EC 4.2.3.7 - Pentalenene synthase

  IntEnz view ENZYME view

IntEnz Enzyme Nomenclature
EC 4.2.3.7

Names

Accepted name:
pentalenene synthase
Other name:
pentalenene synthetase
Systematic name:
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)

Reaction

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

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
Gene Ontology: GO:0050467
UniProtKB/Swiss-Prot:

References

  1. Cane, D.E.
    Cell-free studies of monoterpene and sesquiterpene biosynthesis.
    Biochem. Soc. Trans. 11: 510-515 (1983). [PMID: 6642060]
  2. Cane, D.E. and Tillman, A.M.
    Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate.
    J. Am. Chem. Soc. 105: 122-124 (1983).
  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: 5846-5857 (1994). [PMID: 8180213]
  4. Cane, D. E., Abell, C., Harrison, P. H., Hubbard, B. R., Kane, C. T., Lattman, R., Oliver, J. S., Weiner, S. W.
    Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions.
    Philos. Trans. R. Soc. Lond., B, Biol. Sci. 332: 123-129 (1991). [PMID: 1678531]
  5. Lesburg, C. A., Zhai, G., Cane, D. E., Christianson, D. W.
    Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology.
    Science 277: 1820-1824 (1997). [PMID: 9295272]
  6. Zu, L., Xu, M., Lodewyk, M. W., Cane, D. E., Peters, R. J., 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: 11369-11371 (2012). [PMID: 22738258]

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