1.14.14.176: taxadiene 5alpha-hydroxylase

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For detailed information about taxadiene 5alpha-hydroxylase, go to the full flat file.

Reaction

Synonyms

5alphaCYP, CYP725A4, EC 1.14.99.37, oxygenase, taxadiene 5-mono-, taxa-4(5),11(12)-diene 5-hydroxylase, taxa-4(5),11(12)-diene 5alpha-hydroxylase, taxadien-5alpha-hydroxylase, taxadiene 5-hydroxylase, taxadiene 5-monooxygenase, taxadiene synthase, taxadiene-5alpha-hydroxylase

ECTree

     1 Oxidoreductases

         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

             1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

                1.14.14.176 taxadiene 5alpha-hydroxylase

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Results	in table
4	Activating Compound
7	AA Sequence
7	Application
1	CAS Registry Number
6	Cloned(Commentary)
3	Cofactor
8	Inhibitors
5	KM Value [mM]
5	Localization
14	Natural Substrates/ Products (Substrates)
14	Organism
6	Pathway
2	pH Optimum
2	Purification (Commentary)
5	Reaction
4	Reaction Type
14	Reference
5	Source Tissue
19	Substrates and Products (Substrate)
19	Synonyms
1	Systematic Name
1	Temperature Optimum [°C]

Substrates Products

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Substrates Products on EC 1.14.14.176 - taxadiene 5alpha-hydroxylase

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SUBSTRATE

PRODUCT                       

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

taxa-4(20),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

Q6WG30

preferred substrate

658425

-

-

?

taxa-4(20)-11(12)-diene + AH2 + O2

?

Taxus sp.

-

-

743935

-

-

?

taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2

5(12)-oxa-3(11)-cyclotaxane + [oxidized NADPH-hemoprotein reductase] + H2O

Taxus cuspidata

Q6WG30

hydroxylation of the C-5alpha is the first of the oxidations resulting in taxol

687790

OCT is a cyclic ether

-

?

taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

Q6WG30

-

658425

-

-

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus sp.

-

-

743935

-

-

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

9 entries

taxadiene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

Q6WG30

-

744544

-

-

?

additional information

?

-

2 entries

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus brevifolia

-

-

440288

-

440288

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus brevifolia

-

-

743911

-

-

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus brevifolia

-

reaction is completely dependent on NADPH

440286

-

440286

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus brevifolia

-

reaction is completely dependent on NADPH, enzyme catalyzes the first oxygenating step in taxol biosynthesis pathway

440286

-

440286

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

-

-

440248

-

440248

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

-

-

440288

-

440288

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

Q6WG30

-

687790, 743915, 746375

-

-

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

-

reaction is completely dependent on NADPH

440286

-

440286

?

taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2

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

Taxus cuspidata

-

reaction is completely dependent on NADPH, enzyme catalyzes the first oxygenating step in taxol biosynthesis pathway

440286

-

440286

?

additional information

?

-

Taxus cuspidata

Q6WG30

the recombinant enzyme produces 5(12)-oxa-3(11)-cyclotaxane, a tritiated oxidized taxane, instead of taxa-4(20),11-dien-5alpha-ol, structural analysis of the compound, overview

687790

-

-

?

additional information

?

-

Taxus cuspidata

Q6WG30

cDNAs encoding taxa-4(5),11(12)-diene synthase and CYP725A4 are introduced in Nicotiana sylvestris for specific expression in trichome cells. The co-expression does not lead to the production of the expected 5-hydroxytaxa-4(20),11(12)-diene. Instead, taxa-4(5),11(12)-diene is quantitatively converted to a novel taxane

687790

-

-

?