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(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(-)-(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(-)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
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-
?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
53% the rate of (-)-limonene hydroxylation
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?
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
hydroxylation at 50%
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?
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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i.e. (+)-8,9-dihydro-limonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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limonene 6-hydroxylase mutant F363I
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-
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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highly specific, regiospecific and stereospecific reaction
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
highly specific, regiospecific and stereospecific reaction
-
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
highly specific, regiospecific and stereospecific reaction
-
?
(-)-(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
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?
(-)-(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
the enzyme is involved in biosynthesis of peppermint essential oil monoterpenes
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?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
i.e. (-)-8,9-dihydrolimonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
-
?
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
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, highly specific, absolute requirement for a reduced pyridine nucleotide and molecular oxygen
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?
additional information
?
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the kinetically competent recombinant protein produces a mixture of C3-, C6- and C7-hydroxylated limonene derivatives, i.e. (-)-perillyl alcohol, (-)-trans-isopiperitenol, and (-)-trans-carveol, with a distribution of 33%, 14% and 53%, respectively, thus it performs the reaction of EC 1.14.13.47 and 1.14.13.48, overview
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Karp, F.; Mihaliak, C.A.; Harris, J.L.; Croteau, R.
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves
Arch. Biochem. Biophys.
276
219-226
1990
Mentha x piperita
brenda
Croteau, R.; Karp, F.; Wagschal, K.C.; Satterwhite, M.; Hyatt, D.C.; Skotland, C.B.
Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content
Plant Physiol.
96
744-752
1991
Mentha x piperita, Mentha x gracilis
brenda
Gershenzon, J.; McCaskill, D.; Rajaonarivony, J.I.; Mihaliak, C.; Karp, F.; Croteau, R.
Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products
Anal. Biochem.
200
130-138
1992
Mentha x piperita
brenda
Schalk, M.; Croteau, R.
A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase
Proc. Natl. Acad. Sci. USA
97
11948-11953
2000
Mentha spicata
brenda
Lupien, S.; Karp, F.; Wildung, M.; Croteau, R.
Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (-)-4S-limonene-3-hydroxylase and (-)-4S-limonene-6-hydroxylase
Arch. Biochem. Biophys.
368
181-192
1999
Mentha x piperita
brenda
Haudenschild, C.; Schalk, M.; Karp, F.; Croteau, R.
Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and Saccharomyces cerevisiae
Arch. Biochem. Biophys.
379
127-136
2000
Mentha x piperita
brenda
Wust, M.; Little, D.B.; Schalk, M.; Croteau, R.
Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from Mint (Mentha) species: Evidence for catalysis within sterically constrained active sites
Arch. Biochem. Biophys.
387
125-136
2001
Mentha x piperita
brenda
Bertea, C.; Schalk, M.; Mau, C.J.; Karp, F.; Wildung, M.R.; Croteau, R.
Molecular evaluation of a spearmint mutant altered in the expression of limonene hydroxylases that direct essential oil monoterpene biosynthesis
Phytochemistry
64
1203-1211
2003
Mentha x gracilis
brenda
Mahmoud, S.S.; Williams, M.; Croteau, R.
Cosuppression of limonene-3-hydroxylase in peppermint promotes accumulation of limonene in the essential oil
Phytochemistry
65
547-554
2004
Mentha x piperita
brenda
Dolzhenko, Y.; Bertea, C.M.; Occhipinti, A.; Bossi, S.; Maffei, M.E.
UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha x piperita L.)
J. Photochem. Photobiol. B Biol.
100
67-75
2010
Mentha x piperita
brenda
Mau, C.J.; Karp, F.; Ito, M.; Honda, G.; Croteau, R.B.
A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens
Phytochemistry
71
373-379
2010
Perilla frutescens
brenda
Wriessnegger, T.; Moser, S.; Emmerstorfer-Augustin, A.; Leitner, E.; Mueller, M.; Kaluzna, I.; Schuermann, M.; Mink, D.; Pichler, H.
Enhancing cytochrome P450-mediated conversions in P. pastoris through RAD52 over-expression and optimizing the cultivation conditions
Fungal Genet. Biol.
89
114-125
2016
Mentha x piperita (Q9XHE7), Mentha x piperita
brenda