KEGG   ENZYME: 4.2.3.7
Entry
EC 4.2.3.7                  Enzyme                                 
Name
pentalenene synthase;
pentalenene synthetase
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
Sysname
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)
Reaction(IUBMB)
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate [RN:R02305]
Reaction(KEGG)
R02305
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
ec00998  Biosynthesis of various antibiotics
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12250  pentalenene synthase
Genes
MFBMFUL124B02_01475 MFUL124B02_01480
PTRIKDC22_17270
NYALTV02_15165
SMASAVERM_2998(ptlA)
SBHSBI_09679
SCIB446_29695
SCWTU94_27405
SLEsle_13160(sle_13160)
SSIAA7J05_09240
SRKFGW37_27330
SVRCP971_04990
SCINCP977_32300
SPLACP981_00105
SHUNDWB77_06666(ptlA)
SHARHUT13_06550
SPEUCGZ69_00970
SGJIAG43_11500 IAG43_27155
SHKJ2N69_35805
 » show all
Reference
1  [PMID:6642060]
  Authors
Cane DE.
  Title
Cell-free studies of monoterpene and sesquiterpene biosynthesis.
  Journal
Biochem Soc Trans 11:510-5 (1983)
DOI:10.1042/bst0110510
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)
DOI:10.1021/bi00185a024
  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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