Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
(-)-(4S)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
-
mutant F363I
mutant F363I
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
-
-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
(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
-
-
-
-
?
1-cyclohexene 1-methanol + NAD+
1-cyclohexen-1-carbaldehyde + NADH + H+
4-isopropyl benzyl alcohol + NAD+
4-isopropylbenzyl aldehyde + NADH
4-methyl benzyl alcohol + NAD+
? + NADH
17.1% activity compared to perillyl alcohol
-
-
?
benzyl alcohol + NAD+
benzaldehyde + NADH
carveol + NAD+
? + NADH
86% activity compared to perillyl alcohol
-
-
?
cyclohexyl methanol + NAD+
cyclohexylaldehyde + NADH
15.8% activity compared to perillyl alcohol
-
-
?
myrtenol + NAD+
myrtenal + NADH
4.0% activity compared to perillyl alcohol
-
-
?
perillyl alcohol + NAD+
perillyl aldehyde + NADH
perillyl aldehyde + NADH
perillyl alcohol + NAD+
-
-
-
r
additional information
?
-
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
-
hydroxylation at 25% the rate of (-)-limonene
-
?
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
-
radiation induced mutant 86% the rate of (-)-limonene
-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
-
i.e. (+)-8,9-dihydrolimonene, hydroxylation at 30% the rate of (-)-limonene
-
-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
-
-
-
?
(-)-(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
-
-
-
?
(-)-(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
-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
-
highly specific
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
-
highly specific
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
-
highly specific
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
-
i.e. (-)-8,9-dihydrolimonene, hydroxylation at 74% the rate of (-)-limonene
-
-
?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
-
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
-
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
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
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
-
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
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
-
-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
-
-
-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
-
-
-
?
1-cyclohexene 1-methanol + NAD+
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
-
-
?
4-isopropyl benzyl alcohol + NAD+
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
-
-
?
benzyl alcohol + NAD+
benzaldehyde + NADH
3.1% activity compared to perillyl alcohol
-
-
?
benzyl alcohol + NAD+
benzaldehyde + NADH
3.1% activity compared to perillyl alcohol
-
-
?
perillyl alcohol + NAD+
perillyl aldehyde + NADH
100% activity
-
-
r
perillyl alcohol + NAD+
perillyl aldehyde + NADH
100% activity
-
-
r
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
(4R)-limonene leads to multiple products indicating allylic rearrangement
-
-
?
additional information
?
-
-
(4R)-limonene leads to multiple products indicating allylic rearrangement
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
(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
-
-
?
additional information
?
-
-
no activity with (R)-limonene
-
-
?
additional information
?
-
-
(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
-
-
?
additional information
?
-
-
no activity with (R)-limonene
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(-)-(S)-limonene + NADPH + O2
(-)-trans-carveol + NADP+
-
-
-
-
?
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
-
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
(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
-
-
-
-
?
additional information
?
-
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
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
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
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
-
-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
-
-
-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
-
-
-
?
additional information
?
-
-
(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
-
-
?
additional information
?
-
-
(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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Gershenzon, J.; Maffei, M.; Croteau, R.
Biochemical and histochemical localization of monoterpene biosynthesis in the glandular trichomes of spearmint (Mentha spicata)
Plant Physiol.
89
1351-1357
1989
Mentha spicata
brenda
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 spicata
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 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 spicata
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 spicata (Q9XHE8), Mentha spicata
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 spicata
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 spicata
brenda
Wuest, M.; Croteau, R.B.
Hydroxylation of specifically deuterated limonene enantiomers by cytochrome P450 limonene-6-hydroxylase reveals the mechanism of multiple product formation
Biochemistry
41
1820-1827
2002
Mentha spicata
brenda
Lupien, S.; Karp, F.; Ponnamperuma, K.; Wildung, M.; Croteau, R.
Cytochrome P450 limonene hydroxylases of Mentha species
Drug Metabol. Drug Interact.
12
245-260
1995
Mentha spicata
brenda
Carter, O.A.; Peters, R.J.; Croteau, R.
Monoterpene biosynthesis pathway construction in Escherichia coli
Phytochemistry
64
425-433
2003
Mentha spicata
brenda
Shimada, T.; Shindo, M.; Miyazawa, M.
Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans
Drug Metab. Pharmacokinet.
17
507-515
2002
Canis lupus familiaris, Cavia porcellus, Oryctolagus cuniculus, Macaca fascicularis, Homo sapiens, Mus musculus, Rattus norvegicus
brenda
Turner, G.W.; Croteau, R.
Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase
Plant Physiol.
136
4215-4227
2004
Mentha spicata
brenda
Hamada, H.; Kondo, Y.; Ishihara, K.; Nakajima, N.; Kurihara, R.; Hirata, T.
Stereoselective biotransformation of limonene and limonene oxide by cyanobacterium, Synechococcus sp. PCC 7942
J. Biosci. Bioeng.
96
581-584
2003
Synechococcus sp., Synechococcus sp. PCC 7942
brenda
Cheong, T.; Oriel, P.
Cloning and expression of the limonene hydroxylase of Bacillus stearothermophilus BR388 and utilization in two-phase limonene conversions
Appl. Biochem. Biotechnol.
84-86
903-915
2000
Geobacillus stearothermophilus (O85057), Geobacillus stearothermophilus, Geobacillus stearothermophilus BR388 (O85057)
brenda
Bouwmeester, H.; Konings, M.; Gershenzon, J.; Karp, F.; Croteau, R.
Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum carvi)
Phytochemistry
50
243-248
1999
Carum carvi
-
brenda