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Ligand (-)-trans-carveol

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.243

(-)-trans carveol + NADP+ = (-)-carvone + NADPH

656560, 656954

-

1.1.1.243

(4R,6S)-trans-carveol + NAD+ = (4R)-carvone + NADH

286369

-

1.1.1.243

(4R,6S)-trans-carveol + NADP+ = (4R)-carvone + NADPH

286368

-

1.1.1.243

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.51

(-)-(S)-limonene + NADPH + O2 = (-)-trans-carveol + NADP+

-

-

1.14.14.51

(-)-limonene + NADPH + O2 = (-)-trans-carveol + NADP+ + H2O

-

-

1.14.14.51

(S)-limonene + NADPH + H+ + O2 = (-)-trans-carveol + NADP+ + H2O

-

-

1.14.14.51

(S)-limonene + [reduced NADH-hemoprotein reductase] + O2 = (-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O

-

-

1.14.14.51

(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.51

5 entries

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.198

(-)-trans-carveol + NAD+ = (-)-carvone + NADH + H+

726116

-

1.1.1.243

(-)-trans carveol + NAD+ = (-)-carvone + NADH

656560

-

1.1.1.243

(-)-trans carveol + NADP+ = (-)-carvone + NADPH

656954, 656560

-

1.1.1.243

(4R,6S)-trans-carveol + NAD+ = (4R)-carvone + NADH

286371, 286369

-

1.1.1.243

(4R,6S)-trans-carveol + NADP+ = (4R)-carvone + NADPH

286368

-

1.1.1.243

4 entries

1.1.1.275

(-)-trans-carveol + NAD+ = ?

639021

-

1.3.1.102

(2S,4R)-carveol + NADP+ = (R)-carvone + NADPH + H+

287113

-

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.155

(-)-limonene + NADH + H+ + O2 = (1S,6R)-isopiperitenol + (4R,6S)-carveol + (R)-1,2-epoxy-limonene

-

-

1.14.14.51

(-)-(4S)-limonene + NADPH + O2 = (-)-(4R,6S)-trans-carveol + NADP+ + H2O

286368, 390088, 390089, 390094, 390097, 390087, 390083, 390085, 390084

-

1.14.14.51

(-)-(S)-limonene + NADPH + O2 = (-)-trans-carveol + NADP+

-

-

1.14.14.51

(-)-limonene + NADPH + O2 = (-)-trans-carveol + NADP+ + H2O

-

-

1.14.14.51

(S)-limonene + NADPH + H+ + O2 = (-)-trans-carveol + NADP+ + H2O

-

-

1.14.14.51

(S)-limonene + [reduced NADH-hemoprotein reductase] + O2 = (-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O

-

-

1.14.14.51

(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.51

6 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.155

-

745560

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.3.1.102

0.097

-

dehydrogenation, pH 8.0, 35°C, NADP+

287113

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.243

0.041

-

-

286369

1.3.1.102

1.9

-

pH 8.0, 35°C, NADP+

287113

References & Links

Literature References (17)

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Show Reference (17 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

286368

16666709

Biochemical and histochemical localization of monoterpene biosynthesis in the glandular trichomes of spearmint (Mentha spicata)

1989

Gershenzon, J.; Maffei, M.; Croteau, R.

Plant Physiol.

89

1351-1357

286369

10473585

Stereoselective carveol dehydrogenase from Rhodococcus erythropolis DCL14

1999

van der Werft, M.J.; van der Ven, C.; Barbirato, F.; Eppink, H.M.; de Bont, J.A.M.; van Berkel, W.J.H.

J. Biol. Chem.

274

26296-26304

286371

-

Development of a reaction system for the selective conversion of (-)-trans-carveol to (-)-carvone with whole cells of Rhodococcus erythropolis DCL14

2001

Tecelao, C.S.R.; van Keulen, F.; da Fonseca, M.R.

J. Mol. Catal. , B Enzym.

11

719-724

287113

11117876

A 38 kDa allylic alcohol dehydrogenase from the cultured cells of Nicotiana tabacum

2000

Hirata, T.; Tamura, Y.; Yokobatake, N.; Shimoda, K.; Ashida, Y.

Phytochemistry

55

297-303

390083

2297225

Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves

1990

Karp, F.; Mihaliak, C.A.; Harris, J.L.; Croteau, R.

Arch. Biochem. Biophys.

276

219-226

390084

16668250

Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content

1991

Croteau, R.; Karp, F.; Wagschal, K.C.; Satterwhite, M.; Hyatt, D.C.; Skotland, C.B.

Plant Physiol.

96

744-752

390085

1595887

Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products

1992

Gershenzon, J.; McCaskill, D.; Rajaonarivony, J.I.; Mihaliak, C.; Karp, F.; Croteau, R.

Anal. Biochem.

200

130-138

390087

10415126

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

1999

Lupien, S.; Karp, F.; Wildung, M.; Croteau, R.

Arch. Biochem. Biophys.

368

181-192

390088

10864450

Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and Saccharomyces cerevisiae

2000

Haudenschild, C.; Schalk, M.; Karp, F.; Croteau, R.

Arch. Biochem. Biophys.

379

127-136

390089

11368174

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

2001

Wust, M.; Little, D.B.; Schalk, M.; Croteau, R.

Arch. Biochem. Biophys.

387

125-136

390094

11827526

Hydroxylation of specifically deuterated limonene enantiomers by cytochrome P450 limonene-6-hydroxylase reveals the mechanism of multiple product formation

2002

Wuest, M.; Croteau, R.B.

Biochemistry

41

1820-1827

390097

8820855

Cytochrome P450 limonene hydroxylases of Mentha species

1995

Lupien, S.; Karp, F.; Ponnamperuma, K.; Wildung, M.; Croteau, R.

Drug Metabol. Drug Interact.

12

245-260

639021

9662532

Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway. I. Demonstration of enzyme activities and their changes with development

1998

Bouwmeester, H.J.; Gershenzon, J.; Konings, M.C.J.M.; Croteau, R.

Plant Physiol.

117

901-912

656560

-

Development of a reaction system for the selective conversion of (-)-trans-carveol to (-)-carvone with whole cells of Rhodococcus erythropolis DCL14

2001

Tecelao, C.S.R.; van Keulen, F.; da Fonseca, M.M.R.

J. Mol. Catal. B

11

719-724

656954

12943759

Monoterpene biosynthesis pathway construction in Escherichia coli

2003

Carter, O.A.; Peters, R.J.; Croteau, R.

Phytochemistry

64

425-433

726116

20621795

A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua

2010

Polichuk, D.R.; Zhang, Y.; Reed, D.W.; Schmidt, J.F.; Covello, P.S.

Phytochemistry

71

1264-1269

745560

-

Monoterpene hydroxylation with an artificial self-sufficient P450 utilizing a P450SMO reductase domain for the electron transfer

2015

Luan, Z.; Yin, Y.; Li, A.; Yu, H.; Xu, J.

J. Mol. Catal. B

116

78-82

Links to other databases for (-)-trans-carveol

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Show Links (1 entry)

ChEBI

PubChem

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