KEGG   ENZYME: 1.14.13.48Help
Entry
EC 1.14.13.48               Enzyme                                 

Name
(S)-limonene 6-monooxygenase;
(-)-limonene 6-hydroxylase;
(-)-limonene 6-monooxygenase;
(-)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
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
(S)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
(S)-limonene + NADPH + H+ + O2 = (-)-trans-carveol + NADP+ + H2O [RN:R02468]
Reaction(KEGG)
Substrate
(S)-limonene;
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(-)-trans-carveol [CPD:C00964];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
High specificity, but NADH can act instead of NADPH, but more slowly. A heme-thiolate protein (P-450).
History
EC 1.14.13.48 created 1992, modified 2003
Pathway
Monoterpenoid biosynthesis
Limonene and pinene degradation
Orthology
K07381  
(S)-limonene 6-monooxygenase
K14732  
limonene hydroxylase
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: 
PPS: 
PON: 
MCF: 
102147103(CYP2C75)
TUP: 
MYD: 
Taxonomy
Reference
1  [PMID:2297225]
  Authors
Karp F, Mihaliak CA, Harris JL, Croteau R.
  Title
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.
  Journal
Arch. Biochem. Biophys. 276 (1990) 219-26.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
UM-BBD (Biocatalysis/Biodegradation Database): 
BRENDA, the Enzyme Database: 
CAS: 
138066-93-0

KEGG   ENZYME: 1.14.13.49Help
Entry
EC 1.14.13.49               Enzyme                                 

Name
(S)-limonene 7-monooxygenase;
(-)-limonene 7-monooxygenase;
(-)-limonene hydroxylase;
(-)-limonene monooxygenase;
(-)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating)
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
(S)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating)
Reaction(IUBMB)
(S)-limonene + NADPH + H+ + O2 = (-)-perillyl alcohol + NADP+ + H2O [RN:R02470]
Reaction(KEGG)
Substrate
(S)-limonene;
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(-)-perillyl alcohol [CPD:C02452];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
High specificity, but NADH can act instead of NADPH, although more slowly. A heme-thiolate protein (P-450).
History
EC 1.14.13.49 created 1992, modified 2003
Pathway
Monoterpenoid biosynthesis
Limonene and pinene degradation
Biosynthesis of secondary metabolites
Orthology
K07382  
(S)-limonene 7-monooxygenase
K14732  
limonene hydroxylase
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: 
PPS: 
PON: 
MCF: 
102147103(CYP2C75)
TUP: 
MYD: 
Taxonomy
Reference
1  [PMID:2297225]
  Authors
Karp F, Mihaliak CA, Harris JL, Croteau R.
  Title
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.
  Journal
Arch. Biochem. Biophys. 276 (1990) 219-26.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
UM-BBD (Biocatalysis/Biodegradation Database): 
BRENDA, the Enzyme Database: 
CAS: 
122653-75-2

KEGG   ENZYME: 1.14.13.80Help
Entry
EC 1.14.13.80               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 NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
(R)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
(R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Reaction(KEGG)
Substrate
(R)-limonene;
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(+)-trans-carveol [CPD:C11409];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
The reaction is stereospecific with over 95% yield of (+)-trans-carveol from (R)-limonene. (S)-Limonene, the substrate for EC 1.14.13.48, (S)-limonene 6-monooxygenase, is not a substrate. Forms part of the carvone biosynthesis pathway in Carum carvi (caraway) seeds.
History
EC 1.14.13.80 created 2003
Pathway
Monoterpenoid biosynthesis
Limonene and pinene degradation
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: 
PPS: 
PON: 
MCF: 
102147103(CYP2C75)
TUP: 
MYD: 
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 (1998) 901-12.
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 (1999) 243-248.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
221461-49-0

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