Information on EC 4.2.3.11 - sabinene-hydrate synthase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
4.2.3.11
-
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RECOMMENDED NAME
GeneOntology No.
sabinene-hydrate synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = sabinene hydrate + diphosphate
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
P-O bond cleavage
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Monoterpenoid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
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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
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CAS REGISTRY NUMBER
COMMENTARY hide
117164-95-1
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Moench
-
-
Manually annotated by BRENDA team
Bentham Vogel
-
-
Manually annotated by BRENDA team
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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
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diphosphate
-
0.1 mM: 30% stimulation
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0027
(3R)-linalyl diphosphate
-
pH 7.0, 30°C
0.001
(3S)-linalyl diphosphate
-
pH 7.0, 30°C
0.0045
6,7-dihydrogeranyl diphosphate
-
pH 7.0, 30°C
0.0019
geranyl diphosphate
-
pH 7.0, 30°C
0.0105
neryl diphosphate
-
pH 7.0, 30°C
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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, 30°C
0.0003
(RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate
-
pH 7.0, 30°C
0.0042
6,7-dihydrogeranyl diphosphate
-
pH 7.0, 30°C
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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
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 8
-
50% of maximal activity at pH 6.3 and 8.0
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
-
gel filtration
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
complete inactivation after 20 min
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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
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli; expression in Escherichia coli
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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
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LINKS TO OTHER DATABASES (specific for EC-Number 4.2.3.11)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)