Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids

The p-cumate-degrading strain Pseudomonas putida F1 and the m- and p-toluate-degrading strain P. putida mt-2 transform indole-2-carboxylate and indole-3-carboxylate to colored products identified here as indigo, indirubin, and isatin. A mechanism by which these products could be formed spontaneously following dioxygenase-catalyzed dihydroxylation of the indolecarboxylates is proposed. Indolecarboxylates were employed as chromogenic substrates for identifying recombinant bacteria carrying genes encoding p-cumate dioxygenase and toluate dioxygenase. Dioxygenase gene-carrying bacteria could be readily distinguished as dark green-blue colonies among other colorless recombinant Escherichia coli colonies on selective agar plates containing either indole-2-carboxylate or indole-3-carboxylate.

[1]  T. Iida,et al.  Cloning and characterization of a chromosomal gene cluster, pah, that encodes the upper pathway for phenanthrene and naphthalene utilization by Pseudomonas putida OUS82 , 1994, Journal of bacteriology.

[2]  M. Shiaris,et al.  Metabolism of naphthalene, fluorene, and phenanthrene: preliminary characterization of a cloned gene cluster from Pseudomonas putida NCIB 9816 , 1994, Journal of bacteriology.

[3]  W. Suen,et al.  Cloning and characterization of Pseudomonas sp. strain DNT genes for 2,4-dinitrotoluene degradation , 1993, Journal of bacteriology.

[4]  B. Ensley,et al.  Construction of Metabolic Operons Catalyzing the De Novo Biosynthesis of Indigo in Escherichia coli , 1993, Bio/Technology.

[5]  P. Chapman,et al.  Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions , 1992, Journal of bacteriology.

[6]  D. Parke.  Application of p-Toluidine in Chromogenic Detection of Catechol and Protocatechuate, Diphenolic Intermediates in Catabolism of Aromatic Compounds , 1992, Applied and environmental microbiology.

[7]  P. Chapman,et al.  Characterization of Pseudomonas putida mutants unable to catabolize benzoate: cloning and characterization of Pseudomonas genes involved in benzoate catabolism and isolation of a chromosomal DNA fragment able to substitute for xylS in activation of the TOL lower-pathway promoter , 1992, Journal of bacteriology.

[8]  D. R. Woods,et al.  Identification of indigo-related pigments produced by Escherichia coli containing a cloned Rhodococcus gene. , 1992, Journal of general microbiology.

[9]  J. Karns,et al.  Cloning and analysis of s-triazine catabolic genes from Pseudomonas sp. strain NRRLB-12227 , 1991, Journal of bacteriology.

[10]  S. Assinder,et al.  The TOL plasmids: determinants of the catabolism of toluene and the xylenes. , 1990, Advances in microbial physiology.

[11]  G. Stephens,et al.  Cloning and expression in Escherichia coli of the toluene dioxygenase gene from Pseudomonas putida NCIB11767. , 1989, FEMS microbiology letters.

[12]  C. A. Fewson.  Microbial metabolism of mandelate: a microcosm of diversity. , 1988, FEMS microbiology reviews.

[13]  D. Ballou,et al.  Purification and characterization of phthalate oxygenase and phthalate oxygenase reductase from Pseudomonas cepacia. , 1987, The Journal of biological chemistry.

[14]  P. Williams,et al.  Gene organization of the first catabolic operon of TOL plasmid pWW53: production of indigo by the xylA gene product , 1987, Journal of bacteriology.

[15]  K. Timmis,et al.  Characterization of a plasmid-specified pathway for catabolism of isopropylbenzene in Pseudomonas putida RE204 , 1986, Journal of bacteriology.

[16]  D. Gibson,et al.  Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid , 1986, Journal of bacteriology.

[17]  K. N. Timmis,et al.  New Route to Bacterial Production of Indigo , 1986, Bio/Technology.

[18]  S. Harayama,et al.  Transposon mutagenesis analysis of meta-cleavage pathway operon genes of the TOL plasmid of Pseudomonas putida mt-2 , 1984, Journal of bacteriology.

[19]  Lawrence P. Wackett,et al.  Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. , 1983, Science.

[20]  P. Chapman,et al.  Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli , 1983, Journal of bacteriology.

[21]  G. Humphreys,et al.  Expression of the Eco RI restriction-modification system and the construction of positive-selection cloning vectors. , 1982, Gene.

[22]  D. W. Ribbons,et al.  Metabolism of dibutylphthalate and phthalate by Micrococcus sp. strain 12B , 1982, Journal of bacteriology.

[23]  D. W. Ribbons,et al.  The transformation of phthalaldehydate by phthalate-grown Micrococcus strain 12B. , 1982, Archives of biochemistry and biophysics.

[24]  D. Botstein,et al.  Advanced bacterial genetics , 1980 .

[25]  R. H. Olsen,et al.  Isolation of large bacterial plasmids and characterization of the P2 incompatibility group plasmids pMG1 and pMG5 , 1978, Journal of bacteriology.

[26]  H. Kiyohara,et al.  The Catabolism of Phenanthrene and Naphthalene by Bacteria , 1978 .

[27]  D. W. Ribbons,et al.  p-cymene pathway in Pseudomonas putida: initial reactions , 1977, Journal of bacteriology.

[28]  D. W. Ribbons,et al.  p-Cymene pathway in Pseudomonas putida: ring cleavage of 2,3-dihydroxy-p-cumate and subsequent reactions , 1977, Journal of bacteriology.

[29]  D. W. Ribbons,et al.  The p-cymene pathway in Pseudomonas putida PL: isolation of a dihydrodiol accumulated by a mutant. , 1976, Biochemical and biophysical research communications.

[30]  H. Kiyohara,et al.  Degradation of Phenanthrene througho-Phthalate by anAeromonassp. , 1976 .

[31]  H. Kiyohara,et al.  Degradation of Phenanthrene through o-Phthalate by an Aeromonas sp. , 1976 .

[32]  P. Williams,et al.  Metabolism of toluene and xylenes by Pseudomonas (putida (arvilla) mt-2: evidence for a new function of the TOL plasmid , 1975, Journal of bacteriology.

[33]  F. Sariaslani,et al.  Microbial degradation of hydrocarbons. Catabolism of 1-phenylalkanes by Nocardia salmonicolor. , 1974, The Biochemical journal.

[34]  A. Reiner.  Metabolism of Benzoic Acid by Bacteria: 3,5- Cyclohexadiene-1,2-Diol-1-Carboxylic Acid Is an Intermediate in the Formation of Catechol , 1971, Journal of bacteriology.

[35]  G. Hegeman,et al.  Metabolism of benzoic acid by bacteria. Accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus. , 1971, Biochemistry.

[36]  P. Chapman,et al.  The Microbial Oxidation of Aromatic Hydrocarbons , 1971 .

[37]  D. Gibson,et al.  Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida. , 1970, Biochemistry.

[38]  D. Gibson,et al.  The metabolism of cresols by species of Pseudomonas. , 1966, The Biochemical journal.

[39]  T. Iida,et al.  Cloning and characterization of a chromosomal gene cluster, pah, that encodes the upper pathway for phenanthrene and naphthalene utilization by Pseudomonas putida OUS82 , 1994, Journal of bacteriology.

[40]  M. Shiaris,et al.  Metabolism of naphthalene, fluorene, and phenanthrene: preliminary characterization of a cloned gene cluster from Pseudomonas putida NCIB 9816 , 1994, Journal of bacteriology.

[41]  W. Suen,et al.  Cloning and characterization of Pseudomonas sp. strain DNT genes for 2,4-dinitrotoluene degradation , 1993, Journal of bacteriology.

[42]  B. Ensley,et al.  Construction of Metabolic Operons Catalyzing the De Novo Biosynthesis of Indigo in Escherichia coli , 1993, Bio/Technology.

[43]  P. Chapman,et al.  Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions , 1992, Journal of bacteriology.

[44]  D. Parke.  Application of p-Toluidine in Chromogenic Detection of Catechol and Protocatechuate, Diphenolic Intermediates in Catabolism of Aromatic Compounds , 1992, Applied and environmental microbiology.

[45]  P. Chapman,et al.  Characterization of Pseudomonas putida mutants unable to catabolize benzoate: cloning and characterization of Pseudomonas genes involved in benzoate catabolism and isolation of a chromosomal DNA fragment able to substitute for xylS in activation of the TOL lower-pathway promoter , 1992, Journal of bacteriology.

[46]  D. R. Woods,et al.  Identification of indigo-related pigments produced by Escherichia coli containing a cloned Rhodococcus gene. , 1992, Journal of general microbiology.

[47]  J. Karns,et al.  Cloning and analysis of s-triazine catabolic genes from Pseudomonas sp. strain NRRLB-12227 , 1991, Journal of bacteriology.

[48]  S. Assinder,et al.  The TOL plasmids: determinants of the catabolism of toluene and the xylenes. , 1990, Advances in microbial physiology.

[49]  G. Stephens,et al.  Cloning and expression in Escherichia coli of the toluene dioxygenase gene from Pseudomonas putida NCIB11767. , 1989, FEMS microbiology letters.

[50]  H. Lehväslaiho,et al.  Cloning, nucleotide sequence and characterization of genes encoding naphthalene dioxygenase of Pseudomonas putida strain NCIB9816. , 1988, Gene.

[51]  C. A. Fewson.  Microbial metabolism of mandelate: a microcosm of diversity. , 1988, FEMS microbiology reviews.

[52]  H. A. Sancovich,et al.  The isolation and identification of indigoid pigments from urine. , 1988, Clinica chimica acta; international journal of clinical chemistry.

[53]  D. Ballou,et al.  Purification and characterization of phthalate oxygenase and phthalate oxygenase reductase from Pseudomonas cepacia. , 1987, The Journal of biological chemistry.

[54]  P. Williams,et al.  Gene organization of the first catabolic operon of TOL plasmid pWW53: production of indigo by the xylA gene product , 1987, Journal of bacteriology.

[55]  K. Timmis,et al.  Characterization of a plasmid-specified pathway for catabolism of isopropylbenzene in Pseudomonas putida RE204 , 1986, Journal of bacteriology.

[56]  D. Gibson,et al.  Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid , 1986, Journal of bacteriology.

[57]  K. N. Timmis,et al.  New Route to Bacterial Production of Indigo , 1986, Bio/Technology.

[58]  S. Harayama,et al.  Transposon mutagenesis analysis of meta-cleavage pathway operon genes of the TOL plasmid of Pseudomonas putida mt-2 , 1984, Journal of bacteriology.

[59]  Lawrence P. Wackett,et al.  Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. , 1983, Science.

[60]  P. Chapman,et al.  Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli , 1983, Journal of bacteriology.

[61]  G. Humphreys,et al.  Expression of the Eco RI restriction-modification system and the construction of positive-selection cloning vectors. , 1982, Gene.

[62]  D. W. Ribbons,et al.  Metabolism of dibutylphthalate and phthalate by Micrococcus sp. strain 12B , 1982, Journal of bacteriology.

[63]  D. W. Ribbons,et al.  The transformation of phthalaldehydate by phthalate-grown Micrococcus strain 12B. , 1982, Archives of biochemistry and biophysics.

[64]  D. Botstein,et al.  Advanced bacterial genetics , 1980 .

[65]  R. H. Olsen,et al.  Isolation of large bacterial plasmids and characterization of the P2 incompatibility group plasmids pMG1 and pMG5 , 1978, Journal of bacteriology.

[66]  H. Kiyohara,et al.  The Catabolism of Phenanthrene and Naphthalene by Bacteria , 1978 .

[67]  D. W. Ribbons,et al.  p-cymene pathway in Pseudomonas putida: initial reactions , 1977, Journal of bacteriology.

[68]  D. W. Ribbons,et al.  p-Cymene pathway in Pseudomonas putida: ring cleavage of 2,3-dihydroxy-p-cumate and subsequent reactions , 1977, Journal of bacteriology.

[69]  D. W. Ribbons,et al.  The p-cymene pathway in Pseudomonas putida PL: isolation of a dihydrodiol accumulated by a mutant. , 1976, Biochemical and biophysical research communications.

[70]  H. Kiyohara,et al.  Degradation of Phenanthrene through o-Phthalate by an Aeromonas sp. , 1976 .

[71]  P. Williams,et al.  Metabolism of toluene and xylenes by Pseudomonas (putida (arvilla) mt-2: evidence for a new function of the TOL plasmid , 1975, Journal of bacteriology.

[72]  F. Sariaslani,et al.  Microbial degradation of hydrocarbons. Catabolism of 1-phenylalkanes by Nocardia salmonicolor. , 1974, The Biochemical journal.

[73]  A. Reiner.  Metabolism of Benzoic Acid by Bacteria: 3,5- Cyclohexadiene-1,2-Diol-1-Carboxylic Acid Is an Intermediate in the Formation of Catechol , 1971, Journal of bacteriology.

[74]  G. Hegeman,et al.  Metabolism of benzoic acid by bacteria. Accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus. , 1971, Biochemistry.

[75]  D. Gibson,et al.  Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida. , 1970, Biochemistry.

[76]  D. Gibson,et al.  The metabolism of cresols by species of Pseudomonas. , 1966, The Biochemical journal.