1.14.14.51: (S)-limonene 6-monooxygenase
This is an abbreviated version!
For detailed information about (S)-limonene 6-monooxygenase, go to the full flat file.
Word Map on EC 1.14.14.51
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1.14.14.51
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spearmint
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monoterpene
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regiospecific
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peppermint
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olefin
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carvone
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mentha
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trans-carveol
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limonene-3-hydroxylase
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regiochemistry
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hydroxylases
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geranyl
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p-menthane
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conversions
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perillyl
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facial
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carveol
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p450-catalyzed
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piperita
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allylic
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monoterpenoids
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stereochemistry
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enantiomers
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stereochemical
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fad
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complementarity
- 1.14.14.51
- spearmint
-
monoterpene
-
regiospecific
- peppermint
-
olefin
- carvone
- mentha
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trans-carveol
- limonene-3-hydroxylase
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regiochemistry
- hydroxylases
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geranyl
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p-menthane
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conversions
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perillyl
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facial
- carveol
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p450-catalyzed
- piperita
-
allylic
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monoterpenoids
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stereochemistry
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enantiomers
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stereochemical
- fad
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complementarity
Reaction
Synonyms
(+)-limonene-6-hydroxylase, (-)-(4S)-limonene-6-hydroxylase, (-)-limonene 6-hydroxylase, (-)-limonene 6-monooxygenase, (-)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating), (-)-limonene-6-hydroxylase, 4S-limonene-6-hydroxylase, EC 1.14.13.48, limonene hydroxylase, limonene-6-hydroxylase, oxygenase, (-)-limonene 6-mono-
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.51 - (S)-limonene 6-monooxygenase
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REACTION DIAGRAM
(-)-(4S)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
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mutant F363I
mutant F363I
?
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
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-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
4-methyl benzyl alcohol + NAD+
? + NADH
17.1% activity compared to perillyl alcohol
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-
?
carveol + NAD+
? + NADH
86% activity compared to perillyl alcohol
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-
?
cyclohexyl methanol + NAD+
cyclohexylaldehyde + NADH
15.8% activity compared to perillyl alcohol
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-
?
myrtenol + NAD+
myrtenal + NADH
4.0% activity compared to perillyl alcohol
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-
?
perillyl aldehyde + NADH
perillyl alcohol + NAD+
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-
-
r
(+)-cis-carveol + NADP+ + H2O
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hydroxylation at 25% the rate of (-)-limonene
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?
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
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radiation induced mutant 86% the rate of (-)-limonene
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?
(+)-cis-carvotanacetol + NADP+ + H2O
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i.e. (+)-8,9-dihydrolimonene, hydroxylation at 30% the rate of (-)-limonene
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-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
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-
-
?
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
-
-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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highly specific
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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highly specific
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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highly specific
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?
(-)-trans-carvotanacetol + NADP+ + H2O
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i.e. (-)-8,9-dihydrolimonene, hydroxylation at 74% the rate of (-)-limonene
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-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
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-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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convertion of (S)-limonene to cis- and trans-carveols in cells in 11% and 9% yields, respectively, after 6 h. The cells discriminate the (R) and (S) stereoisomers of the limonene and hydroxylate regioselectively at the 6-position of the (R) form
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-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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-
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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convertion of (S)-limonene to cis- and trans-carveols in cells in 11% and 9% yields, respectively, after 6 h. The cells discriminate the (R) and (S) stereoisomers of the limonene and hydroxylate regioselectively at the 6-position of the (R) form
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-
?
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
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-
-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
-
-
-
?
1-cyclohexen-1-carbaldehyde + NADH + H+
9.6% activity compared to perillyl alcohol
-
-
?
1-cyclohexene 1-methanol + NAD+
1-cyclohexen-1-carbaldehyde + NADH + H+
9.6% activity compared to perillyl alcohol
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-
?
4-isopropylbenzyl aldehyde + NADH
42.2% activity compared to perillyl alcohol
-
-
?
4-isopropyl benzyl alcohol + NAD+
4-isopropylbenzyl aldehyde + NADH
42.2% activity compared to perillyl alcohol
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-
?
benzaldehyde + NADH
3.1% activity compared to perillyl alcohol
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-
?
benzyl alcohol + NAD+
benzaldehyde + NADH
3.1% activity compared to perillyl alcohol
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-
?
perillyl aldehyde + NADH
100% activity
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-
r
perillyl alcohol + NAD+
perillyl aldehyde + NADH
100% activity
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-
r
additional information
?
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(4R)-limonene leads to multiple products indicating allylic rearrangement
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-
?
additional information
?
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(4R)-limonene leads to multiple products indicating allylic rearrangement
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-
?
additional information
?
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no substrates: isolimonenes, terpinolene, alpha- or beta-phellandrene, alpha- or beta-terpinene, bicyclic monoterpenes: pinene, sabinene, alpha-thujene, p-cymene, cis- or trans-p-menthane, NADH can replace NADPH, but more slowly
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-
?
additional information
?
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(S)-limonene is hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also show the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. Biotransformation of (+)-limonene oxide produces (1S,2S,4R)-limonene-1,2-diol and (1S,4R)-limonene-1-ol-2-one in 32% and 16% yields, respectively, and (1R,2S,4R)-limonene oxide is recovered
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-
?
additional information
?
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-
(S)-limonene is hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also show the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. Biotransformation of (+)-limonene oxide produces (1S,2S,4R)-limonene-1,2-diol and (1S,4R)-limonene-1-ol-2-one in 32% and 16% yields, respectively, and (1R,2S,4R)-limonene oxide is recovered
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-
?