Information on EC 1.14.13.63 - 3-hydroxyphenylacetate 6-hydroxylase:
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EC NUMBERCOMMENTARY
1.14.13.63-

RECOMMENDED NAMEGeneOntology No.
3-hydroxyphenylacetate 6-hydroxylaseGO:0047094

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
3-hydroxyphenylacetate + NAD(P)H + H+ + O2 = 2,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		----

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
oxidation----
reduction----

PATHWAYKEGG LinkMetaCyc Link
No entries in this field

SYSTEMATIC NAMEIUBMB Comments
3-hydroxyphenylacetate,NAD(P)H:oxygen oxidoreductase (6-hydroxylating)3-hydroxyphenylacetate 6-hydroxylase from Flavobacterium sp. is highly specific for 3-hydroxyphenylacetate and uses NADH and NADPH as electron donors with similar efficiency.

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
3,4-dihydroxyphenylacetate 6-hydroxylaseEmericella nidulansQ078T0-673422
3-Hydroxyphenylacetate 6-monooxygenase----
CYP504BEmericella nidulansQ078T0-673422
Oxygenase, 3-hydroxyphenylacetate 6-mono----
m-Hydroxyphenylacetate 6-hydroxylase----
additional informationEmericella nidulansQ078T0the enzyme is a member of a the CYP450 subfamily673422

CAS REGISTRY NUMBERCOMMENTARY
114705-01-0-

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Emericella nidulansstrain BiA1, gene phacB673422Q078T0SwissProtManually annotated by BRENDA team
Emericella nidulans BiA1strain BiA1, gene phacB673422Q078T0SwissProtManually annotated by BRENDA team
Flavobacterium sp.-7426--Manually annotated by BRENDA team
Flavobacterium sp.strain JS-77425--Manually annotated by BRENDA team
Flavobacterium sp. JS-7strain JS-77425--Manually annotated by BRENDA team
Rhodococcus erythropolisstrain S1, highest enzyme activity when grown on 3-hydroxyphenylacetate659614--Manually annotated by BRENDA team
Rhodococcus erythropolis S1strain S1, highest enzyme activity when grown on 3-hydroxyphenylacetate659614--Manually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
2-hydroxyphenoxyacetate + NADH + O2?
show the reaction diagram		Rhodococcus erythropolis-20% of the activity with 3-hydroxyphenylacetate659614--?
2-hydroxyphenylacetate + NAD(P)H + O22,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0low activity673422--?
2-hydroxyphenylacetate + NAD(P)H + O22,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0low activity, step in the 2,5-dihydroxyphenylacetate, i.e.homogentisic acid, catabolic pathway, overview673422--?
3,4-dihydroxyphenylacetate + NAD(P)H + O22,4,5-trihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0-673422--?
3,4-dihydroxyphenylacetate + NAD(P)H + O22,4,5-trihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0step in the 2,5-dihydroxyphenylacetate, i.e.homogentisic acid, catabolic pathway, overview673422the product is a substrate for homogentisate dioxygenase-?
3,4-dihydroxyphenylacetate + NAD(P)H + O2 + H+2,4,5-trihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Flavobacterium sp.--7425-7425-
3,4-Dihydroxyphenylacetate + NADH + O22,4,5-Trihydroxyphenylacetate + NAD+
show the reaction diagram		Flavobacterium sp.--7425-7425-
3-Hydroxyphenylacetate + NAD(P)H + O2?
show the reaction diagram		Flavobacterium sp.-enzyme in the 3-hydroxyphenylacetate catabolism7426---
3-hydroxyphenylacetate + NAD(P)H + O22,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0-673422--?
3-hydroxyphenylacetate + NAD(P)H + O22,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0step in the 2,5-dihydroxyphenylacetate, i.e.homogentisic acid, catabolic pathway, overview673422the product is a substrate for homogentisate dioxygenase-?
3-Hydroxyphenylacetate + NADH + O22,5-Dihydroxyphenylacetate + NAD+
show the reaction diagram		Rhodococcus erythropolis--659614--?
3-Hydroxyphenylacetate + NADH + O22,5-Dihydroxyphenylacetate + NAD+
show the reaction diagram		Flavobacterium sp.-NADPH and NADH are oxidized at a comparable rate7425-7425-
3-Hydroxyphenylacetate + NADH + O22,5-Dihydroxyphenylacetate + NAD+
show the reaction diagram		Rhodococcus erythropolis-enables growth on 3-hydroxyphenylacetate as sole carbon source659614--?
3-Hydroxyphenylacetate + NADPH + O22,5-Dihydroxyphenylacetate + NADP+
show the reaction diagram		Flavobacterium sp.-NADPH and NADH are oxidized at a comparable rate7425-7425-
4-Hydroxyphenylacetate + NADH + O22,4-Dihydroxyphenylacetate + NAD+
show the reaction diagram		Flavobacterium sp.--7425-7425-
additional information?-Flavobacterium sp.-in the absence of oxygen the free enzyme is slowly reduced by NADPH or NADH7425---

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
2-hydroxyphenylacetate + NAD(P)H + O22,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0low activity, step in the 2,5-dihydroxyphenylacetate, i.e.homogentisic acid, catabolic pathway, overview673422--
3,4-dihydroxyphenylacetate + NAD(P)H + O22,4,5-trihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0step in the 2,5-dihydroxyphenylacetate, i.e.homogentisic acid, catabolic pathway, overview673422the product is a substrate for homogentisate dioxygenase-
3-Hydroxyphenylacetate + NAD(P)H + O2?
show the reaction diagram		Flavobacterium sp.-enzyme in the 3-hydroxyphenylacetate catabolism7426--
3-hydroxyphenylacetate + NAD(P)H + O22,5-dihydroxyphenylacetate + NAD(P)+ + H2O
show the reaction diagram		Emericella nidulansQ078T0step in the 2,5-dihydroxyphenylacetate, i.e.homogentisic acid, catabolic pathway, overview673422the product is a substrate for homogentisate dioxygenase-
3-Hydroxyphenylacetate + NADH + O22,5-Dihydroxyphenylacetate + NAD+
show the reaction diagram		Rhodococcus erythropolis-enables growth on 3-hydroxyphenylacetate as sole carbon source659614--

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
FADRhodococcus erythropolis--659614 2D-image
NADHRhodococcus erythropolis--659614 2D-image
NADHEmericella nidulansQ078T0-673422 2D-image
NADPHEmericella nidulansQ078T0-673422 2D-image
FADFlavobacterium sp.-contains 1 mol non-covalently bound FAD per mol of subunit7425 2D-image
additional informationRhodococcus erythropolis-no activity with NADPH659614-

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
Fe2+Emericella nidulansQ078T0the enzyme is a cytochrome P450 monooxygenase containing a heme iron673422

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
2-Chloromercuri-4-nitrophenolFlavobacterium sp.--7425 2D-image
5,5'-dithiobis(2-nitrobenzoate)Flavobacterium sp.--7425 2D-image
Cl-Flavobacterium sp.-competitive to the aromatic substrate7425 2D-image
NEMFlavobacterium sp.--7425 2D-image
p-hydroxymercuribenzoateFlavobacterium sp.--7425 2D-image

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
additional informationEmericella nidulansQ078T0phenylacetate and its hydroxyderivatives strongly induce the enzyme673422-

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
0.09-3,4-DihydroxyphenylacetateFlavobacterium sp.--7425 2D-image
0.079-3-hydroxyphenylacetateFlavobacterium sp.--7425 2D-image
0.15-NADHFlavobacterium sp.--7425 2D-image
0.14-NADPHFlavobacterium sp.--7425 2D-image

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
15.6-3,4-DihydroxyphenylacetateFlavobacterium sp.--7425 2D-image
22.4-3-hydroxyphenylacetateFlavobacterium sp.--7425 2D-image
36-NADHFlavobacterium sp.--7425 2D-image
35.8-NADPHFlavobacterium sp.--7425 2D-image

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
20.1-Flavobacterium sp.--7425
2544-Rhodococcus erythropolis-purified enzyme, pH 8.0, 30°C659614

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
7-Emericella nidulansQ078T0assay at673422
8.38.9Flavobacterium sp.--7425

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
7.38.9Flavobacterium sp.-50% of maximal activity at pH 7.3 and 8.97425

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
37-Emericella nidulansQ078T0assay at673422

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
culture condition:phenylacetic acid-grown cellFlavobacterium sp.--7425Manually annotated by BRENDA team
myceliumEmericella nidulansQ078T0-673422Manually annotated by BRENDA team

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
No entries in this field

PDBSCOPCATHORGANISM
No entries in this field

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
45000-Rhodococcus erythropolis-SDS-PAGE659614
50000-Rhodococcus erythropolis-gel filtration659614
150000200000Flavobacterium sp.-gel filtration7425

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
dimerFlavobacterium sp.-2 * 63000, SDS-PAGE7425
monomerRhodococcus erythropolis-1 * 45000, SDS-PAGE659614

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
6.57Flavobacterium sp.-37°C, stable7425
9-Flavobacterium sp.-strong inactivation above7425

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
No entries in this field

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
3-hydroxyphenylacetate protects against thermal inactivationFlavobacterium sp.-7425

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-70°C, stable for at least 1 monthFlavobacterium sp.-7425

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-Flavobacterium sp.-7425
-Rhodococcus erythropolis-659614

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
DNA and amino acid sequence determination and analysis, expression pattern, sequence comparison, expression in a recombinant Aspergillus nidulans strainEmericella nidulansQ078T0673422

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
additional informationEmericella nidulansQ078T0a phacB-disrupted strain DELTAphacB does not grow on 3-hydroxy-, 4-hydroxy-, or 3,4-dihydroxy-phenylacetate, overview673422

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
7425van Berkel, W.J.H.; van den Tweel, W.J.J.Purification and characterisation of 3-hydroxyphenylacetate 6-hydroxylase: a novel FAD-dependent monooxygenase from a Flavobacterium speciesEur. J. Biochem.201585-5911991Flavobacterium sp. PubMed
7426Van den Tweel, W.J.J.; Smits, J.P.; de Bont, J.A.M.Catabolism of DL-alpha-phenylhydracrylic, phenylacetic and 3- and 4-hydroxyphenylacetic acid via homogentisic acid in a Flavobacterium sp.Arch. Microbiol.149207-2131988Flavobacterium sp.-
659614Suemori, A.; Nakajima, K.; Kurane, R.; Nakamura, Y.Purification and characterization of o-hydroxyphenylacetate 5-hydroxylase, m-hydroxyphenylacetate 6-hydroxylase and p-hydroxyphenylacetate 1-hydroxylase from Rhodococcus erythropolisJ. Ferment. Bioeng.81133-1371996Rhodococcus erythropolis-
673422Ferrer-Sevillano, F.; Fernandez-Canon, J.M.Novel phacB-encoded cytochrome P450 monooxygenase from Aspergillus nidulans with 3-hydroxyphenylacetate 6-hydroxylase and 3,4-dihydroxyphenylacetate 6-hydroxylase activitiesEukaryot. Cell6514-5202007Emericella nidulans PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.63)
ExplorEnz
ExPASy
KEGG
MetaCyc
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)