KEGG   ENZYME: 1.14.14.53
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
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)
R06119
Substrate
(R)-limonene [CPD:C06099];
[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 C9
K17721  cytochrome P450 family 2 subfamily C19
Genes
HSA: 1557(CYP2C19) 1559(CYP2C9)
PTR: 100616515(CYP2C9) 740956(CYP2C19)
PPS: 100995695 100996034
GGO: 101126456 101151965
PON: 100439483 100450749
NLE: 100591471 100601437
MCC: 678686(CYP2C75) 678695(CYP2C9)
MCF: 102115450(CYP2C43) 102147103(CYP2C75)
CSAB: 103216299(CYP2C19) 103216301(CYP2C9)
RRO: 104665355 104666123
CJC: 100389947(CYP2C19)
SBQ: 101041912
 » show all
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)
DOI:10.1104/pp.117.3.901
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

KEGG   REACTION: R06119
Entry
R06119                      Reaction                               

Name
(R)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
Definition
(R)-Limonene + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (+)-trans-Carveol + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC00723  C06099_C11409
Enzyme
Pathway
rn00902  Monoterpenoid biosynthesis
rn00903  Limonene and pinene degradation
rn01110  Biosynthesis of secondary metabolites
Other DBs
RHEA: 18960

DBGET integrated database retrieval system