KEGG   ENZYME: 1.14.14.176
Entry
EC 1.14.14.176              Enzyme                                 

Name
taxadiene 5alpha-hydroxylase
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-4,11-diene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (5alpha-hydroxylating)
Reaction(IUBMB)
taxa-4,11-diene + [reduced NADPH---hemoprotein reductase] + O2 = taxa-4(20),11-dien-5alpha-ol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R06306]
Reaction(KEGG)
R06306
Substrate
taxa-4,11-diene [CPD:C11894];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
taxa-4(20),11-dien-5alpha-ol [CPD:C11895];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
This microsomal cytochrome-P-450 (heme-thiolate) enzyme is involved in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel). The reaction includes rearrangement of the 4(5)-double bond to a 4(20)-double bond, possibly through allylic oxidation.
History
EC 1.14.14.176 created 2002 as 1.14.99.37, transferred 2020 to EC 1.14.14.176
Pathway
ec00904  Diterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14039  taxadiene 5alpha-hydroxylase
Reference
1  [PMID:8807878]
  Authors
Hefner J, Rubenstein SM, Ketchum RE, Gibson DM, Williams RM, Croteau R
  Title
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.
  Journal
Chem Biol 3:479-89 (1996)
DOI:10.1016/s1074-5521(96)90096-4
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.176
IUBMB Enzyme Nomenclature: 1.14.14.176
ExPASy - ENZYME nomenclature database: 1.14.14.176
BRENDA, the Enzyme Database: 1.14.14.176
CAS: 9035-51-2

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