KEGG   ENZYME: 4.2.3.17Help
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
BRITE hierarchy
Sysname
geranylgeranyl-diphosphate diphosphate-lyase (cyclizing; taxa-4,11-diene-forming)
Reaction(IUBMB)
geranylgeranyl diphosphate = taxa-4,11-diene + diphosphate [RN:R06305]
Reaction(KEGG)
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
Diterpenoid biosynthesis
Metabolic pathways
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 (1995) 8686-90.
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 (1995) 437-44.
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 (1996) 2968-77.
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 (1997) 185-90.
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 (2000) 969-77.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
169277-52-5

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