KEGG   ENZYME: 1.14.13.156Help
Entry
EC 1.14.13.156              Enzyme                                 

Name
1,8-cineole 2-endo-monooxygenase;
P450cin;
CYP176A;
CYP176A1
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
1,8-cineole,NADPH:oxygen oxidoreductase (2-endo-hydroxylating)
Reaction(IUBMB)
1,8-cineole + NADPH + H+ + O2 = 2-endo-hydroxy-1,8-cineole + NADP+ + H2O [RN:R08784]
Reaction(KEGG)
Substrate
1,8-cineole [CPD:C09844];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
2-endo-hydroxy-1,8-cineole [CPD:C03092];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
A heme-thiolate protein (P-450) which uses a flavodoxin-like redox partner to reduce the heme iron. Isolated from the bacterium Citrobacter braakii, which can use 1,8-cineole as the sole source of carbon.
History
EC 1.14.13.156 created 2012
Pathway
Monoterpenoid biosynthesis
Reference
1  [PMID:12016226]
  Authors
Hawkes DB, Adams GW, Burlingame AL, Ortiz de Montellano PR, De Voss JJ
  Title
Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization.
  Journal
J. Biol. Chem. 277 (2002) 27725-32.
  Sequence
[up:Q8VQF6]
Reference
2  [PMID:15260491]
  Authors
Meharenna YT, Li H, Hawkes DB, Pearson AG, De Voss J, Poulos TL
  Title
Crystal structure of P450cin in a complex with its substrate, 1,8-cineole, a close structural homologue to D-camphor, the substrate for P450cam.
  Journal
Biochemistry. 43 (2004) 9487-94.
  Sequence
[up:Q8VQF6]
Reference
3  [PMID:17606612]
  Authors
Kimmich N, Das A, Sevrioukova I, Meharenna Y, Sligar SG, Poulos TL
  Title
Electron transfer between cytochrome P450cin and its FMN-containing redox partner, cindoxin.
  Journal
J. Biol. Chem. 282 (2007) 27006-11.
  Sequence
[up:Q8VQF6]
Reference
4  [PMID:18270198]
  Authors
Meharenna YT, Slessor KE, Cavaignac SM, Poulos TL, De Voss JJ
  Title
The critical role of substrate-protein hydrogen bonding in the control of regioselective hydroxylation in p450cin.
  Journal
J. Biol. Chem. 283 (2008) 10804-12.
  Sequence
[up:Q8VQF6]
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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