigated independent of subsequent product degradation. The biocatalyst accepted a wide range of substrates and oxidized both linear and branched alkanes, and cyclic alkanes as well as alkylbenzenes to the corresponding alcohols. In this review we describe the catalytic potential of engineered biocatalysts based on both XO and POM and discuss the structural and functional similarities of these non-heme iron monooxygenases.

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A biotechnological approach to the synthesis of epoxides: Bioconversion of hydrocarbons by Pseudomonas oleovorans during growth in a multiphase system

Cited by 9 publications

References 2 publications

Biosynthesis of synthons in two-liquid-phase media

Biosynthesis of synthons in two-liquid-phase media

Pseudomonas

Enantioselective oxidation by non‐heme iron mono‐oxygenases from Pseudomonas

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