KEGG ENZYME: 1.14.14.106

ENZYME: 1.14.14.106

Entry

EC 1.14.14.106              Enzyme

Name

taxane 13alpha-hydroxylase;
CYP725A2 (gene name)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

taxa-4(20),11-dien-5alpha-ol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (13alpha-hydroxylating)

Reaction(IUBMB)

taxa-4(20),11-dien-5alpha-ol + [reduced NADPH---hemoprotein reductase] + O2 = taxa-4(20),11-dien-5alpha,13alpha-diol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R06308]

Reaction(KEGG)

R06308

Substrate

taxa-4(20),11-dien-5alpha-ol [CPD:C11895];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]

Product

taxa-4(20),11-dien-5alpha,13alpha-diol;
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]

Comment

This cytochrome-P-450(heme-thiolate) enzyme from the plant Taxus cuspidata is involved in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel).

History

EC 1.14.14.106 created 2002 as EC 1.14.13.77, transferred 2018 to EC 1.14.14.106

Pathway

ec00904

Diterpenoid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K12922

taxane 13alpha-hydroxylase

Reference

1 [PMID:11396929]

Authors

Wheeler AL, Long RM, Ketchum RE, Rithner CD, Williams RM, Croteau R.

Title

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

Journal

Arch Biochem Biophys 390:265-78 (2001)
DOI:10.1006/abbi.2001.2377

Reference

2 [PMID:11707604]

Authors

Jennewein S1, Rithner CD, Williams RM, Croteau RB

Title

Taxol biosynthesis: taxane 13 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase.

Journal

Proc Natl Acad Sci U S A 98:13595-600 (2001)
DOI:10.1073/pnas.251539398

Sequence

[ag:AAL23619]