KEGG ENZYME: 4.2.3.17

ENZYME: 4.2.3.17

Entry

EC 4.2.3.17                 Enzyme

Name

taxadiene synthase;
geranylgeranyl-diphosphate diphosphate-lyase (cyclizing, taxadiene-forming)

Class

Lyases;
Carbon-oxygen lyases;
Acting on phosphates

Sysname

geranylgeranyl-diphosphate diphosphate-lyase (cyclizing; taxa-4,11-diene-forming)

Reaction(IUBMB)

geranylgeranyl diphosphate = taxa-4,11-diene + diphosphate [RN:R06305]

Reaction(KEGG)

R06305

Substrate

geranylgeranyl diphosphate [CPD:C00353]

Product

taxa-4,11-diene [CPD:C11894];
diphosphate [CPD:C00013]

Comment

This is the committed step in the biosynthesis of the diterpenoid antineoplastic drug Taxol (paclitaxel). The cyclization involves a 1,5-hydride shift.

History

EC 4.2.3.17 created 2002

Pathway

ec00904

Diterpenoid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K12921

taxadiene synthase

Reference

1 [PMID:7721772]

Authors

Koepp AE, Hezari M, Zajicek J, Vogel BS, LaFever RE, Lewis NG, Croteau R.

Title

Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the committed step of taxol biosynthesis in Pacific yew.

Journal

J Biol Chem 270:8686-90 (1995)
DOI:10.1074/jbc.270.15.8686

Reference

2 [PMID:7574719]

Authors

Hezari M, Lewis NG, Croteau R.

Title

Purification and characterization of taxa-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis.

Journal

Arch Biochem Biophys 322:437-44 (1995)
DOI:10.1006/abbi.1995.1486

Reference

3 [PMID:8608134]

Authors

Lin X, Hezari M, Koepp AE, Floss HG, Croteau R.

Title

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

Journal

Biochemistry 35:2968-77 (1996)
DOI:10.1021/bi9526239

Reference

4 [PMID:9016812]

Authors

Hezari M, Ketchum RE, Gibson DM, Croteau R.

Title

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

Journal

Arch Biochem Biophys 337:185-90 (1997)
DOI:10.1006/abbi.1996.9772

Reference

5 [PMID:11137819]

Authors

Williams DC, Carroll BJ, Jin Q, Rithner CD, Lenger SR, Floss HG, Coates RM, Williams RM, Croteau R.

Title

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

Journal

Chem Biol 7:969-77 (2000)
DOI:10.1016/S1074-5521(00)00046-6

Other DBs

ExplorEnz - The Enzyme Database:

4.2.3.17

IUBMB Enzyme Nomenclature:

4.2.3.17

ExPASy - ENZYME nomenclature database:

4.2.3.17

BRENDA, the Enzyme Database:

4.2.3.17

CAS:	169277-52-5

LinkDB

DBGET integrated database retrieval system