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1.3.1.87

Accepted name:

3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate dehydrogenase

Reaction:

(1) 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD⁺ = 3-(2,3-dihydroxyphenyl)propanoate + NADH + H⁺
(2) (2E)-3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate + NAD⁺ = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NADH + H⁺

For diagram of 3-phenylpropanoate catabolism, click here and for diagram of cinnamate catabolism, click here

Glossary:

(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate = trans-2,3-dihydroxycinnamate

Other name(s):

hcaB (gene name); cis-dihydrodiol dehydrogenase; 2,3-dihydroxy-2,3-dihydro-phenylpropionate dehydrogenase

Systematic name:

3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate:NAD⁺ oxidoreductase

Comments:

This enzyme catalyses a step in the pathway of phenylpropanoid compounds degradation.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc

References:

1.	Díaz, E., Ferrández, A. and García, J.L. Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. J. Bacteriol. 180 (1998) 2915–2923. [PMID: 9603882]

[EC 1.3.1.87 created 2011]

1.13.11.16

Accepted name:

3-carboxyethylcatechol 2,3-dioxygenase

Reaction:

(1) 3-(2,3-dihydroxyphenyl)propanoate + O₂ = (2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate
(2) (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + O₂ = (2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate

For diagram of 3-phenylpropanoate catabolism, click here and for diagram of cinnamate catabolism, click here

Glossary:

(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate = trans-2,3-dihydroxycinnamate

Other name(s):

2,3-dihydroxy-β-phenylpropionic dioxygenase; 2,3-dihydroxy-β-phenylpropionate oxygenase; 3-(2,3-dihydroxyphenyl)propanoate:oxygen 1,2-oxidoreductase; 3-(2,3-dihydroxyphenyl)propanoate:oxygen 1,2-oxidoreductase (decyclizing)

Systematic name:

3-(2,3-dihydroxyphenyl)propanoate:oxygen 1,2-oxidoreductase (ring-opening)

Comments:

An iron protein. This enzyme catalyses a step in the pathway of phenylpropanoid compounds degradation.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 105503-63-7

References:

1.	Dagley, S., Chapman, P.J. and Gibson, D.T. The metabolism of β-phenylpropionic acid by an Achromobacter. Biochem. J. 97 (1965) 643–650. [PMID: 5881653]
2.	Lam, W. W. Y and Bugg, T. D. H. Chemistry of extradiol aromatic ring cleavage: isolation of a stable dienol ring fission intermediate and stereochemistry of its enzymatic hydrolytic clevage. J. Chem. Soc., Chem. Commun. 10 (1994) 1163–1164.
3.	Díaz, E., Ferrández, A. and García, J.L. Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. J. Bacteriol. 180 (1998) 2915–2923. [PMID: 9603882]

[EC 1.13.11.16 created 1972, modified 2011, modified 2012]

1.14.12.19

Accepted name:

3-phenylpropanoate dioxygenase

Reaction:

(1) 3-phenylpropanoate + NADH + H⁺ + O₂ = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD⁺
(2) (2E)-3-phenylprop-2-enoate + NADH + H⁺ + O₂ = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NAD⁺

For diagram of reaction, click here

Glossary:

(2E)-3-phenylprop-2-enoate = trans-cinnamate
(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate = trans-2,3-dihydroxycinnamate

Other name(s):

HcaA1A2CD; Hca dioxygenase; 3-phenylpropionate dioxygenase

Systematic name:

3-phenylpropanoate,NADH:oxygen oxidoreductase (2,3-hydroxylating)

Comments:

This enzyme catalyses a step in the pathway of phenylpropanoid compounds degradation. It catalyses the insertion of both atoms of molecular oxygen into positions 2 and 3 of the phenyl ring of 3-phenylpropanoate or (2E)-3-phenylprop-2-enoate.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc

References:

1.	Díaz, E., Ferrández, A. and García, J.L. Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. J. Bacteriol. 180 (1998) 2915–2923. [PMID: 9603882]
2.	Burlingame, R. and Chapman, P.J. Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli. J. Bacteriol. 155 (1983) 113–121. [PMID: 6345502]

[EC 1.14.12.19 created 2005, modified 2011]

1.14.13.127

Accepted name:

3-(3-hydroxyphenyl)propanoate hydroxylase

Reaction:

(1) 3-(3-hydroxyphenyl)propanoate + NADH + H⁺ + O₂ = 3-(2,3-dihydroxyphenyl)propanoate + H₂O + NAD⁺
(2) (2E)-3-(3-hydroxyphenyl)prop-2-enoate + NADH + H⁺ + O₂ = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + H₂O + NAD⁺

Glossary:

3-hydroxycinnamate = 3-coumarate = 3-(3-hydroxyphenyl)prop-2-enoate

Other name(s):

mhpA (gene name)

Systematic name:

3-(3-hydroxyphenyl)propanoate,NADH:oxygen oxidoreductase (2-hydroxylating)

Comments:

A flavoprotein (FAD). This enzyme participates in a meta-cleavage pathway employed by the bacterium Escherichia coli for the degradation of various phenylpropanoid compounds.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Burlingame, R. and Chapman, P.J. Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli. J. Bacteriol. 155 (1983) 113–121. [PMID: 6345502]
2.	Burlingame, R.P., Wyman, L. and Chapman, P.J. Isolation and characterization of Escherichia coli mutants defective for phenylpropionate degradation. J. Bacteriol. 168 (1986) 55–64. [DOI] [PMID: 3531186]
3.	Ferrández, A., García, J.L. and Díaz, E. Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12. J. Bacteriol. 179 (1997) 2573–2581. [DOI] [PMID: 9098055]
4.	Díaz, E., Ferrández, A. and García, J.L. Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. J. Bacteriol. 180 (1998) 2915–2923. [PMID: 9603882]

[EC 1.14.13.127 created 2011]