KEGG   ENZYME: 4.2.3.9
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
Sysname
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)
Reaction(IUBMB)
(2E,6E)-farnesyl diphosphate = aristolochene + diphosphate [RN:R02307]
Reaction(KEGG)
R02307
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
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14180  aristolochene synthase
Genes
PANPODANSg557
PBELQC761_511740
PPSDQC762_511740
PPSPQC763_511740
PPSAQC764_511740
PCHMVFPPC_14851
AMUSLMH87_003795
CHIGCH63R_06527
MBEMBM_07677
ANIANIA_03277
ACTACLA_063920
AORAO090011000103
PCSN7525_001920
PDPPDIP_86810
BSCCOCSADRAFT_348577
NPAUCRNP2_5881
 » show all
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 112:3209-3210 (1990)
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 111:8914-8916 (1989)
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 272:137-43 (1989)
DOI:10.1016/0003-9861(89)90204-X
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 268:4543-8 (1993)
  Sequence
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 124:11636-41 (2002)
DOI:10.1021/ja020762p
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.9
IUBMB Enzyme Nomenclature: 4.2.3.9
ExPASy - ENZYME nomenclature database: 4.2.3.9
BRENDA, the Enzyme Database: 4.2.3.9
CAS: 94185-89-4
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