KEGG   ENZYME: 4.2.3.108Help
Entry
EC 4.2.3.108                Enzyme                                 

Name
1,8-cineole synthase;
1,8-cineole cyclase;
geranyl pyrophoshate:1,8-cineole cyclase;
1,8-cineole synthetase
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
BRITE hierarchy
Sysname
geranyl-diphosphate diphosphate-lyase (cyclizing, 1,8-cineole-forming)
Reaction(IUBMB)
geranyl diphosphate + H2O = 1,8-cineole + diphosphate [RN:R09964]
Reaction(KEGG)
R09964;
(other) R06421 R06422
Show
Substrate
geranyl diphosphate [CPD:C00341];
H2O [CPD:C00001]
Product
1,8-cineole [CPD:C09844];
diphosphate [CPD:C00013]
Comment
Requires Mn2+ or Zn2+. Mg2+ is less effective than either. 1,8-Cineole is the main product from the enzyme with just traces of other monoterpenoids. The oxygen atom is derived from water. The reaction proceeds via linalyl diphosphate and alpha-terpineol, the stereochemistry of both depends on the organism. However neither intermediate can substitute for geranyl diphosphate. The reaction in Salvia officinalis (sage) proceeds via (-)-(3R)-linalyl diphosphate [1-3] while that in Arabidopsis (rock cress) proceeds via (+)-(3S)-linalyl diphosphate [4].
History
EC 4.2.3.108 created 2012
Pathway
Monoterpenoid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K07385  
1,8-cineole synthase
Genes
ATH: 
AT3G25820(TPS-CIN) AT3G25830(TPS-CIN)
ALY: 
CRB: 
Taxonomy
Reference
1  [PMID:8117108]
  Authors
Croteau R, Alonso WR, Koepp AE, Johnson MA
  Title
Biosynthesis of monoterpenes: partial purification, characterization, and mechanism of action of 1,8-cineole synthase.
  Journal
Arch. Biochem. Biophys. 309 (1994) 184-92.
Reference
2  [PMID:9614092]
  Authors
Wise ML, Savage TJ, Katahira E, Croteau R.
  Title
Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase.
  Journal
J. Biol. Chem. 273 (1998) 14891-9.
  Organism
Salvia officinalis
  Sequence
[up:O81191]
Reference
3  [PMID:12941302]
  Authors
Peters RJ, Croteau RB
  Title
Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases.
  Journal
Arch. Biochem. Biophys. 417 (2003) 203-11.
Reference
4  [PMID:15299125]
  Authors
Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D.
  Title
Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole.
  Journal
Plant. Physiol. 135 (2004) 1956-66.
  Organism
Arabidopsis thaliana
  Sequence
[ath:AT3G25830]
Reference
5  [PMID:20399476]
  Authors
Keszei A, Brubaker CL, Carter R, Kollner T, Degenhardt J, Foley WJ
  Title
Functional and evolutionary relationships between terpene synthases from Australian Myrtaceae.
  Journal
Phytochemistry. 71 (2010) 844-52.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
110637-19-9

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