Information on EC 4.2.3.11 - sabinene-hydrate synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.3.11
-
RECOMMENDED NAME
GeneOntology No.
sabinene-hydrate synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = sabinene hydrate + diphosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
P-O bond cleavage
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Metabolic pathways
-
-
Monoterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (cyclizing, sabinene-hydrate-forming)
Both cis- and trans- isomers of sabinene hydrate are formed. (3R)-Linalyl diphosphate is an intermediate in the reaction
CAS REGISTRY NUMBER
COMMENTARY hide
117164-95-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Moench
-
-
Manually annotated by BRENDA team
Bentham Vogel
-
-
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
(1S,2S,4R)-(E)-sabinene hydrate + diphosphate
show the reaction diagram
-
exclusive product of both isoforms Tps6 and Tps7
-
?
(3S)-linalyl diphosphate + H2O
(1R,2R,4S)-(E)-sabinene hydrate + diphosphate
show the reaction diagram
-
-
-
?
(3S)-linalyl diphosphate + H2O
(1S,2R,4S)-(Z)-sabinene hydrate + diphosphate
show the reaction diagram
-
no formation of the stereoisomer (1R,2S,4R)-(Z)-sabinene hydrate
-
?
2,3-methanogeranyl diphosphate + H2O
?
show the reaction diagram
-
at 1.5% of the rate of conversion of geranyl diphosphate to sabinene hydrate, noncyclizable substrate analog of geranyl diphosphate
-
-
?
6,7-dihydrogeranyl diphosphate + H2O
6,7-dihydromyrcene + ?
show the reaction diagram
-
noncyclizable substrate analog of geranyl diphosphate
-
-
?
geranyl diphosphate
sabinene hydrate + diphosphate
show the reaction diagram
geranyl diphosphate + H2O
(1S,2R,4S)-(Z)-sabinene hydrate + diphosphate
show the reaction diagram
-
the stereospecificity of the reaction is determined by the formation of the first intermediate, linalyl diphosphate. Products of isoform Tps6 are 60.4% (Z)-sabinene hydrate, 20.9% (E)-sabinene hydrate, 3.2% alpha-pinene, 2.6% myrcene plus traces of 12 more monoterpenes
-
?
geranyl diphosphate + H2O
(1S,2S,4R)-(E)-sabinene hydrate + diphosphate
show the reaction diagram
-
the stereospecificity of the reaction is determined by the formation of the first intermediate, linalyl diphosphate. Products of isoform Tps7 are 77.8% (1S,2S,4R)-(E)-sabinene hydrate, 6.3% limonene, 1.43% (Z)-sabinene hydrate plus traces of other monoterpenes
-
?
geranyl diphosphate + H2O
(E)-sabinene hydrate + diphosphate
show the reaction diagram
-
the stereospecificity of the reaction is determined by the formation of the first intermediate, linalyl diphosphate. Products of isoform Tps6 are 60.4% (Z)-sabinene hydrate, 20.9% (E)-sabinene hydrate, 3.2% alpha-pinene, 2.6% myrcene plus traces of 12 more monoterpenes
-
?
linalyl diphosphate
sabinene hydrate + diphosphate
show the reaction diagram
-
3R- and 3S-configuration
cis- and trans-sabinene hydrate
-
neryl diphosphate
sabinene hydrate + diphosphate
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(RS)-dimethyl-(4-methylcyclohex-3-en-1-yl)sulfonium iodide
-
-
(RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate
-
-
6,7-dihydrogeranyl diphosphate
-
competitive
diphosphate
-
0.5 mM: 80% inhibition
NaWO4
-
10 mM, 45% inhibition
NEM
-
IC50: 0.08 mM
NH4VO3
-
10 mM, 45% inhibition
PCMB
-
IC50: 0.02 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diphosphate
-
0.1 mM: 30% stimulation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0027
(3R)-linalyl diphosphate
-
pH 7.0, 30C
0.001
(3S)-linalyl diphosphate
-
pH 7.0, 30C
0.0045
6,7-dihydrogeranyl diphosphate
-
pH 7.0, 30C
0.0019
geranyl diphosphate
-
pH 7.0, 30C
0.0105
neryl diphosphate
-
pH 7.0, 30C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0028
(RS)-dimethyl-(4-methylcyclohex-3-en-1-yl)sulfonium iodide
-
pH 7.0, 30C
0.0003
(RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate
-
pH 7.0, 30C
0.0042
6,7-dihydrogeranyl diphosphate
-
pH 7.0, 30C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.08
NEM
Origanum majorana
-
IC50: 0.08 mM
0.02
PCMB
Origanum majorana
-
IC50: 0.02 mM
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 8
-
50% of maximal activity at pH 6.3 and 8.0
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
-
gel filtration
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
complete inactivation after 20 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
proteolytic degradation by 0.01 mg/ml trypsin, folowed by addition of soybean trypsin inhibitor: all cyclase activities are destroyed within 10 min, t1/2 is 3 min
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli; expression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
I346N
mutation to the corresponding residue in isoform Tps6. Mutation alters the stereospecificity to that of TPS6. (1S,2S,4R)-(E)-sabinene hydrate is still the main product of this mutant, but I346N also produces the (4S)-enantiomers of (E)-sabinene hydrate and (Z)-sabinene hydrate
N350I
mutation to the corresponding residue in isoform Tps7. Mutation alters the stereospecificity to that of TPS7, mutant produces only the (1S,2S,4R)-enantiomer of (E)-sabinene hydrate