IntEnz - EC 1.14.14.9

EC 1 - Oxidoreductases

EC 1.14 - Acting on paired donors, with incorporation or reduction of molecular oxygen. The oxygen incorporated need not be derived from O₂

EC 1.14.14 - With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen

EC 1.14.14.9 - 4-hydroxyphenylacetate 3-monooxygenase

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IntEnz Enzyme Nomenclature
EC 1.14.14.9

Names

Accepted name:

4-hydroxyphenylacetate 3-monooxygenase

Other names:

4 HPA 3-hydroxylase
4-hydroxyphenylacetic acid-3-hydroxylase
p-hydroxyphenylacetate 3-hydroxylase
p-hydroxyphenylacetate hydroxylase
p-hydroxyphenylacetate hydroxylase (FAD)
p-hydroxyphenylacetate 3-hydroxylase (FAD)
HpaB

Systematic name:

4-hydroxyphenylacetate,FAD:oxygen oxidoreductase (3-hydroxylating)

Reaction

30595 [IUBMB]

4-hydroxyphenylacetate

4-hydroxyphenylacetate

Name origin: UniProt - CHECKED (C)

CHEBI:48999

Formula: C8H7O3
Charge: -1

ChEBI compound status: CHECKED (C)

+

FADH₂

FADH2

Name origin: UniProt - CHECKED (C)

CHEBI:58307

Formula: C27H33N9O15P2
Charge: -2

ChEBI compound status: CHECKED (C)

+

O₂

O2

Name origin: UniProt - CHECKED (C)

CHEBI:15379

Formula: O2
Charge: 0

ChEBI compound status: CHECKED (C)

=

3,4-dihydroxyphenylacetate

3,4-dihydroxyphenylacetate

Name origin: UniProt - CHECKED (C)

CHEBI:17612

Formula: C8H7O4
Charge: -1

ChEBI compound status: CHECKED (C)

+

FAD

FAD

Name origin: UniProt - CHECKED (C)

CHEBI:57692

Formula: C27H30N9O15P2
Charge: -3

ChEBI compound status: CHECKED (C)

+

H⁺

H(+)

Name origin: UniProt - CHECKED (C)

CHEBI:15378

Formula: H
Charge: 1

ChEBI compound status: CHECKED (C)

+

H₂O

H2O

Name origin: UniProt - CHECKED (C)

CHEBI:15377

Formula: H2O
Charge: 0

ChEBI compound status: CHECKED (C)

Cofactor

Comments:

The enzyme from Escherichia coli attacks a broad spectrum of phenolic compounds. The enzyme uses FADH2 as a substrate rather than a cofactor [4]. FADH2 is provided by EC 1.5.1.36, flavin reductase (NADH) [5,6].

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UM-BBD , UniPathway

Structural data: CSA , EC2PDB

Gene Ontology: GO:0052881

CAS Registry Number: 37256-71-6

UniProtKB/Swiss-Prot:

Q57160

HPAB_ECOLX

Q48440

HPAB_KLEOX

Q9HWT7

HPAB_PSEAE

Q5SJP8

HPAB_THET8

Q6Q272

HPAH_ACIBA

Q4L1M7

HPAH_GEOP9

A4IT51

HPAH_GEOTN

C0SPC0

YOAI_BACSU

References

Adachi, K., Takeda, Y., Senoh, S. and Kita, H.

Metabolism of p-hydroxyphenylacetic acid in Pseudomonas ovalis.

Biochim. Biophys. Acta 93 : 483-493 (1964).
Prieto, M. A., Perez-Aranda, A., Garcia, J. L.

Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range.

J. Bacteriol. 175 : 2162-2167 (1993). [PMID: 8458860]
Prieto, M. A., Garcia, J. L.

Molecular characterization of 4-hydroxyphenylacetate 3-hydroxylase of Escherichia coli. A two-protein component enzyme.

J. Biol. Chem. 269 : 22823-22829 (1994). [PMID: 8077235]
Xun, L., Sandvik, E. R.

Characterization of 4-hydroxyphenylacetate 3-hydroxylase (HpaB) of Escherichia coli as a reduced flavin adenine dinucleotide-utilizing monooxygenase.

Appl. Environ. Microbiol. 66 : 481-486 (2000). [PMID: 10653707]
Galan, B., Diaz, E., Prieto, M. A., Garcia, J. L.

Functional analysis of the small component of the 4-hydroxyphenylacetate 3-monooxygenase of Escherichia coli W: a prototype of a new flavin:NAD(P)H reductase subfamily.

J. Bacteriol. 182 : 627-636 (2000). [PMID: 10633095]
Louie, T. M., Xie, X. S., Xun, L.

Coordinated production and utilization of FADH₂ by NAD(P)H-flavin oxidoreductase and 4-hydroxyphenylacetate 3-monooxygenase.

Biochemistry 42 : 7509-7517 (2003). [PMID: 12809507]

[EC 1.14.14.9 created 1972 as EC 1.14.13.3, transferred 2011 to EC 1.14.14.9]