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Appl Environ Microbiol. Feb 1990; 56(2): 569–571.
PMCID: PMC183381

Biotransformation of substituted benzoates to the corresponding cis-diols by an engineered strain of Pseudomonas oleovorans producing the TOL plasmid-specified enzyme toluate-1,2-dioxygenase.

Abstract

The conversion of substituted benzoates into 1,2-cis-dihydroxycyclohexa-3,5-diene carboxylic acids (cis-diols) was effected by using Escherichia coli and Pseudomonas recombinants carrying the xylXYZ genes originating from the Pseudomonas putida mt-2 TOL plasmid, thus producing toluate-1,2-dioxygenase. Pseudomonas oleovorans GPo12 recombinants readily produced meta- and para-substituted cis-diols, but were limited in their oxidation of ortho-substituted substrates.

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Selected References

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  • Franklin FC, Bagdasarian M, Bagdasarian MM, Timmis KN. Molecular and functional analysis of the TOL plasmid pWWO from Pseudomonas putida and cloning of genes for the entire regulated aromatic ring meta cleavage pathway. Proc Natl Acad Sci U S A. 1981 Dec;78(12):7458–7462. [PMC free article] [PubMed]
  • Harayama S, Lehrbach PR, Timmis KN. Transposon mutagenesis analysis of meta-cleavage pathway operon genes of the TOL plasmid of Pseudomonas putida mt-2. J Bacteriol. 1984 Oct;160(1):251–255. [PMC free article] [PubMed]
  • Harayama S, Mermod N, Rekik M, Lehrbach PR, Timmis KN. Roles of the divergent branches of the meta-cleavage pathway in the degradation of benzoate and substituted benzoates. J Bacteriol. 1987 Feb;169(2):558–564. [PMC free article] [PubMed]
  • Harayama S, Rekik M, Timmis KN. Genetic analysis of a relaxed substrate specificity aromatic ring dioxygenase, toluate 1,2-dioxygenase, encoded by TOL plasmid pWW0 of Pseudomonas putida. Mol Gen Genet. 1986 Feb;202(2):226–234. [PubMed]
  • Inouye S, Nakazawa A, Nakazawa T. Molecular cloning of TOL genes xylB and xylE in Escherichia coli. J Bacteriol. 1981 Mar;145(3):1137–1143. [PMC free article] [PubMed]
  • Inouye S, Nakazawa A, Nakazawa T. Molecular cloning of gene xylS of the TOL plasmid: evidence for positive regulation of the xylDEGF operon by xylS. J Bacteriol. 1981 Nov;148(2):413–418. [PMC free article] [PubMed]
  • Inouye S, Nakazawa A, Nakazawa T. Expression of the regulatory gene xylS on the TOL plasmid is positively controlled by the xylR gene product. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5182–5186. [PMC free article] [PubMed]
  • Kunz DA, Chapman PJ. Catabolism of pseudocumene and 3-ethyltoluene by Pseudomonas putida (arvilla) mt-2: evidence for new functions of the TOL (pWWO) plasmid. J Bacteriol. 1981 Apr;146(1):179–191. [PMC free article] [PubMed]
  • Lehrbach PR, Zeyer J, Reineke W, Knackmuss HJ, Timmis KN. Enzyme recruitment in vitro: use of cloned genes to extend the range of haloaromatics degraded by Pseudomonas sp. strain B13. J Bacteriol. 1984 Jun;158(3):1025–1032. [PMC free article] [PubMed]
  • Mermod N, Lehrbach PR, Reineke W, Timmis KN. Transcription of the TOL plasmid toluate catabolic pathway operon of Pseudomonas putida is determined by a pair of co-ordinately and positively regulated overlapping promoters. EMBO J. 1984 Nov;3(11):2461–2466. [PMC free article] [PubMed]
  • Mermod N, Ramos JL, Lehrbach PR, Timmis KN. Vector for regulated expression of cloned genes in a wide range of gram-negative bacteria. J Bacteriol. 1986 Aug;167(2):447–454. [PMC free article] [PubMed]
  • Neidle EL, Shapiro MK, Ornston LN. Cloning and expression in Escherichia coli of Acinetobacter calcoaceticus genes for benzoate degradation. J Bacteriol. 1987 Dec;169(12):5496–5503. [PMC free article] [PubMed]
  • Ramos JL, Mermod N, Timmis KN. Regulatory circuits controlling transcription of TOL plasmid operon encoding meta-cleavage pathway for degradation of alkylbenzoates by Pseudomonas. Mol Microbiol. 1987 Nov;1(3):293–300. [PubMed]
  • Ramos JL, Stolz A, Reineke W, Timmis KN. Altered effector specificities in regulators of gene expression: TOL plasmid xylS mutants and their use to engineer expansion of the range of aromatics degraded by bacteria. Proc Natl Acad Sci U S A. 1986 Nov;83(22):8467–8471. [PMC free article] [PubMed]
  • Reineke W, Knackmuss HJ. Chemical structure and biodegradability of halogenate aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Biochim Biophys Acta. 1978 Sep 6;542(3):412–423. [PubMed]
  • Reiner AM, Hegeman GD. Metabolism of benzoic acid by bacteria. Accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus. Biochemistry. 1971 Jun 22;10(13):2530–2536. [PubMed]
  • Rojo F, Pieper DH, Engesser KH, Knackmuss HJ, Timmis KN. Assemblage of ortho cleavage route for simultaneous degradation of chloro- and methylaromatics. Science. 1987 Dec 4;238(4832):1395–1398. [PubMed]
  • Schwartz RD, McCoy CJ. Pseudomonas oleovorans hydroxylation-epoxidation system: additional strain improvements. Appl Microbiol. 1973 Aug;26(2):217–218. [PMC free article] [PubMed]
  • VOGEL HJ, BONNER DM. Acetylornithinase of Escherichia coli: partial purification and some properties. J Biol Chem. 1956 Jan;218(1):97–106. [PubMed]
  • Whited GM, McCombie WR, Kwart LD, Gibson DT. Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid. J Bacteriol. 1986 Jun;166(3):1028–1039. [PMC free article] [PubMed]
  • Worsey MJ, Franklin FC, Williams PA. Regulation of the degradative pathway enzymes coded for by the TOL plasmid (pWWO) from Pseudomonas putida mt-2. J Bacteriol. 1978 Jun;134(3):757–764. [PMC free article] [PubMed]
  • Worsey MJ, Williams PA. Metabolism of toluene and xylenes by Pseudomonas (putida (arvilla) mt-2: evidence for a new function of the TOL plasmid. J Bacteriol. 1975 Oct;124(1):7–13. [PMC free article] [PubMed]
  • Zeyer J, Lehrbach PR, Timmis KN. Use of cloned genes of Pseudomonas TOL plasmid to effect biotransformation of benzoates to cis-dihydrodiols and catechols by Escherichia coli cells. Appl Environ Microbiol. 1985 Dec;50(6):1409–1413. [PMC free article] [PubMed]

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