DB code: M00004

CATH domain 3.30.43.10 : Uridine Diphospho-n-acetylenolpyruvylglucosamine Reductase; domain 2 Catalytic domain
3.30.465.20 : Uridine Diphospho-n-acetylenolpyruvylglucosamine Reductase; domain 3 Catalytic domain
3.40.462.10 : Vanillyl-alcohol Oxidase; Chain A, domain 3 Catalytic domain
1.10.45.10 : Vanillyl-alcohol Oxidase; Chain A, domain 4
E.C. 1.1.3.38
CSA 1vao
M-CSA 1vao
MACiE M0103

CATH domain Related DB codes (homologues)
1.10.45.10 : Vanillyl-alcohol Oxidase; Chain A, domain 4 M00179
3.30.43.10 : Uridine Diphospho-n-acetylenolpyruvylglucosamine Reductase; domain 2 M00001 M00039 M00179 T00003
3.30.465.20 : Uridine Diphospho-n-acetylenolpyruvylglucosamine Reductase; domain 3 M00001 M00179
3.40.462.10 : Vanillyl-alcohol Oxidase; Chain A, domain 3 M00179

Uniprot Enzyme Name
UniprotKB Protein name Synonyms Pfam
P56216 Vanillyl-alcohol oxidase
EC 1.1.3.38
Aryl-alcohol oxidase
4-allylphenol oxidase
PF02913 (FAD-oxidase_C)
PF01565 (FAD_binding_4)
[Graphical View]

KEGG enzyme name
vanillyl-alcohol oxidase
4-hydroxy-2-methoxybenzyl alcohol oxidase

UniprotKB: Accession Number Entry name Activity Subunit Subcellular location Cofactor
P56216 VAOX_PENSI Vanillyl alcohol + O(2) = vanillin + H(2)O(2). Homooctamer (tetramer of tightly interacting dimers). Peroxisome. Cytoplasm. Binds 1 FAD covalently per subunit.

KEGG Pathways
Map code Pathways E.C.
MAP00623 2,4-Dichlorobenzoate degradation

Compound table
Cofactors Substrates Products Intermediates
KEGG-id C00016 C06317 C00007 C00755 C00027
E.C.
Compound FAD Vanillyl alcohol O2 Vanillin H2O2 p-quinone methide intermediate
Type amide group,amine group,aromatic ring (only carbon atom),aromatic ring (with nitrogen atoms),carbohydrate,nucleotide aromatic ring (only carbon atom),carbohydrate others aromatic ring (only carbon atom),carbohydrate others
ChEBI 16238
16238
18353
18353
15379
26689
27140
15379
26689
27140
18346
18346
16240
16240
PubChem 643975
643975
62348
62348
977
977
1183
1183
22326046
784
22326046
784
1ahuA01 Analogue:FAA Unbound Unbound Unbound Unbound Unbound
1ahuB01 Analogue:FAA Unbound Unbound Unbound Unbound Unbound
1ahvA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1ahvB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1ahzA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1ahzB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1dznA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1dznB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1e0yA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1e0yB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1e8fA01 Unbound Unbound Unbound Unbound Unbound Unbound
1e8fB01 Unbound Unbound Unbound Unbound Unbound Unbound
1e8gA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1e8gB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1e8hA01 Analogue:ADP Unbound Unbound Unbound Unbound Unbound
1e8hB01 Analogue:ADP Unbound Unbound Unbound Unbound Unbound
1qltA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1qltB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1qluA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1qluB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1vaoA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1vaoB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1w1jA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1w1jB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1w1kA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1w1kB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1w1lA01 Analogue:EUG-FAD Unbound Unbound Unbound Unbound Unbound
1w1lB01 Analogue:EUG-FAD Unbound Unbound Unbound Unbound Unbound
1w1mA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1w1mB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
2vaoA01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
2vaoB01 Bound:FAD Unbound Unbound Unbound Unbound Unbound
1ahuA02 Unbound Unbound Unbound Unbound Unbound Unbound
1ahuB02 Unbound Unbound Unbound Unbound Unbound Unbound
1ahvA02 Unbound Unbound Unbound Unbound Unbound Unbound
1ahvB02 Unbound Unbound Unbound Unbound Unbound Unbound
1ahzA02 Unbound Unbound Unbound Unbound Unbound Unbound
1ahzB02 Unbound Unbound Unbound Unbound Unbound Unbound
1dznA02 Unbound Unbound Unbound Unbound Unbound Unbound
1dznB02 Unbound Unbound Unbound Unbound Unbound Unbound
1e0yA02 Unbound Unbound Unbound Unbound Unbound Unbound
1e0yB02 Unbound Unbound Unbound Unbound Unbound Unbound
1e8fA02 Unbound Unbound Unbound Unbound Unbound Unbound
1e8fB02 Unbound Unbound Unbound Unbound Unbound Unbound
1e8gA02 Unbound Unbound Unbound Unbound Unbound Unbound
1e8gB02 Unbound Unbound Unbound Unbound Unbound Unbound
1e8hA02 Unbound Unbound Unbound Unbound Unbound Unbound
1e8hB02 Unbound Unbound Unbound Unbound Unbound Unbound
1qltA02 Unbound Unbound Unbound Unbound Unbound Unbound
1qltB02 Unbound Unbound Unbound Unbound Unbound Unbound
1qluA02 Unbound Unbound Unbound Unbound Unbound Unbound
1qluB02 Unbound Unbound Unbound Unbound Unbound Unbound
1vaoA02 Unbound Unbound Unbound Unbound Unbound Unbound
1vaoB02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1jA02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1jB02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1kA02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1kB02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1lA02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1lB02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1mA02 Unbound Unbound Unbound Unbound Unbound Unbound
1w1mB02 Unbound Unbound Unbound Unbound Unbound Unbound
2vaoA02 Unbound Unbound Unbound Unbound Unbound Unbound
2vaoB02 Unbound Unbound Unbound Unbound Unbound Unbound
1ahuA03 Unbound Analogue:FAA Unbound Unbound Unbound Unbound
1ahuB03 Unbound Analogue:FAA Unbound Unbound Unbound Unbound
1ahvA03 Unbound Analogue:NCR Unbound Unbound Unbound Unbound
1ahvB03 Unbound Analogue:NCR Unbound Unbound Unbound Unbound
1ahzA03 Unbound Analogue:EPT Unbound Unbound Unbound Unbound
1ahzB03 Unbound Unbound Unbound Unbound Unbound Unbound
1dznA03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1dznB03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1e0yA03 Unbound Unbound Unbound Unbound Unbound Unbound
1e0yB03 Unbound Analogue:FCR Unbound Unbound Unbound Unbound
1e8fA03 Unbound Unbound Unbound Unbound Unbound Unbound
1e8fB03 Unbound Unbound Unbound Unbound Unbound Unbound
1e8gA03 Unbound Analogue:FCR Unbound Unbound Unbound Unbound
1e8gB03 Unbound Analogue:FCR Unbound Unbound Unbound Unbound
1e8hA03 Unbound Unbound Unbound Unbound Unbound Unbound
1e8hB03 Unbound Unbound Unbound Unbound Unbound Unbound
1qltA03 Unbound Unbound Unbound Unbound Unbound Unbound
1qltB03 Unbound Unbound Unbound Unbound Unbound Unbound
1qluA03 Unbound Analogue:EUG Unbound Analogue:EUG Unbound Unbound
1qluB03 Unbound Analogue:EUG Unbound Analogue:EUG Unbound Unbound
1vaoA03 Unbound Unbound Unbound Unbound Unbound Unbound
1vaoB03 Unbound Unbound Unbound Unbound Unbound Unbound
1w1jA03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1jB03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1kA03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1kB03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1lA03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1lB03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1mA03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1w1mB03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
2vaoA03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
2vaoB03 Unbound Unbound Unbound Analogue:EUG Unbound Unbound
1ahuA04 Unbound Unbound Unbound Unbound Unbound Unbound
1ahuB04 Unbound Unbound Unbound Unbound Unbound Unbound
1ahvA04 Unbound Unbound Unbound Unbound Unbound Unbound
1ahvB04 Unbound Unbound Unbound Unbound Unbound Unbound
1ahzA04 Unbound Unbound Unbound Unbound Unbound Unbound
1ahzB04 Unbound Unbound Unbound Unbound Unbound Unbound
1dznA04 Unbound Unbound Unbound Unbound Unbound Unbound
1dznB04 Unbound Unbound Unbound Unbound Unbound Unbound
1e0yA04 Unbound Unbound Unbound Unbound Unbound Unbound
1e0yB04 Unbound Unbound Unbound Unbound Unbound Unbound
1e8fA04 Unbound Unbound Unbound Unbound Unbound Unbound
1e8fB04 Unbound Unbound Unbound Unbound Unbound Unbound
1e8gA04 Unbound Unbound Unbound Unbound Unbound Unbound
1e8gB04 Unbound Unbound Unbound Unbound Unbound Unbound
1e8hA04 Unbound Unbound Unbound Unbound Unbound Unbound
1e8hB04 Unbound Unbound Unbound Unbound Unbound Unbound
1qltA04 Unbound Unbound Unbound Unbound Unbound Unbound
1qltB04 Unbound Unbound Unbound Unbound Unbound Unbound
1qluA04 Unbound Unbound Unbound Unbound Unbound Unbound
1qluB04 Unbound Unbound Unbound Unbound Unbound Unbound
1vaoA04 Unbound Unbound Unbound Unbound Unbound Unbound
1vaoB04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1jA04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1jB04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1kA04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1kB04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1lA04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1lB04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1mA04 Unbound Unbound Unbound Unbound Unbound Unbound
1w1mB04 Unbound Unbound Unbound Unbound Unbound Unbound
2vaoA04 Unbound Unbound Unbound Unbound Unbound Unbound
2vaoB04 Unbound Unbound Unbound Unbound Unbound Unbound

Reference for Active-site residues
resource references E.C.
Swiss-prot;P56216 & literature [10]

Active-site residues
PDB Catalytic residues Cofactor-binding residues Modified residues Main-chain involved in catalysis Comment
1ahuA01 TYR 108
1ahuB01 TYR 108
1ahvA01 TYR 108
1ahvB01 TYR 108
1ahzA01 TYR 108
1ahzB01 TYR 108
1dznA01 TYR 108
1dznB01 TYR 108
1e0yA01 TYR 108
1e0yB01 TYR 108
1e8fA01 TYR 108 mutant H61T
1e8fB01 TYR 108 mutant H61T
1e8gA01 TYR 108 mutant H61T
1e8gB01 TYR 108 mutant H61T
1e8hA01 TYR 108 mutant H61T
1e8hB01 TYR 108 mutant H61T
1qltA01 TYR 108
1qltB01 TYR 108
1qluA01 TYR 108
1qluB01 TYR 108
1vaoA01 TYR 108
1vaoB01 TYR 108
1w1jA01 TYR 108
1w1jB01 TYR 108
1w1kA01 TYR 108
1w1kB01 TYR 108
1w1lA01 TYR 108
1w1lB01 TYR 108
1w1mA01 TYR 108
1w1mB01 TYR 108
2vaoA01 TYR 108
2vaoB01 TYR 108
1ahuA02 ASP 170
1ahuB02 ASP 170
1ahvA02 ASP 170
1ahvB02 ASP 170
1ahzA02 ASP 170
1ahzB02 ASP 170
1dznA02 mutant D170S
1dznB02 mutant D170S
1e0yA02 mutant D170S
1e0yB02 mutant D170S
1e8fA02 ASP 170
1e8fB02 ASP 170
1e8gA02 ASP 170
1e8gB02 ASP 170
1e8hA02 ASP 170
1e8hB02 ASP 170
1qltA02 ASP 170
1qltB02 ASP 170
1qluA02 ASP 170
1qluB02 ASP 170
1vaoA02 ASP 170
1vaoB02 ASP 170
1w1jA02 ASP 170
1w1jB02 ASP 170
1w1kA02 ASP 170 mutant I238T
1w1kB02 ASP 170 mutant I238T
1w1lA02 ASP 170
1w1lB02 ASP 170
1w1mA02 ASP 170
1w1mB02 ASP 170
2vaoA02 ASP 170
2vaoB02 ASP 170
1ahuA03 TYR 503;ARG 504 HIS 422(FAD binding)
1ahuB03 TYR 503;ARG 504 HIS 422(FAD binding)
1ahvA03 TYR 503;ARG 504 HIS 422(FAD binding)
1ahvB03 TYR 503;ARG 504 HIS 422(FAD binding)
1ahzA03 TYR 503;ARG 504 HIS 422(FAD binding)
1ahzB03 TYR 503;ARG 504 HIS 422(FAD binding)
1dznA03 TYR 503;ARG 504 HIS 422(FAD binding)
1dznB03 TYR 503;ARG 504 HIS 422(FAD binding)
1e0yA03 TYR 503;ARG 504 HIS 422(FAD binding) mutant T457E
1e0yB03 TYR 503;ARG 504 HIS 422(FAD binding) mutant T457E
1e8fA03 TYR 503;ARG 504 HIS 422(FAD binding)
1e8fB03 TYR 503;ARG 504 HIS 422(FAD binding)
1e8gA03 TYR 503;ARG 504 HIS 422(FAD binding)
1e8gB03 TYR 503;ARG 504 HIS 422(FAD binding)
1e8hA03 TYR 503;ARG 504 HIS 422(FAD binding)
1e8hB03 TYR 503;ARG 504 HIS 422(FAD binding)
1qltA03 TYR 503;ARG 504 mutant H422A
1qltB03 TYR 503;ARG 504 mutant H422A
1qluA03 TYR 503;ARG 504 mutant H422A
1qluB03 TYR 503;ARG 504 mutant H422A
1vaoA03 TYR 503;ARG 504 HIS 422(FAD binding)
1vaoB03 TYR 503;ARG 504 HIS 422(FAD binding)
1w1jA03 TYR 503;ARG 504 HIS 422(FAD binding) mutant T505S
1w1jB03 TYR 503;ARG 504 HIS 422(FAD binding) mutant T505S
1w1kA03 TYR 503;ARG 504 HIS 422(FAD binding)
1w1kB03 TYR 503;ARG 504 HIS 422(FAD binding)
1w1lA03 TYR 503;ARG 504 HIS 422(FAD binding) mutant F454Y
1w1lB03 TYR 503;ARG 504 HIS 422(FAD binding) mutant F454Y
1w1mA03 TYR 503;ARG 504 HIS 422(FAD binding) mutant E502G
1w1mB03 TYR 503;ARG 504 HIS 422(FAD binding) mutant E502G
2vaoA03 TYR 503;ARG 504 HIS 422(FAD binding)
2vaoB03 TYR 503;ARG 504 HIS 422(FAD binding)
1ahuA04
1ahuB04
1ahvA04
1ahvB04
1ahzA04
1ahzB04
1dznA04
1dznB04
1e0yA04
1e0yB04
1e8fA04
1e8fB04
1e8gA04
1e8gB04
1e8hA04
1e8hB04
1qltA04
1qltB04
1qluA04
1qluB04
1vaoA04
1vaoB04
1w1jA04
1w1jB04
1w1kA04
1w1kB04
1w1lA04
1w1lB04
1w1mA04
1w1mB04
2vaoA04
2vaoB04

References for Catalytic Mechanism
References Sections No. of steps in catalysis
[2]
p.276-277
[4]
Equation 4, Scheme 1, p.18115-18116
[6]
Fig.10, p.915-917
[7]
Scheme 1, p.35518-35520
[8]
Scheme 1, Fig.3, p.109
[10]
Fig.1, Fig.8, p.14806-14807
[11]
Scheme 1, Fig.5, p.9454-9456
[13]
Fig.1
[16]
Fig.2, p.182-186
[17]
Fig.1, p.33498-33499

References
[1]
Resource
Comments CHARACTERIZATION
Medline ID 93011092
PubMed ID 1396672
Journal Eur J Biochem
Year 1992
Volume 208
Pages 651-7
Authors de Jong E, van Berkel WJ, van der Zwan RP, de Bont JA
Title Purification and characterization of vanillyl-alcohol oxidase from Penicillium simplicissimum. A novel aromatic alcohol oxidase containing covalently bound FAD.
Related PDB
Related UniProtKB P56216
[2]
Resource
Comments SUBSTRATE SPECIFICITY
Medline ID 96096749
PubMed ID 8529652
Journal Eur J Biochem
Year 1995
Volume 234
Pages 271-7
Authors Fraaije MW, Veeger C, van Berkel WJ
Title Substrate specificity of flavin-dependent vanillyl-alcohol oxidase from Penicillium simplicissimum. Evidence for the production of 4-hydroxycinnamyl alcohols from 4-allylphenols.
Related PDB
Related UniProtKB P56216
[3]
Resource
Comments
Medline ID
PubMed ID 9013853
Journal FEBS Lett
Year 1997
Volume 402
Pages 33-5
Authors Fraaije MW, Mattevi A, van Berkel WJ
Title Mercuration of vanillyl-alcohol oxidase from Penicillium simplicissimum generates inactive dimers.
Related PDB
Related UniProtKB
[4]
Resource
Comments
Medline ID
PubMed ID 9218444
Journal J Biol Chem
Year 1997
Volume 272
Pages 18111-6
Authors Fraaije MW, van Berkel WJ
Title Catalytic mechanism of the oxidative demethylation of 4-(methoxymethyl)phenol by vanillyl-alcohol oxidase. Evidence for formation of a p-quinone methide intermediate.
Related PDB
Related UniProtKB
[5]
Resource
Comments X-RAY CRYSTALLOGRAPHY (2.5 AND 3.2 ANGSTROMS)
Medline ID 97285922
PubMed ID 9141139
Journal Proteins
Year 1997
Volume 27
Pages 601-3
Authors Mattevi A, Fraaije MW, Coda A, van Berkel WJ
Title Crystallization and preliminary X-ray analysis of the flavoenzyme vanillyl-alcohol oxidase from Penicillium simplicissimum.
Related PDB 1ahu 1ahv 1ahz 1vao 2vao
Related UniProtKB P56216
[6]
Resource
Comments
Medline ID
PubMed ID 9261083
Journal Structure
Year 1997
Volume 5
Pages 907-20
Authors Mattevi A, Fraaije MW, Mozzarelli A, Olivi L, Coda A, van Berkel WJ
Title Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrate specificity.
Related PDB
Related UniProtKB
[7]
Resource
Comments X-RAY CRYSTALLOGRAPHY OF MUTANTS (2.2 ANGSTROMS)
Medline ID 20054426
PubMed ID 10585424
Journal J Biol Chem
Year 1999
Volume 274
Pages 35514-20
Authors Fraaije MW, van den Heuvel RH, van Berkel WJ, Mattevi A
Title Covalent flavinylation is essential for efficient redox catalysis in vanillyl-alcohol oxidase.
Related PDB 1qlt 1qlu
Related UniProtKB P56216
[8]
Resource
Comments
Medline ID
PubMed ID 10996306
Journal FEBS Lett
Year 2000
Volume 481
Pages 109-12
Authors van den Heuvel RH, Fraaije MW, van Berkel WJ
Title Direction of the reactivity of vanillyl-alcohol oxidase with 4-alkylphenols.
Related PDB
Related UniProtKB
[9]
Resource
Comments X-RAY CRYSTALLOGRAPHY OF MUTANTS (2.1 ANGSTROMS)
Medline ID 20556311
PubMed ID 10984479
Journal J Biol Chem
Year 2000
Volume 275
Pages 38654-8
Authors Fraaije MW, van Den Heuvel RH, van Berkel WJ, Mattevi A
Title Structural analysis of flavinylation in vanillyl-alcohol oxidase.
Related PDB 1e8f 1e8g 1e8h
Related UniProtKB P56216
[10]
Resource
Comments X-RAY CRYSTALLOGRAPHY OF D170S MUTANT (2.8 ANGSTROMS)
Medline ID 20270176
PubMed ID 10809721
Journal J Biol Chem
Year 2000
Volume 275
Pages 14799-808
Authors van den Heuvel RH, Fraaije MW, Mattevi A, van Berkel WJ
Title Asp-170 is crucial for the redox properties of vanillyl-alcohol oxidase.
Related PDB 1dzn
Related UniProtKB P56216
[11]
Resource
Comments X-RAY CRYSTALLOGRAPHY OF D170S/T457E MUTANT (2.75 ANGSTROMS)
Medline ID 20402555
PubMed ID 10920192
Journal Proc Natl Acad Sci U S A
Year 2000
Volume 97
Pages 9455-60
Authors van Den Heuvel RH, Fraaije MW, Ferrer M, Mattevi A, van Berkel WJ
Title Inversion of stereospecificity of vanillyl-alcohol oxidase.
Related PDB 1e0y
Related UniProtKB P56216
[12]
Resource
Comments
Medline ID
PubMed ID 10752605
Journal Protein Sci
Year 2000
Volume 9
Pages 435-9
Authors van Berkel WJ, van den Heuvel RH, Versluis C, Heck AJ
Title Detection of intact megaDalton protein assemblies of vanillyl-alcohol oxidase by mass spectrometry.
Related PDB
Related UniProtKB
[13]
Resource
Comments
Medline ID
PubMed ID 10694883
Journal Trends Biochem Sci
Year 2000
Volume 25
Pages 126-32
Authors Fraaije MW, Mattevi A
Title Flavoenzymes: diverse catalysts with recurrent features.
Related PDB
Related UniProtKB
[14]
Resource
Comments
Medline ID
PubMed ID 11513884
Journal FEBS Lett
Year 2001
Volume 503
Pages 213-6
Authors van den Heuvel RH, Partridge J, Laane C, Halling PJ, van Berkel WJ
Title Tuning of the product spectrum of vanillyl-alcohol oxidase by medium engineering.
Related PDB
Related UniProtKB
[15]
Resource
Comments
Medline ID
PubMed ID 12107187
Journal J Biol Chem
Year 2002
Volume 277
Pages 36425-32
Authors Tahallah N, Van Den Heuvel RH, Van Den Berg WA, Maier CS, Van Berkel WJ, Heck AJ
Title Cofactor-dependent assembly of the flavoenzyme vanillyl-alcohol oxidase.
Related PDB
Related UniProtKB
[16]
Resource
Comments
Medline ID
PubMed ID 12078493
Journal Methods Enzymol
Year 2002
Volume 353
Pages 177-86
Authors van den Heuvel RH, Fraaije MW, van Berkel WJ
Title Redox properties of vanillyl-alcohol oxidase.
Related PDB
Related UniProtKB
[17]
Resource
Comments X-ray crystallography
Medline ID
PubMed ID 15169773
Journal J Biol Chem
Year 2004
Volume 279
Pages 33492-500
Authors van den Heuvel RH, van den Berg WA, Rovida S, van Berkel WJ
Title Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.
Related PDB 1w1j 1w1k 1w1l 1w1m
Related UniProtKB

Comments
Although vanillyl alcohol (C06317) is annotated as a substrate, 4-(methoxymethyl)phenol seems to be a major substrate, according to the literature. This enzyme seems to catalyze oxidative demethylation of 4-(methoxymethyl)phenol.
According to the literature [10], this enzyme catalyzes the following reactions:
(A) Hydride transfer from methyl group of substrate to FAD, forming p-quinone methide intermediate and FADH2:
(B) Hydride transfer from FADH2 to O2 (Re-oxidation of FAD by O2, releasing H2O2):
(C) Additive double-bond deformation; Addition of H2O to p-quinone methide intermediate (Hydroxylation):
(D) Eliminative double-bond formation; Elimination of H2O (or Elimination of methanol in the case of 4-(methoxymethyl)phenol as a substrate):

Created Updated
2005-06-01 2009-02-26