KEGG   ENZYME: 4.2.3.9Help
Entry
EC 4.2.3.9                  Enzyme                                 

Name
aristolochene synthase;
sesquiterpene cyclase;
trans,trans-farnesyl diphosphate aristolochene-lyase;
trans,trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
BRITE hierarchy
Sysname
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)
Reaction(IUBMB)
(2E,6E)-farnesyl diphosphate = aristolochene + diphosphate [RN:R02307]
Reaction(KEGG)
Substrate
(2E,6E)-farnesyl diphosphate [CPD:C00448]
Product
aristolochene [CPD:C02004];
diphosphate [CPD:C00013]
Comment
The initial internal cyclization produces the monocyclic intermediate germacrene A; further cyclization and methyl transfer converts the intermediate into aristolochene. While in some species germacrene A remains as an enzyme-bound intermediate, it has been shown to be a minor product of the reaction in Penicillium roqueforti [5] (see also EC 4.2.3.23, germacrene-A synthase). The enzyme from Penicillium roqueforti requires Mg2+. Mn2+ can partially substitute, at low concentrations. Aristolochene is the likely parent compound for a number of sesquiterpenes produced by filamentous fungi.
History
EC 4.2.3.9 created 1992 as EC 2.5.1.40, transferred 1999 to EC 4.1.99.7, transferred 2000 to EC 4.2.3.9, modified 2006
Pathway
Sesquiterpenoid and triterpenoid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K14180  
aristolochene synthase
Genes
PAN: 
ANI: 
AOR: 
AOR_1_182054(AO090011000103)
ACT: 
PCS: 
Taxonomy
Reference
1
  Authors
Cane, D.E., Prabhakaran, P.C., Oliver, J.S. and McIlwaine, D.B.
  Title
Aristolochene biosynthesis. Stereochemistry of the deprotonation steps in the enzymatic cyclization of farnesyl pyrophosphate.
  Journal
J. Am. Chem. Soc. 112 (1990) 3209-3210.
Reference
2
  Authors
Cane, D.E., Prabhakaran, P.C., Salaski, E.J., Harrison, P.M.H., Noguchi, H. and Rawlings, B.J.
  Title
Aristolochene biosynthesis and enzymatic cyclization of farnesyl pyrophosphate.
  Journal
J. Am. Chem. Soc. 111 (1989) 8914-8916.
Reference
3  [PMID:2544140]
  Authors
Hohn TM, Plattner RD.
  Title
Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti.
  Journal
Arch. Biochem. Biophys. 272 (1989) 137-43.
  Organism
Penicillium roqueforti
Reference
4  [PMID:8440737]
  Authors
Proctor RH, Hohn TM.
  Title
Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti.
  Journal
J. Biol. Chem. 268 (1993) 4543-8.
  Organism
Penicillium roqueforti
  Sequence
[up:Q03471]
Reference
5  [PMID:12296728]
  Authors
Calvert MJ, Ashton PR, Allemann RK.
  Title
Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene.
  Journal
J. Am. Chem. Soc. 124 (2002) 11636-41.
  Organism
Penicillium roqueforti
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
94185-89-4

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