5-Chloropicolinic acid is produced by specific degradation of 4-chlorobenzoic acid by Sphingomonas paucimobilis BPSI-3

Davison, Annette; Jardine, Daniel; Karuso, Peter

doi:10.1038/sj.jim.2900742

Cited by 9 publications

(7 citation statements)

References 22 publications

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“…Chemical conversion of 1,688 M RFP resulted in 931 M 6-phenylacetylene picolinic acid or a 55% yield, which is consistent with yields reported by Asano et al (1) for conversion of 2-hydroxymuconic semialdehyde to picolinic acid under similar conditions. The 6-phenylacetylene picolinic acid was not produced under normal culture conditions, as has been reported for other picolinic acids (3,4,13,29). When 6-phenylacetylene picolinic acid was purified and extracted as described in Materials and Methods, it had a melting point of 138.2 to 139.2°C, accompanied by decomposition.…”

Section: Vol 69 2003 Production Of 6-phenylacetylene Picolinic Acidsupporting

confidence: 48%

“…The freezedried product was recrystallized from hot heptane before NMR experiments and CHN analysis. The RFP could be converted to 6-phenylacetylene picolinate by direct addition of NH 4 OH to the clarified culture medium, but the preliminary SPE step provided a cleaner product and greatly reduced the volume of fluid that had to be treated with NH 4 OH.…”

Section: Methodsmentioning

confidence: 99%

“…The methanol was removed under a vacuum, and the purified RFP was concentrated by freeze-drying. RFP in methanol was converted to 6-phenylacetylene picolinic acid by treatment with 8 N NH 4 OH overnight at 60°C. The pH of the 6-phenylacetylene picolinic acid solution was adjusted to pH 3.6, deionized water was added to reduce the methanol content to less than 25%, and the solution was passed through a C 18 SPE column.…”

Section: Methodsmentioning

confidence: 99%

“…4) Conversion of RFP to 6-phenylacetylene picolinic acid. The purified compound was dissolved in 8 N NH 4 OH and kept overnight at 60°C for conversion to 6-phenylacetylene picolinic acid. Chemical conversion of 1,688 M RFP resulted in 931 M 6-phenylacetylene picolinic acid or a 55% yield, which is consistent with yields reported by Asano et al (1) for conversion of 2-hydroxymuconic semialdehyde to picolinic acid under similar conditions.…”

Section: Vol 69 2003 Production Of 6-phenylacetylene Picolinic Acidmentioning

confidence: 99%

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Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Spain¹,

Nishino²,

Tan

et al. 2003

Appl Environ Microbiol

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Several strategies for using enzymes to catalyze reactions leading to the synthesis of relatively simple substituted picolinic acids have been described. The goal of the work described here was to synthesize a more complex molecule, 6-phenylacetylene picolinic acid [6-(2-phenylethynyl)pyridine-2-carboxylic acid], for use as a potential endcapping agent for aerospace polymers. We screened 139 toluene-degrading strains that use a variety of catabolic pathways for the ability to catalyze oxidative transformation of diphenylacetylene. Acinetobacter sp. strain F4 catalyzed the overall conversion of diphenylacetylene to a yellow metabolite, which was identified as a putative meta ring fission product (2-hydroxy-8-phenyl-6-oxoocta-2,4-dien-7-ynoic acid [RFP]). The activity could be sustained by addition of toluene at a flow rate determined empirically so that the transformations were sustained in spite of the fact that toluene is a competitive inhibitor of the enzymes. The overall rate of transformation was limited by the instability of RFP. The RFP was chemically converted to 6-phenylacetylene picolinic acid by treatment with ammonium hydroxide. The results show the potential for using the normal growth substrate to provide energy and to maintain induction of the enzymes involved in biotransformation during preliminary stages of biocatalyst development.Substituted picolinic acids are used as feedstocks for the synthesis of a variety of pharmaceuticals, agricultural chemicals, and dyes (1, 12). Chemical synthesis involves several steps and the use of harsh reagents, and low yields of the desired products are obtained. Several strategies for using enzymes to catalyze reactions leading to the synthesis of picolinic acid have been described. The first reports (3, 29) described production of 2-hydroxymuconic semialdehyde from catechol catalyzed by dioxygenase enzymes from two strains of gram-negative bacteria. Treatment of the 2-hydroxymuconic semialdehyde with ammonium ions led to the formation of picolinic acid. This reaction has been the basis for a number of subsequent papers (1) and patents (11,12) describing the synthesis of substituted picolinic acids. Recently, a related strategy involving cleavage of the ring of substituted 2-aminophenols by aminophenol dioxygenase from Pseudomonas pseudoalcaligenes strain JS 45 was described (16). The resultant ring fission product rearranges spontaneously to the corresponding picolinic acid. The techniques described above have been used for synthesis of relatively simple substituted picolinic acids. The goal of the work described here was to synthesize a more complex molecule, 6-phenylacetylene picolinic acid [6-(2-phenylethynyl)pyridine-2-carboxylic acid]. The potential reactivity of 6-phenylacetylene picolinate as a cross-linker or a dienophile makes it a good candidate to replace phenylacetylenes as endcapping agents for high-performance thermosetting polymers for aerospace applications (17) and electronic packaging (26). The strong electron-withdrawing properties of the pyri...

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Section: Vol 69 2003 Production Of 6-phenylacetylene Picolinic Acidsupporting

confidence: 48%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Vol 69 2003 Production Of 6-phenylacetylene Picolinic Acidmentioning

confidence: 99%

See 2 more Smart Citations

Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Spain¹,

Nishino²,

Tan

et al. 2003

Appl Environ Microbiol

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show abstract

“…As a consequence, these strains encounter the problem of misrouting halogenated metabolites into unproductive catabolic pathways, forming toxic compounds, such as protoanemonin, or accumulating toxic halogenated deadend products, such as halosalicylates, halocatechols and others (Bartels et al, 1984;Blasco et al, 1997;Davison et al, 1999;Camara et al, 2004;Pieper, 2005).…”

Section: Introductionmentioning

confidence: 99%

Growth of the genetically engineered strain Cupriavidus necator RW112 with chlorobenzoates and technical chlorobiphenyls

Wittich

Wolff

2007

Microbiology

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Cupriavidus necator (formerly Ralstonia eutropha) strain H850 is known to grow on biphenyl, and to co-oxidize congeners of polychlorinated biphenyls (PCBs). Using a Tn5-based minitransposon shuttle system and the TOL plasmid, the rational construction of hybrids of H850 was achieved by subsequent introduction of three distinct elements carrying 11 catabolic loci from three other biodegrading bacteria into the parent strain, finally yielding C. necator RW112. The new genetic elements introduced into H850 and its derivatives were tcbRCDEF, which encode the catabolic enzymes needed for chlorocatechol biodegradation under the control of a transcriptional regulator, followed by cbdABC, encoding a 2-halobenzoate dioxygenase, and xylXYZ, encoding a broad-spectrum toluate dioxygenase. The expression of the introduced genes was demonstrated by measuring the corresponding enzymic activities. The engineered strain RW112 gained the ability to grow on all isomeric monochlorobenzoates and 3,5-dichlorobenzoate, all monochlorobiphenyls, and 3,5-dichloro-, 2,39-dichloro-and 2,49-dichlorobiphenyl, without accumulation of chlorobenzoates. It also grew and utilized two commercial PCB formulations, Aroclor 1221 and Aroclor 1232, as sole carbon and energy sources for growth. This is the first report on the aerobic growth of a genetically improved bacterial strain at the expense of technical Aroclor mixtures.

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Diversity of Dechlorinating Bacteria

et al. 2004

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5-Chloropicolinic acid is produced by specific degradation of 4-chlorobenzoic acid by Sphingomonas paucimobilis BPSI-3

Cited by 9 publications

References 22 publications

Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Growth of the genetically engineered strain Cupriavidus necator RW112 with chlorobenzoates and technical chlorobiphenyls

Diversity of Dechlorinating Bacteria

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