ExplorEnz: EC 4.2.3.7

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4.2.3.7

Accepted name:

pentalenene synthase

Reaction:

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

For diagram of sesquiterpenoid biosynthesis based on humulene, click here

Glossary:

pentalenene = (1R,8aR)-1,4,7,7-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene

Other name(s):

pentalenene synthetase

Systematic name:

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

Comments:

Isolated from Streptomyces avermitilis. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics. The 9si hydrogen of farnesyl diphosphate undergoes a 1,2-hydride shift where it becomes the 1α hydrogen of pentalenene.

Links to other databases:

BRENDA, EXPASY, Gene, KEGG, MetaCyc, PDB, CAS registry number: 90597-46-9

References:

1.	Cane, D.E. Cell-free studies of monoterpene and sesquiterpene biosynthesis. Biochem. Soc. Trans. 11 (1983) 510–515. [PMID: 6642060]
2.	Cane, D.E. and Tillman, A.M. Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate. J. Am. Chem. Soc. 105 (1983) 122–124.
3.	Cane, D.E., Sohng, J.K., Lamberson, C.R., Rudnicki, S.M., Wu, Z., Lloyd, M.D., Oliver, J.S. and Hubbard, B.R. Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319. Biochemistry 33 (1994) 5846–5857. [PMID: 8180213]
4.	Cane, D.E., Abell, C., Harrison, P.H., Hubbard, B.R., Kane, C.T., Lattman, R., Oliver, J.S. and Weiner, S.W. Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions. Philos. Trans. R. Soc. Lond. B Biol. Sci. 332 (1991) 123–129. [DOI] [PMID: 1678531]
5.	Lesburg, C.A., Zhai, G., Cane, D.E. and Christianson, D.W. Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science 277 (1997) 1820–1824. [DOI] [PMID: 9295272]
6.	Zu, L., Xu, M., Lodewyk, M.W., Cane, D.E., Peters, R.J. and Tantillo, D.J. Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry. J. Am. Chem. Soc. 134 (2012) 11369–11371. [DOI] [PMID: 22738258]

[EC 4.2.3.7 created 1989 as EC 4.6.1.5, transferred 2000 to EC 4.2.3.7]