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 degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K17719  cytochrome P450 family 2 subfamily C9
K17721  cytochrome P450 family 2 subfamily C19
Genes
HSA1557(CYP2C19) 1559(CYP2C9)
PTR100616515(CYP2C9) 740956(CYP2C19)
PPS100995695(CYP2C19) 100996034(CYP2C9)
GGO101126456 101151965
PON100439483 100450749
NLE100591471 100601437
HMH116457268 116457271
MCC678686(CYP2C75) 678695(CYP2C9)
MCF102115450(CYP2C9) 102147103(CYP2C19)
MTHB126962028 126962032
MNI105479916 105479949
CSAB103216299(CYP2C19) 103216301(CYP2C9)
CATY105575618 105581138 105586929 105586938
PANU100997824 101012978
TGE112631549 112631550
MLEU105534699 105534700 105535382 105536626
RRO104665355 104666123
TFN117083900 117092015
PTEH111531037 111552212
CANG105501587 105504516 105504517
CJC100389947(CYP2C19)
SBQ101041912
CIMI108281686(CYP2C19)
CSYR103277060
PCOQ105822723
OGA100950266
DORD106001520
NCAR124985776
MMMA107149734
GAS123236335 123238232
 » 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

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