ExplorEnz: EC 4.2.3.9

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4.2.3.9

Accepted name:

aristolochene synthase

Reaction:

(2E,6E)-farnesyl diphosphate = aristolochene + diphosphate

For diagram of eremophilane and spirovetivane sesquiterpenoid biosynthesis, click here

Other name(s):

sesquiterpene cyclase; trans,trans-farnesyl diphosphate aristolochene-lyase; trans,trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)

Systematic name:

(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)

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⁺. Mn²⁺ can partially substitute, at low concentrations. Aristolochene is the likely parent compound for a number of sesquiterpenes produced by filamentous fungi.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 94185-89-4

References:

1.	Cane, D.E., Prabhakaran, P.C., Oliver, J.S. and McIlwaine, D.B. Aristolochene biosynthesis. Stereochemistry of the deprotonation steps in the enzymatic cyclization of farnesyl pyrophosphate. J. Am. Chem. Soc. 112 (1990) 3209–3210.
2.	Cane, D.E., Prabhakaran, P.C., Salaski, E.J., Harrison, P.M.H., Noguchi, H. and Rawlings, B.J. Aristolochene biosynthesis and enzymatic cyclization of farnesyl pyrophosphate. J. Am. Chem. Soc. 111 (1989) 8914–8916.
3.	Hohn, T.M. and Plattner, R.D. Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti. Arch. Biochem. Biophys. 272 (1989) 137–143. [DOI] [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 (1993) 4543–4548. [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 (2002) 11636–11641. [DOI] [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]