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Ligand taxa-4,11-diene

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for taxa-4,11-diene

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.176

taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2 = 5(12)-oxa-3(11)-cyclotaxane + [oxidized NADPH-hemoprotein reductase] + H2O

687790

-

1.14.14.176

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11(12)-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

743935

-

1.14.14.176

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

440248, 440288, 743911, 687790, 743915, 746375, 440286

-

1.14.14.176

taxadiene + [reduced NADPH-hemoprotein reductase] + O2 = taxadiene-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

744544

-

1.14.14.176

4 entries

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.3.17

(E,E,E)-geranylgeranyl diphosphate = taxa-4(5),11(12)-diene + diphosphate

0

-

4.2.3.17

geranylgeranyl diphosphate = taxa-4(5),11(12)-diene + diphosphate

0

-

4.2.3.17

geranylgeranyl diphosphate = taxa-4,11-diene + diphosphate

0, 492239, 492232, 492234, 492235, 492236, 492237, 492238, 492233

-

4.2.3.17

3 entries

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.176

taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2 = 5(12)-oxa-3(11)-cyclotaxane + [oxidized NADPH-hemoprotein reductase] + H2O

687790

-

1.14.14.176

taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11(12)-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

658425

-

1.14.14.176

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11(12)-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

743935

-

1.14.14.176

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

440248, 440288, 743911, 687790, 743915, 746375, 440286

-

1.14.14.176

taxadiene + [reduced NADPH-hemoprotein reductase] + O2 = taxadiene-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O

744544

-

1.14.14.176

5 entries

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.3.17

(E,E,E)-geranylgeranyl diphosphate = taxa-4(5),11(12)-diene + diphosphate

0

-

4.2.3.17

geranylgeranyl diphosphate = taxa-4(5),11(12)-diene + diphosphate

492232, 492234, 492235, 492236, 492237, 492238, 492239, 492233, 0

-

4.2.3.17

(E,E,E)-geranylgeranyl diphosphate = taxa-4,11-diene + diphosphate

0

-

4.2.3.17

geranylgeranyl diphosphate = taxa-4,11-diene + diphosphate

0, 492239, 492232, 492234, 492235, 492236, 492237, 492238, 492233

-

4.2.3.17

4 entries

Enzyme Kinetic Parameters

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.14.176

0.006

-

approx. value

440286

1.14.14.176

0.0069

-

-

687790

1.14.14.176

0.024

-

pH 7.5

658425

1.14.14.176

3 entries

References & Links

Literature References (18)

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Show Reference (18 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

440248

11396929

Taxol biosynthesis: differential transformations of taxadien-5alpha-ol and its acetate ester by cytochrome P450 hydroxylases from Taxus suspension cells

2001

Wheeler, A.L.; Long, R.M.; Ketchum, R.E.B.; Rithner, C.D.; Williams, R.M.; Croteau, R.

Arch. Biochem. Biophys.

390

265-278

440286

8807878

Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5alpha-ol: the first oxygenation step in taxol biosynthesis

1996

Hefner, J.; Rubenstein, S.M.; Ketchum, R.E.B.; Gibson, D.M.; Williams, R.M.; Croteau, R.

Chem. Biol.

3

479-489

440288

11524108

Taxol biosynthetic genes

2001

Walker, K.; Croteau, R.

Phytochemistry

58

1-7

492232

9016812

Taxol production and taxadiene synthase activity in Taxus canadensis cell suspension cultures

1997

Hezari, M.; Ketchum, R.E.B.; Gibson, D.M.; Croteau, R.

Arch. Biochem. Biophys.

337

185-190

492233

8621577

A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis

1996

Wildung, M.R.; Croteau, R.

J. Biol. Chem.

271

9201-9204

492234

7721772

Cyclization of geranylgeranyl diphosphateto taxa-4(5),-11(12)-diene is the comitted step of taxol biosynthesis in pacific yew

1995

Koepp, A.E.; Hezari, M.; Zajicek, J.; Stofer Vogel, B.; LaFever, R.; Lewis, N.G.; Croteau, R.

J. Biol. Chem.

270

8686-8690

492235

8608134

Mechanism of taxadiene synthase, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in pacific yew

1996

Lin, X.; Hezari, M.; Koepp, A.E.; Floss, H.G.; Croteau, R.

Biochemistry

35

2968-2977

492236

11137819

Intramolecular proton transfer in the cyclization of geranylgeranyl diphosphate to the taxadiene precursor of taxol catalyzed by recombinant taxadiene synthase

2000

Williams, D.C.; Carroll, B.J.; Jin, Q.; Rithner, C.D.; Lenger, S.R.; Floss, H.G.; Coates, R.M.; Williams, R.M.; Croteau, R.

Chem. Biol.

7

969-977

492237

10864451

Heterologous xpression and characterization of a "Pseudomature" form of taxadiene synthase involved in paclitaxel (taxol) biosynthesis and evaluation of a potential intermediate and inhibitors of the multistep diterpene cyclization reaction

2000

Williams, D.C.; Wildung, M.R.; Jin, A.Q.; Dalal, D.; Oliver, J.S.; Coates, R.M.; Croteau, R.

Arch. Biochem. Biophys.

379

137-146

492238

11553461

Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol

2001

Huang, Q.; Roessner, C.A.; Croteau, R.; Scott, A.I.

Bioorg. Med. Chem.

9

2237-2242

492239

-

Sesquiterpenes produced by truncated taxadiene synthase

2000

Huang, Q.; Williams, H.J.; Roessner, C.A.; Scott, A.I.

Tetrahedron Lett.

41

9701-9704

658425

15123267

Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis

2004

Jennewein, S.; Long, R.M.; Williams, R.M.; Croteau, R.

Chem. Biol.

11

379-387

687790

18167342

CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the yclic ether 5(12)-oxa-3(11)-cyclotaxane

2008

Rontein, D.; Onillon, S.; Herbette, G.; Lesot, A.; Werck-Reichhart, D.; Sallaud, C.; Tissier, A.

J. Biol. Chem.

283

6067-6075

743911

26930136

Orthogonal assays clarify the oxidative biochemistry of taxol P450 CYP725A4

2016

Biggs, B.W.; Rouck, J.E.; Kambalyal, A.; Arnold, W.; Lim, C.G.; De Mey, M.; ONeil-Johnson, M.; Starks, C.M.; Das, A.; Ajikumar, P.K.

ACS Chem. Biol.

11

1445-1451

743915

26677870

Mechanistic insights into taxadiene epoxidation by taxadiene-5alpha-hydroxylase

2016

Edgar, S.; Zhou, K.; Qiao, K.; King, J.R.; Simpson, J.H.; Stephanopoulos, G.

ACS Chem. Biol.

11

460-469

743935

27794603

Engineering of taxadiene synthase for improved selectivity and yield of a key taxol biosynthetic intermediate

2017

Edgar, S.; Li, F.S.; Qiao, K.; Weng, J.K.; Stephanopoulos, G.

ACS Synth. Biol.

6

201-205

744544

28876471

Taxadiene-5alpha-ol is a minor product of CYP725A4 when expressed in Escherichia coli

2018

Sagwan-Barkdoll, L.; Anterola, A.M.

Biotechnol. Appl. Biochem.

65

294-305

746375

28109855

Heterologous expression and characterization of plant taxadiene-5alpha-hydroxylase (CYP725A4) in Escherichia coli

2017

Rouck, J.E.; Biggs, B.W.; Kambalyal, A.; Arnold, W.R.; De Mey, M.; Ajikumar, P.K.; Das, A.

Protein Expr. Purif.

132

60-67

Links to other databases for taxa-4,11-diene

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Show Links (1 entry)

ChEBI

PubChem