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Chemical Compound Review:

AG-F-69761 2-hydroxypenta-2,4-dienoic acid

Synonyms: CTK4J2671, AC1L2T2K, 50480-68-7, 2-Hydroxy-2,4-pentadienoic acid, 2,4-Pentadienoic acid,2-hydroxy-

Duffner, F.M. et al., Nojiri, H. et al., Eaton, R.W., Bayly, R.C. et al., Sakai, M. et al., et al.

Duffner, Kirchner, Bauer, Müller,

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Disease relevance of C00596

Growth on phenol of two strains of Pseudomonas putida biotype A, NCIB 10015 and NCIB 9865, elicits the synthesis of an enzyme that hydrolyzes 2-hydroxy-6-oxo-2,4-heptadienoate to 2-oxopent-4-enoate [1].
A gram-positive polychlorinated biphenyl (PCB) degrader, Rhodococcus sp. strain RHA1, metabolizes biphenyl through the 2-hydroxypenta-2,4-dienoate (HPD) and benzoate metabolic pathways [2].

High impact information on C00596

2-Keto-4-pentenoate is in rapid equilibrium with 2-hydroxy-2,4-pentadienoate, which is also a strong noncovalent inhibitor of D-amino-acid oxidase [3].
Thirty-two open reading frames (ORFs) were identified, and the car gene cluster was consequently revealed to consist of 10 genes (carAaAaBaBbCAcAdDFE) encoding the enzymes for the three-step conversion of carbazole to anthranilate and the degradation of 2-hydroxypenta-2,4-dienoate [4].
Based on sequence identity, pheD and pheE were deduced to encode the 2-hydroxypenta-2,4-dienoate hydratase (2HDH), demonstrating 45% amino acid identity to the gene product of cumE from Pseudomonas fluorescens and the acetaldehyde dehydrogenase (acylating) demonstrating 57% amino acid identity to the gene product of bphJ from Pseudomonas LB400 [5].
The next four genes, cmtEFHG, encode 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase, 2-hydroxypenta-2,4-dienoate hydratase, 4-hydroxy-2-oxovalerate aldolase, and acetaldehyde dehydrogenase, respectively, which transform the decarboxylation product to amphibolic intermediates [6].
The todFC1C2BADE gene cluster in Pseudomonas putida F1 encodes enzymes for the first four steps of toluene degradation, leading to the formation of 2-hydroxypenta-2,4-dienoate (HPD) [7].

Biological context of C00596

The product of decarboxylation was 2-hydroxypent-2,4-dienoate rather than its keto form, 2-oxopent-4-enoate [8].

References

Purification and properties of 2-hydroxy-6-oxo-2,4-heptadienoate hydrolase from two strains of Pseudomonas putida. Bayly, R.C., di Berardino, D. J. Bacteriol. (1978) [Pubmed]
2-Hydroxypenta-2,4-dienoate metabolic pathway genes in a strong polychlorinated biphenyl degrader, Rhodococcus sp. strain RHA1. Sakai, M., Miyauchi, K., Kato, N., Masai, E., Fukuda, M. Appl. Environ. Microbiol. (2003) [Pubmed]
Sequence of reactions which follows enzymatic oxidation of allylglycine. Marcotte, P., Walsh, C. Biochemistry (1978) [Pubmed]
Genetic characterization and evolutionary implications of a car gene cluster in the carbazole degrader Pseudomonas sp. strain CA10. Nojiri, H., Sekiguchi, H., Maeda, K., Urata, M., Nakai, S., Yoshida, T., Habe, H., Omori, T. J. Bacteriol. (2001) [Pubmed]
Phenol/cresol degradation by the thermophilic Bacillus thermoglucosidasius A7: cloning and sequence analysis of five genes involved in the pathway. Duffner, F.M., Kirchner, U., Bauer, M.P., Müller, R. Gene (2000) [Pubmed]
p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon. Eaton, R.W. J. Bacteriol. (1996) [Pubmed]
Sequence and expression of the todGIH genes involved in the last three steps of toluene degradation by Pseudomonas putida F1. Lau, P.C., Bergeron, H., Labbé, D., Wang, Y., Brousseau, R., Gibson, D.T. Gene (1994) [Pubmed]
Physically associated enzymes produce and metabolize 2-hydroxy-2,4-dienoate, a chemically unstable intermediate formed in catechol metabolism via meta cleavage in Pseudomonas putida. Harayama, S., Rekik, M., Ngai, K.L., Ornston, L.N. J. Bacteriol. (1989) [Pubmed]

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