KEGG   ENZYME: 4.2.3.7Help
Entry
EC 4.2.3.7                  Enzyme                                 

Name
pentalenene synthase;
pentalenene synthetase
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
BRITE hierarchy
Sysname
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)
Reaction(IUBMB)
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate [RN:R02305]
Reaction(KEGG)
Substrate
(2E,6E)-farnesyl diphosphate [CPD:C00448]
Product
pentalenene [CPD:C01841];
diphosphate [CPD:C00013]
Comment
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 1alpha hydrogen of pentalenene.
History
EC 4.2.3.7 created 1989 as EC 4.6.1.5, transferred 2000 to EC 4.2.3.7
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec00999  Biosynthesis of secondary metabolites - unclassified
ec01130  Biosynthesis of antibiotics
Orthology
K12250  pentalenene synthase
Genes
SMA: SAVERM_2998(ptlA)
SBH: SBI_09679
SCI: B446_29695
SCW: TU94_27405
SLE: sle_13160(sle_13160)
SSIA: A7J05_09240
Taxonomy
Reference
1  [PMID:6642060]
  Authors
Cane DE.
  Title
Cell-free studies of monoterpene and sesquiterpene biosynthesis.
  Journal
Biochem Soc Trans 11:510-5 (1983)
Reference
2
  Authors
Cane, D.E. and Tillman, A.M.
  Title
Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate.
  Journal
J Am Chem Soc 105:122-124 (1983)
Reference
3  [PMID:8180213]
  Authors
Cane DE, Sohng JK, Lamberson CR, Rudnicki SM, Wu Z, Lloyd MD, Oliver JS, Hubbard BR.
  Title
Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319.
  Journal
Biochemistry 33:5846-57 (1994)
  Sequence
[sbh:SBI_09679]
Reference
4  [PMID:1678531]
  Authors
Cane DE, Abell C, Harrison PH, Hubbard BR, Kane CT, Lattman R, Oliver JS, Weiner SW
  Title
Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions.
  Journal
Philos Trans R Soc Lond B Biol Sci 332:123-9 (1991)
DOI:10.1098/rstb.1991.0040
Reference
5  [PMID:9295272]
  Authors
Lesburg CA, Zhai G, Cane DE, Christianson DW
  Title
Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology.
  Journal
Science 277:1820-4 (1997)
DOI:10.1126/science.277.5333.1820
Reference
6  [PMID:22738258]
  Authors
Zu L, Xu M, Lodewyk MW, Cane DE, Peters RJ, Tantillo DJ
  Title
Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry.
  Journal
J Am Chem Soc 134:11369-71 (2012)
DOI:10.1021/ja3043245
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.7
IUBMB Enzyme Nomenclature: 4.2.3.7
ExPASy - ENZYME nomenclature database: 4.2.3.7
BRENDA, the Enzyme Database: 4.2.3.7
CAS: 90597-46-9

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