KEGG   ENZYME: 1.14.14.53Help
Entry
EC 1.14.14.53               Enzyme                                 

Name
(R)-limonene 6-monooxygenase;
(+)-limonene-6-hydroxylase;
(+)-limonene 6-monooxygenase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
(R)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
(R)-limonene + [reduced NADPH---hemoprotein reductase] + O2 = (+)-trans-carveol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R06119]
Reaction(KEGG)
Substrate
(R)-limonene;
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(+)-trans-carveol [CPD:C11409];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
The reaction is stereospecific with over 95% yield of (+)-trans-carveol from (R)-limonene. (S)-Limonene, the substrate for EC 1.14.14.51, (S)-limonene 6-monooxygenase, is not a substrate. Forms part of the carvone biosynthesis pathway in Carum carvi (caraway) seeds.
History
EC 1.14.14.53 created 2003 as EC 1.14.13.80, transferred 2017 to EC 1.14.14.53
Pathway
ec00902  Monoterpenoid biosynthesis
ec00903  Limonene and pinene degradation
ec01110  Biosynthesis of secondary metabolites
Orthology
K17719  cytochrome P450 family 2 subfamily C polypeptide 9
K17721  cytochrome P450 family 2 subfamily C polypeptide 19
Genes
HSA: 1557(CYP2C19) 1559(CYP2C9)
PTR: 100616515(CYP2C9) 740956(CYP2C19)
PPS: 100995695 100996034
PON: 100450749
NLE: 100601437
MCF: 102147103(CYP2C75)
CSAB: 103216299(CYP2C19)
RRO: 104666123
CJC: 100389947(CYP2C19)
SBQ: 101041912
TUP: 102501371
ECB: 100061542
MYD: 102759998
MDO: 100023149
SHR: 100915447
 » show all
Taxonomy
Reference
1  [PMID:9662532]
  Authors
Bouwmeester HJ, Gershenzon J, Konings MC, Croteau R.
  Title
Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway. I. Demonstration Of enzyme activities and their changes with development
  Journal
Plant Physiol 117:901-12 (1998)
Reference
2
  Authors
Bouwmeester, H.J., Konings, M.C.J.M., Gershenzon, J., Karp, F. and Croteau, R.
  Title
Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum carvi).
  Journal
Phytochemistry 50:243-248 (1999)
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.53
IUBMB Enzyme Nomenclature: 1.14.14.53
ExPASy - ENZYME nomenclature database: 1.14.14.53
BRENDA, the Enzyme Database: 1.14.14.53
CAS: 221461-49-0

DBGET integrated database retrieval system