Information on EC 4.2.3.108 - 1,8-cineole synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
4.2.3.108
-
RECOMMENDED NAME
GeneOntology No.
1,8-cineole synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = 1,8-cineole + diphosphate
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Metabolic pathways
-
-
monoterpene biosynthesis
-
-
Monoterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (cyclizing, 1,8-cineole-forming)
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].
CAS REGISTRY NUMBER
COMMENTARY hide
110637-19-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
parents Lavandula angustifolia and Lavandula latifolia
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R)-linalyl diphosphate + H2O
? + diphosphate
show the reaction diagram
-
-
-
-
?
(3S)-linalyl diphosphate + H2O
? + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate
1,8-cineole + diphosphate
show the reaction diagram
geranyl diphosphate + H2O
1,8-cineole + diphosphate
show the reaction diagram
neryl diphosphate + H2O
1,8-cineole + diphosphate
show the reaction diagram
-
61% 1,8-cineole plus 18.5% sabinene, 8% alpha-phellandrene, 3.3% limonene, and 5.5% alpha-terpineol
-
?
neryl diphosphate + H2O
? + diphosphate
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-Fluorogeranyl diphosphate
-
competitive
2-Fluorolinalyl diphosphate
-
competitive
4-hydroxymercuribenzoate
-
inhibition is reversed by presence of cysteine
benzyl bromide
-
-
diethyl dicarbonate
-
inhibition is reversed by presence of hydroxylamine
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002
(3R)-linalyl diphosphate
-
pH 6.3, 30C
0.0042
(3S)-linalyl diphosphate
-
pH 6.3, 30C
0.00017 - 0.201
geranyl diphosphate
0.0045
neryl diphosphate
-
pH 6.3, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.096
geranyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.045 - 460
geranyl diphosphate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0032
2-Fluorogeranyl diphosphate
-
pH 6.3, 30C
0.0048
2-Fluorolinalyl diphosphate
-
pH 6.3, 30C
0.005
4-hydroxymercuribenzoate
-
pH 6.3, 30C
0.85
benzyl bromide
-
pH 6.3, 30C
0.3
diethyl dicarbonate
-
pH 6.3, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.6
-
isoelectric focusing
5.8
-
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
promoter activity is primarily found in the epidermis, cortex, and stele of mature primary and lateral roots, but not in the root meristem or the elongation zone
Manually annotated by BRENDA team
promoter activity is primarily found in the epidermis, cortex, and stele of mature primary and lateral roots, but not in the root meristem or the elongation zone
Manually annotated by BRENDA team
only expressed in sigma/style tissue and in petals
Manually annotated by BRENDA team
only expressed in sigma/style tissue and in petals
Manually annotated by BRENDA team
-
glandular trichome
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
-
gel filtration
72000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
x * 69400, calculated
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
homology-based protein model constructed on the 3-D crystal structure of the limonene synthase from Mentha spicata
to 1.95 A resolution, space group C2221. alpha-Helical protein comprised of 23 alpha-helices and eight 3/10 helices
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0
4 h, loss of about 20% of activity
22
2 h, loss of about 20% of activity
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Glycerol
-
10%, improves stability during the assay
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
daminozide significantly decreases gene expression of the monoterpene synthases sabinene synthase, borneol synthase, and 1,8-cineole synthase
expression of 1,8-cineole synthase and accumulation of its end product 1,8-cineole remain constant during the growth period until August and then decrease slightly
-
LiCINSmRNAlevels parallel the 1,8-cineole content in mature flowers and in developmental stages
regulation of gene expression by the circadian clock
the foliar application of gibberellic acid increases gene expression of the monoterpene synthases sabinene synthase, borneol synthase, and 1,8-cineole synthase. The amounts of two of the endproducts,1,8-cineole and camphor, are directly correlated with the levels of gene expression of the respective monoterpene synthases
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
N338A
products are 11.7% alpha-pinene, 33.1% sabinene, 33.2% beta-pinene, 16.9% myrcene, 5.1% limonene
N338C
products are 16.1% alpha-pinene, 41% sabinene, 32.1% beta-pinene, 4.7% myrcene, 6.1% limonene
N338I
products are 6.5% alpha-pinene, 48.3% sabinene, 8.2% myrcene, 37% limonene
N338I/A339T
products are 5.4% alpha-pinene, 62.1% sabinene, 6.4% myrcene, 26.1% limonene
N338I/A339T/G447S
products are 5.7% alpha-pinene, 59.6% sabinene, 5.0% myrcene, 29.7% limonene
N338I/A339T/G447S/I449P/P450T
products are 86.8% sabinene, 5.5% myrcene, 7.7% limonene
N338L
products are 4.7% alpha-pinene, 5.6% sabinene, 13.2% beta-pinene, 27.2% myrcene, 49.3% limonene
N338S
products are 9.8% alpha-pinene, 34.5% sabinene, 34.2% beta-pinene, 6.8% myrcene, 2.6% limonene, 5.6% alpha-cineole, 6.5% alpha-terpineol
N338V
products are 61.2% sabinene, 8.0% myrcene, 30.8% limonene
additional information