KEGG   ENZYME: 1.14.13.69Help
Entry
EC 1.14.13.69               Enzyme                                 

Name
alkene monooxygenase;
alkene epoxygenase;
etnABCD (gene names);
amoABCDE (gene names)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
alkene,NADH:oxygen oxidoreductase
Reaction(IUBMB)
propene + NADH + H+ + O2 = 1,2-epoxypropane + NAD+ + H2O [RN:R07194]
Reaction(KEGG)
Substrate
propene [CPD:C11505];
NADH [CPD:C00004];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
1,2-epoxypropane [CPD:C15508];
NAD+ [CPD:C00003];
H2O [CPD:C00001]
Comment
This bacterial binuclear non-heme iron enzyme is a multicomponent enzyme complex comprising an oxygenase, a reductase, and a Rieske-type ferredoxin. The enzyme from the bacterium Xanthobacter sp. strain Py2 contains an additional small protein of unknown function that is essential for activity. In general, the enzyme oxygenates C2 to C6 aliphatic alkenes, although enzymes from different organisms show different substrate range. With propene as substrate, the stereospecificity of the epoxypropane formed is 95% (R) and 5% (S).
History
EC 1.14.13.69 created 2001
Pathway
ec00625  Chloroalkane and chloroalkene degradation
ec01100  Metabolic pathways
ec01120  Microbial metabolism in diverse environments
Orthology
K22353  alkene monooxygenase alpha subunit
K22354  alkene monooxygenase beta subunit
K22357  alkene monooxygenase alpha subunit
K22358  alkene monooxygenase beta subunit
K22359  alkene monooxygenase gamma subunit
Genes
XAU: Xaut_4857 Xaut_4858 Xaut_4861
MSA: Mycsm_01889 Mycsm_01891
MCB: Mycch_5977 Mycch_5979
MRH: MycrhN_2951 MycrhN_2953
NCA: Noca_4807 Noca_4809
Taxonomy
Reference
1  [PMID:9312093]
  Authors
Small FJ, Ensign SA.
  Title
Alkene monooxygenase from Xanthobacter strain Py2. Purification and characterization of a four-component system central to the bacterial metabolism of aliphatic alkenes.
  Journal
J Biol Chem 272:24913-20 (1997)
DOI:10.1074/jbc.272.40.24913
Reference
2  [PMID:9266707]
  Authors
Gallagher SC, Cammack R, Dalton H.
  Title
Alkene monooxygenase from Nocardia corallina B-276 is a member of the class of dinuclear iron proteins capable of stereospecific epoxygenation reactions.
  Journal
Eur J Biochem 247:635-41 (1997)
DOI:10.1111/j.1432-1033.1997.00635.x
Reference
3  [PMID:10103255]
  Authors
Zhou NY, Jenkins A, Chan Kwo Chion CK, Leak DJ.
  Title
The alkene monooxygenase from Xanthobacter strain Py2 is closely related to aromatic monooxygenases and catalyzes aromatic monohydroxylation of benzene, toluene, and phenol.
  Journal
Appl Environ Microbiol 65:1589-95 (1999)
  Sequence
Reference
4  [PMID:15476981]
  Authors
Champreda V, Zhou NY, Leak DJ
  Title
Heterologous expression of alkene monooxygenase components from Xanthobacter autotrophicus Py2 and reconstitution of the active complex.
  Journal
FEMS Microbiol Lett 239:309-18 (2004)
DOI:10.1016/j.femsle.2004.09.002
Reference
5  [PMID:16402171]
  Authors
Champreda V, Choi YJ, Zhou NY, Leak DJ
  Title
Alteration of the stereo- and regioselectivity of alkene monooxygenase based on coupling protein interactions.
  Journal
Appl Microbiol Biotechnol 71:840-7 (2006)
DOI:10.1007/s00253-005-0208-2
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.69
IUBMB Enzyme Nomenclature: 1.14.13.69
ExPASy - ENZYME nomenclature database: 1.14.13.69
UM-BBD (Biocatalysis/Biodegradation Database): 1.14.13.69
BRENDA, the Enzyme Database: 1.14.13.69
CAS: 63439-50-9

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