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
-
trans-carveol
- limonene-3-hydroxylase
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regiochemistry
- hydroxylases
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geranyl
-
p-menthane
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conversions
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perillyl
-
facial
- carveol
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p450-catalyzed
- piperita
-
allylic
-
monoterpenoids
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stereochemistry
-
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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Natural Substrates Products
Natural Substrates Products on EC 1.14.14.51 - (S)-limonene 6-monooxygenase
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REACTION DIAGRAM
(-)-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
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(-)-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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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
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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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