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
ec00902  Monoterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K07385  1,8-cineole synthase
Genes
ATH: AT3G25820(TPS-CIN) AT3G25830(TPS-CIN)
ALY: ARALYDRAFT_664366 ARALYDRAFT_904750 ARALYDRAFT_904756
CRB: 17886577
CSAT: 104710355 104710356 104710358 104779781 104790200 104790201 104790204
BRP: 103842433 103875347 103875348
BNA: 106349407 106349408 106349411 106382005 106425238 106425254 106425292
BOE: 106305939 106306158 106306160
THJ: 104805843 104816938
CPAP: 110819278
CIT: 102610882 102611160 102622591
MDM: 103417109
CMAX: 111470415
CMOS: 111434912
CPEP: 111777713
SLY: 101246974
SIND: 105175395
MUS: 103980879
 » show all
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 309:184-92 (1994)
DOI:10.1006/abbi.1994.1101
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 273:14891-9 (1998)
DOI:10.1074/jbc.273.24.14891
  Sequence
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 417:203-11 (2003)
DOI:10.1016/S0003-9861(03)00347-3
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 135:1956-66 (2004)
DOI:10.1104/pp.104.044388
  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 71:844-52 (2010)
DOI:10.1016/j.phytochem.2010.03.013
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.108
IUBMB Enzyme Nomenclature: 4.2.3.108
ExPASy - ENZYME nomenclature database: 4.2.3.108
BRENDA, the Enzyme Database: 4.2.3.108
CAS: 110637-19-9

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