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Chemical Compound Review:

AG-K-78902 6-oxopyran-2,4-dicarboxylic acid

Synonyms: SureCN1843937, CHEBI:17872, CTK2H9842, AR-1E4626, AC1L193A, ...

Hara, H. et al., Maruyama, K. et al., Maruyama, K. et al., Otsuka, Y. et al., Maruyama, K., et al.

Maruyama, Shibayama, Ichikawa, Sakou, Yamada, Sugisaki, Masai, Momose, Hara, Nishikawa, Katayama, Fukuda, Maruyama, Miwa, Tsujii, Nagai, Tomita, Harada, Sobajima, Sugisaki,

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Disease relevance of C03671

2-pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species [1].
Sphingomonas paucimobilis SYK-6, which can degrade various low molecular weight compounds derived from plant polyphenols such as lignin, lignan, and tannin, metabolizes these substances via 2-pyrone-4,6-dicarboxylic acid (PDC) [2].

High impact information on C03671

In the 10.5-kb EcoRI fragment carrying the genes for PCA 4,5-dioxygenase (ligAB), 2-pyrone-4,6-dicarboxylate hydrolase (ligI), 4-oxalomesaconate hydratase (ligJ), and a part of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase (ligC), we found the ligK gene, which encodes 4-carboxy-4-hydroxy-2-oxoadipate (CHA) aldolase [3].
The optimum pHs are 8.5 and 6.0 for hydrolysis and synthesis of 2-pyrone-4,6-dicarboxylate, respectively [4].
The 2-pyrone-4,6-dicarboxylate lactonase gene (proL), the protocatechuate 4,5-dioxygenase alpha and beta subunits genes (proOa and proOb), and the 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase gene (proD) were cloned from the chromosomal DNA of Pseudomonas ochraceae NGJ1 [5].
The genes encoding a putative transporter and a 4-oxalomesaconate hydratase were upstream, and a 3'-truncated gene encoding 2-pyrone-4,6-dicarboxylate lactonase was downstream from the proA gene in the same orientation on the DNA fragment [6].

Biological context of C03671

CHMS is the 4,5-cleavage product of PCA and is converted into 2-pyrone-4,6-dicarboxylate (PDC) by LigC [7].

References

2-pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species. Kersten, P.J., Dagley, S., Whittaker, J.W., Arciero, D.M., Lipscomb, J.D. J. Bacteriol. (1982) [Pubmed]
Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function. Otsuka, Y., Nakamura, M., Shigehara, K., Sugimura, K., Masai, E., Ohara, S., Katayama, Y. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
Characterization of the 4-carboxy-4-hydroxy-2-oxoadipate aldolase gene and operon structure of the protocatechuate 4,5-cleavage pathway genes in Sphingomonas paucimobilis SYK-6. Hara, H., Masai, E., Miyauchi, K., Katayama, Y., Fukuda, M. J. Bacteriol. (2003) [Pubmed]
Purification and properties of 2-pyrone-4,6-dicarboxylate hydrolase. Maruyama, K. J. Biochem. (1983) [Pubmed]
Cloning and characterization of the genes encoding enzymes for the protocatechuate meta-degradation pathway of Pseudomonas ochraceae NGJ1. Maruyama, K., Shibayama, T., Ichikawa, A., Sakou, Y., Yamada, S., Sugisaki, H. Biosci. Biotechnol. Biochem. (2004) [Pubmed]
Cloning, sequencing, and expression of the gene encoding 4-hydroxy-4-methyl-2-oxoglutarate aldolase from Pseudomonas ochraceae NGJ1. Maruyama, K., Miwa, M., Tsujii, N., Nagai, T., Tomita, N., Harada, T., Sobajima, H., Sugisaki, H. Biosci. Biotechnol. Biochem. (2001) [Pubmed]
Genetic and biochemical characterization of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase and its role in the protocatechuate 4,5-cleavage pathway in Sphingomonas paucimobilis SYK-6. Masai, E., Momose, K., Hara, H., Nishikawa, S., Katayama, Y., Fukuda, M. J. Bacteriol. (2000) [Pubmed]

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