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Ligand ent-kaurene

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Biosynthesis of plant hormones, Biosynthesis of secondary metabolites, Biosynthesis of terpenoids and steroids, Diterpenoid biosynthesis

MetaCyc

ent -kaurene biosynthesis II, ent-kaurene biosynthesis I, gibberellin A12 biosynthesis, gibberellin biosynthesis IV (Gibberella fujikuroi), kauralexin biosynthesis, steviol biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.70

ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2 = 3alpha-hydroxy-ent-kaurene + [oxidized NADPH-hemoprotein reductase] + H2O

728514

-

1.14.14.86

ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-kaurenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

728514, 728510, 727513

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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

4.2.3.19

ent-copalyl diphosphate = ent-kaur-ene + diphosphate

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-

4.2.3.19

ent-copalyl diphosphate = 16alpha-hydroxykaurane + ent-kaurene + diphosphate

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-

4.2.3.19

ent-copalyl diphosphate = ent-beyerene + ent-kaurene + diphosphate

-

-

4.2.3.19

ent-copalyl diphosphate = ent-kaurene + diphosphate

492244, 492243, 492252, 492242, 492245, , 492240, 492250, 492249, 492241, 492247, 492246, 492251, 492248

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4.2.3.19

4 entries

5.5.1.13

copalyl diphosphate = ent-kaurene + diphosphate

492243

-

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.123

ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2 = ?

717875

-

1.14.14.70

ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2 = 3alpha-hydroxy-ent-kaurene + [oxidized NADPH-hemoprotein reductase] + H2O

728514

-

1.14.14.86

ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-kaurenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

728514, 728510, 727513

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Product in Enzyme-catalyzed Reactions (9 results)

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Show Product (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.3.19

ent-copalyl diphosphate = ent-kaur-ene + diphosphate

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-

4.2.3.19

8beta-hydroxy-ent-copalyl diphosphate = ent-13-epi-manoyl oxide + ent-kaurene + diphosphate

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-

4.2.3.19

ent-copalyl diphosphate = 16alpha-hydroxykaurane + ent-kaurene + diphosphate

-

-

4.2.3.19

ent-copalyl diphosphate = ent-beyerene + ent-kaurene + diphosphate

-

-

4.2.3.19

ent-copalyl diphosphate = ent-kaurene + diphosphate

492243, 492248, 492252, 492242, 492245, 492240, 492251, , 492246, 492247, 492241, 492249, 492250, 492244

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4.2.3.19

geranylgeranyl diphosphate = ent-kaurene + diphosphate

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-

5.5.1.13

copalyl diphosphate = ent-16-alpha-hydroxy-kaurene + ent-kaurene

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-

5.5.1.13

copalyl diphosphate = ent-kaurene + diphosphate

, 492247, 492242, 492252, 492243

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5.5.1.13

geranylgeranyl diphosphate = ent-kaurene

492248, 492247

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4.2.3.19

6 entries

5.5.1.13

3 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.123

0.009

-

pH and temperature not specified in the publication

717875

1.14.14.70

0.022

-

pH and temperature not specified in the publication

728514

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

1.14.14.123

0.005

-

pH and temperature not specified in the publication

717875

1.14.14.70

0.007

-

pH and temperature not specified in the publication

728514

References & Links

Literature References (17)

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Show Reference (17 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

492240

4331199

Purification and properties of kaurene synthetase from Fusarium moniliforme

1971

Fall, R.R.; West, C.A.

J. Biol. Chem.

246

6913-6928

492241

8771778

Molecular cloning and characterization of a cDNA encoding the gibberellin biosynthetic enzyme ent-kaurene synthase B from pumpkin (Cucurbita maxima L.)

1996

Yamaguchi, S.; Saito, T.; Abe, H.; Yamane, H.; Murofushi, N.; Kamiya, Y.

Plant J.

10

203-213

492242

9268298

ent-Kaurene synthetase from the fungus Phaeosphaeria sp. L487. cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase in fungal gibberellin biosynthesis

1997

Kawaide, H.; Imai, R.; Sassa, T.; Kamiya, Y.

J. Biol. Chem.

272

21706-21712

492243

10803977

Cloning of a full-length cDNA encoding ent-kaurene synthase from Gibberella fujikuroi: functional analysis of a bifunctional diterpene cyclase

2000

Toyomasu, T.; Kawaide, H.; Ishizaki, A.; Shinoda, S.; Otsuka, M.; Mitsuhashi, W.; Sassa, T.

Biosci. Biotechnol. Biochem.

64

660-664

492244

16659781

Properties of kaurene synthetase from Marah macrocarpus

1977

Frost, R.G.; West, C.A.

Plant Physiol.

59

22-29

492245

16662063

Properties of kaurene synthetase from Marah macrocarpus endosperm: evidence for the participation of separate but interacting enzymes

1981

Duncan, J.D.; West, C.A.

Plant Physiol.

68

1128-1134

492246

16663438

Kaurene synthetase activity in Helianthus annuus. Increases in enzyme activity after storage of seedlings in liquid nitrogen

1984

Shen-Miller, J.; West, C.A.

Plant Physiol.

74

439-441

492247

-

Distribution and ent-kaurene synthetase in Helianthus annuus and Marah macrocarpus

1985

Shen-Miller, J.; West, C.A.

Phytochemistry

24

461-464

492248

-

ent-Kaurene biosynthesis in a cell-free system from wheat (Triticum aestivum L.) seedlings and the localization of ent-kaurene synthetase in plastids of three species

1995

Aach, H.; Boese, G.; Graebe, J.E.

Planta

197

333-342

492249

12228665

Purification and properties of ent-kaurene synthase B from immature seeds of pumpkin

1995

Saito, T.; Abe, H.; Yamane, H.; Sakurai, A.; Murofushi, N.; Takio, K.; Takahashi, N.; Kamiya, Y.

Plant Physiol.

109

1239-1245

492250

-

Inhibition of ent-kaurene synthase by quaternary ammonium growth retardants

1996

Saito, T.; Yamane, H.; Sakurai, A.; Murofushi, N.; Takahashi, N.; Kamiya, Y.

Biosci. Biotechnol. Biochem.

60

1040-1042

492251

-

ent-Kaurene synthase is located in proplastids of meristematic shoot tissues

1997

Aach, H.; Bode, H.; Robinson, D.G.; Graebe, J.E.

Planta

202

211-219

492252

10644675

Functional analysis of the two interacting cyclase domains in ent-kaurene synthase from the fungus Phaeosphaeria sp. L487 and a comparison with cyclases from higher plants

2000

Kawaide, H.; Sassa, T.; Kamiya, Y.

J. Biol. Chem.

275

2276-2280

717875

22215681

Characterization of CYP76M5-8 indicates metabolic plasticity within a plant biosynthetic gene cluster

2012

Wang, Q.; Hillwig, M.; Okada, K.; Yamazaki, K.; Wu, Y.; Swaminathan, S.; Yamane, H.; Peters, R.

J. Biol. Chem.

287

6159-6168

727513

21545802

The CYP701B1 of Physcomitrella patens is an ent-kaurene oxidase that resists inhibition by uniconazole-P

2011

Miyazaki, S.; Katsumata, T.; Natsume, M.; Kawaide, H.

FEBS Lett.

585

1879-1883

728510

21994349

Evolution of diterpene metabolism: Sitka spruce CYP720B4 catalyzes multiple oxidations in resin acid biosynthesis of conifer defense against insects

2011

Hamberger, B.; Ohnishi, T.; Hamberger, B.; Seguin, A.; Bohlmann, J.

Plant Physiol.

157

1677-1695

728514

22247270

CYP701A8: a rice ent-kaurene oxidase paralog diverted to more specialized diterpenoid metabolism

2012

Wang, Q.; Hillwig, M.L.; Wu, Y.; Peters, R.J.

Plant Physiol.

158

1418-1425

Links to other databases for ent-kaurene

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Show Links (1 entry)

ChEBI

PubChem

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