EC 4.2.3.9 - Aristolochene synthase

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IntEnz Enzyme Nomenclature
EC 4.2.3.9

Names

Accepted name:
aristolochene synthase
Other names:
trans,trans-farnesyl diphosphate aristolochene-lyase
sesquiterpene cyclase
trans,trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)
Systematic name:
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)

Reaction

Cofactors

Comments:

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+ and Mn2+ for activity. Aristolochene is the likely parent compound for a number of sesquiterpenes produced by filamentous fungi.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
Gene Ontology: GO:0045483
UniProtKB/Swiss-Prot:

References

  1. Cane, D.E., Prabhakaran, P.C., Oliver, J.S., McIlwaine, D.B.
    Aristolochene biosynthesis. Stereochemistry of the deprotonation steps in the enzymatic cyclization of farnesyl pyrophosphate.
    J. Am. Chem. Soc. 112: 3209-3210 (1990).
  2. Cane, D.E., Prabhakaran, P.C., Salaski, E.J., Harrison, P.M.H., Noguchi, H., Rawlings, B.J.
    Aristolochene biosynthesis and enzymatic cyclization of farnesyl pyrophosphate.
    J. Am. Chem. Soc. 111: 8914-8916 (1989).
  3. Hohn, T.M., Plattner, R.D.
    Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti.
    Arch. Biochem. Biophys. 272: 137-143 (1989). [PMID: 2544140]
  4. Proctor, R.H. and Hohn, T.M.
    Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti.
    J. Biol. Chem. 268: 4543-4548 (1993). [PMID: 8440737]
  5. Calvert, M.J., Ashton, P.R. and Allemann, R.K.
    Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene.
    J. Am. Chem. Soc. 124: 11636-11641 (2002). [PMID: 12296728]

[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]