IntEnz Enzyme Nomenclature
trans,trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)
19825 [IUBMB](2E,6E)-farnesyl diphosphate(2E,6E)-farnesyl diphosphateName origin: UniProt - CHECKED (C)Formula: C15H25O7P2
Charge: -3ChEBI compound status: CHECKED (C)=(+)-aristolochene(+)-aristolocheneName origin: UniProt - CHECKED (C)Formula: C15H24
Charge: 0ChEBI compound status: CHECKED (C)
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  (see also EC 126.96.36.199, 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
Aristolochene biosynthesis. Stereochemistry of the deprotonation steps in the enzymatic cyclization of farnesyl pyrophosphate.J. Am. Chem. Soc. 112: 3209-3210 (1990).
Aristolochene biosynthesis and enzymatic cyclization of farnesyl pyrophosphate.J. Am. Chem. Soc. 111: 8914-8916 (1989).
Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti.Arch. Biochem. Biophys. 272: 137-143 (1989). [PMID: 2544140]
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]
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 188.8.131.52 created 1992 as EC 184.108.40.206, transferred 1999 to EC 220.127.116.11, transferred 2000 to EC 18.104.22.168, modified 2006]