KEGG   ORTHOLOGY: K18686
Entry
K18686                      KO                                     
Symbol
cotB2
Name
cyclooctat-9-en-7-ol synthase [EC:4.2.3.146]
Pathway
map00997  Biosynthesis of various other secondary metabolites
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00921  Cyclooctatin biosynthesis, dimethylallyl-PP + isopentenyl-PP => cyclooctatin
Reaction
R10763  geranylgeranyl-diphosphate diphosphate-lyase (cyclooctat-9-en-7-ol-forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00997 Biosynthesis of various other secondary metabolites
    K18686  cotB2; cyclooctat-9-en-7-ol synthase
Enzymes [BR:ko01000]
 4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.146  cyclooctat-9-en-7-ol synthase
     K18686  cotB2; cyclooctat-9-en-7-ol synthase
Genes
SVL: Strvi_5779
SRC: M271_43275
SMAL: SMALA_0742
SSOI: I1A49_07300
SCI: B446_28660
SRN: A4G23_04517
SAUO: BV401_07560
SFB: CP974_24295
SANT: QR300_36895
SOV: QZH56_30185
AG: BAI44338(cotB2)
 » show all
Reference
  Authors
Kim SY, Zhao P, Igarashi M, Sawa R, Tomita T, Nishiyama M, Kuzuyama T
  Title
Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two p450 hydroxylases.
  Journal
Chem Biol 16:736-43 (2009)
DOI:10.1016/j.chembiol.2009.06.007
  Sequence
LinkDB

KEGG   ENZYME: 4.2.3.146
Entry
EC 4.2.3.146                Enzyme                                 
Name
cyclooctat-9-en-7-ol synthase;
cotB2
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
Sysname
geranylgeranyl-diphosphate diphosphate-lyase (cyclooctat-9-en-7-ol-forming)
Reaction(IUBMB)
geranylgeranyl diphosphate + H2O = cyclooctat-9-en-7-ol + diphosphate [RN:R10763]
Reaction(KEGG)
R10763
Substrate
geranylgeranyl diphosphate [CPD:C00353];
H2O [CPD:C00001]
Product
cyclooctat-9-en-7-ol [CPD:C20834];
diphosphate [CPD:C00013]
Comment
Requires Mg2+. Isolated from the bacterium Streptomyces melanosporofaciens, where it is part of the biosynthesis of cyclooctatin, a potent inhibitor of lysophospholipase.
History
EC 4.2.3.146 created 2014
Pathway
ec00997  Biosynthesis of various other secondary metabolites
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K18686  cyclooctat-9-en-7-ol synthase
Genes
SVLStrvi_5779
SRCM271_43275
SMALSMALA_0742
SSOII1A49_07300
SCIB446_28660
SRNA4G23_04517
SAUOBV401_07560
SFBCP974_24295
SANTQR300_36895
SOVQZH56_30185
SLUOPS467_06925
 » show all
Reference
1  [PMID:19635410]
  Authors
Kim SY, Zhao P, Igarashi M, Sawa R, Tomita T, Nishiyama M, Kuzuyama T
  Title
Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two p450 hydroxylases.
  Journal
Chem Biol 16:736-43 (2009)
DOI:10.1016/j.chembiol.2009.06.007
  Sequence
Reference
2  [PMID:24598929]
  Authors
Zhang X, Shang G, Gu L, Shen Y
  Title
Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) from Streptomyces sp. LZ35.
  Journal
Acta Crystallogr F Struct Biol Commun 70:366-9 (2014)
DOI:10.1107/S2053230X14003100
Reference
3  [PMID:24914964]
  Authors
Janke R, Gorner C, Hirte M, Bruck T, Loll B
  Title
The first structure of a bacterial diterpene cyclase: CotB2.
  Journal
Acta Crystallogr D Biol Crystallogr 70:1528-37 (2014)
DOI:10.1107/S1399004714005513
Reference
4  [PMID:25689152]
  Authors
Meguro A, Motoyoshi Y, Teramoto K, Ueda S, Totsuka Y, Ando Y, Tomita T, Kim SY, Kimura T, Igarashi M, Sawa R, Shinada T, Nishiyama M, Kuzuyama T
  Title
An unusual terpene cyclization mechanism involving a carbon-carbon bond rearrangement.
  Journal
Angew Chem Int Ed Engl 54:4353-6 (2015)
DOI:10.1002/anie.201411923
Reference
5  [PMID:28463490]
  Authors
Tomita T, Kim SY, Teramoto K, Meguro A, Ozaki T, Yoshida A, Motoyoshi Y, Mori N, Ishigami K, Watanabe H, Nishiyama M, Kuzuyama T
  Title
Structural Insights into the CotB2-Catalyzed Cyclization of Geranylgeranyl Diphosphate to the Diterpene Cyclooctat-9-en-7-ol.
  Journal
ACS Chem Biol 12:1621-1628 (2017)
DOI:10.1021/acschembio.7b00154
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.146
IUBMB Enzyme Nomenclature: 4.2.3.146
ExPASy - ENZYME nomenclature database: 4.2.3.146
BRENDA, the Enzyme Database: 4.2.3.146
LinkDB

KEGG   REACTION: R10763
Entry
R10763                      Reaction                               
Name
geranylgeranyl-diphosphate diphosphate-lyase (cyclooctat-9-en-7-ol-forming)
Definition
Geranylgeranyl diphosphate + H2O <=> Cyclooctat-9-en-7-ol + Diphosphate
Equation
Reaction class
RC03272  C00353_C20834
Enzyme
Pathway
rn00997  Biosynthesis of various other secondary metabolites
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00921  Cyclooctatin biosynthesis, dimethylallyl-PP + isopentenyl-PP => cyclooctatin
Brite
Enzymatic reactions [BR:br08201]
 4. Lyase reactions
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.146
     R10763  Geranylgeranyl diphosphate + H2O <=> Cyclooctat-9-en-7-ol + Diphosphate
Orthology
K18686  cyclooctat-9-en-7-ol synthase [EC:4.2.3.146]
Other DBs
RHEA: 41631
LinkDB

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