KEGG   ORTHOLOGY: K10566
Entry
K10566            Tight     KO                                     

Name
oxdB
Definition
phenylacetaldoxime dehydratase [EC:4.99.1.7]
Pathway
ko00460  Cyanoamino acid metabolism
ko00643  Styrene degradation
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko01120  Microbial metabolism in diverse environments
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K10566  oxdB; phenylacetaldoxime dehydratase
  09111 Xenobiotics biodegradation and metabolism
   00643 Styrene degradation
    K10566  oxdB; phenylacetaldoxime dehydratase
Enzymes [BR:ko01000]
 4. Lyases
  4.99  Other lyases
   4.99.1  Sole sub-subclass for lyases that do not belong in the other subclasses
    4.99.1.7  phenylacetaldoxime dehydratase
     K10566  oxdB; phenylacetaldoxime dehydratase
Other DBs
RN: R07638
GO: 0018814
Genes
BACO: OXB_1097
Reference
  Authors
Kato Y, Nakamura K, Sakiyama H, Mayhew SG, Asano Y
  Title
Novel heme-containing lyase, phenylacetaldoxime dehydratase from Bacillus sp. strain OxB-1: purification, characterization, and molecular cloning of the gene.
  Journal
Biochemistry 39:800-9 (2000)
DOI:10.1021/bi991598u
  Sequence
[baco:OXB_1097]

KEGG   ENZYME: 4.99.1.7
Entry
EC 4.99.1.7                 Enzyme                                 

Name
phenylacetaldoxime dehydratase;
PAOx dehydratase;
arylacetaldoxime dehydratase;
OxdB;
(Z)-phenylacetaldehyde-oxime hydro-lyase
Class
Lyases;
Other lyases;
Sole sub-subclass for lyases that do not belong in the other subclasses
Sysname
(Z)-phenylacetaldehyde-oxime hydro-lyase (phenylacetonitrile-forming)
Reaction(IUBMB)
(Z)-phenylacetaldehyde oxime = phenylacetonitrile + H2O [RN:R07638]
Reaction(KEGG)
R07638
Substrate
(Z)-phenylacetaldehyde oxime [CPD:C16075]
Product
phenylacetonitrile [CPD:C16074];
H2O [CPD:C00001]
Comment
The enzyme from Bacillus sp. OxB-1 contains protoheme IX, the iron of which must be in the form iron(II) for activity. (Z)-Phenylacetaldoxime binds to ferric heme (the iron(III) form) via the oxygen atom whereas it binds to the active ferrous form via the nitrogen atom. In this way, the oxidation state of the heme controls the coordination stucture of the substrate---heme complex, which regulates enzyme activity [2]. The enzyme is active towards several (Z)-arylacetaldoximes and (E/Z)-alkylaldoximes as well as towards arylalkylaldoximes such as 3-phenylpropionaldoxime and 4-phenylbutyraldoxime. However, it is inactive with phenylacetaldoximes that have a substituent group at an alpha-site of an oxime group, for example, with (E/Z)-2-phenylpropionaldoxime and (E/Z)-mandelaldoxime. The activity of the enzyme is inhibited completely by the heavy-metal cations Cu+, Cu2+, Ag+ and Hg+ whereas Fe2+ and Sn2+ have an activatory effect.
History
EC 4.99.1.7 created 2005
Pathway
ec00460  Cyanoamino acid metabolism
ec00643  Styrene degradation
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
ec01120  Microbial metabolism in diverse environments
Orthology
K10566  phenylacetaldoxime dehydratase
Genes
BACO: OXB_1097
Reference
1  [PMID:10651646]
  Authors
Kato Y, Nakamura K, Sakiyama H, Mayhew SG, Asano Y.
  Title
Novel heme-containing lyase, phenylacetaldoxime dehydratase from Bacillus sp. strain OxB-1: purification, characterization, and molecular cloning of the gene.
  Journal
Biochemistry 39:800-9 (2000)
DOI:10.1021/bi991598u
  Sequence
[baco:OXB_1097]
Reference
2  [PMID:15596434]
  Authors
Kobayashi K, Yoshioka S, Kato Y, Asano Y, Aono S.
  Title
Regulation of aldoxime dehydratase activity by redox-dependent change in the coordination structure of the aldoxime-heme complex.
  Journal
J Biol Chem 280:5486-90 (2005)
DOI:10.1074/jbc.M410474200
Other DBs
ExplorEnz - The Enzyme Database: 4.99.1.7
IUBMB Enzyme Nomenclature: 4.99.1.7
ExPASy - ENZYME nomenclature database: 4.99.1.7
UM-BBD (Biocatalysis/Biodegradation Database): 4.99.1.7
BRENDA, the Enzyme Database: 4.99.1.7
CAS: 203210-76-8

KEGG   REACTION: R07638
Entry
R07638                      Reaction                               

Name
(Z)-phenylacetaldehyde-oxime hydro-lyase
Definition
(Z)-Phenylacetaldehyde oxime <=> Phenylacetonitrile + H2O
Equation
Comment
the second step of three-step reaction (see R11732, R10041+R07638+R11733)
Reaction class
RC01076  C16074_C16075
Enzyme
1.14.14.44      4.99.1.7
Pathway
rn00460  Cyanoamino acid metabolism
rn00643  Styrene degradation
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
rn01120  Microbial metabolism in diverse environments
Orthology
K00495  phenylacetaldehyde oxime monooxygenase [EC:1.14.14.44]
K10566  phenylacetaldoxime dehydratase [EC:4.99.1.7]
Other DBs
RHEA: 20072

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