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Information on EC 4.2.3.11 - sabinene-hydrate synthase
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4.2.3.11 sabinene-hydrate synthaseIUBMB Comments
Both cis- and trans- isomers of sabinene hydrate are formed. (3R)-Linalyl diphosphate is an intermediate in the reaction
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The enzyme appears in viruses and cellular organisms
Synonyms
cyclase, sabinene hydrate, EC 4.6.1.9, sabinene hydrate cyclase, sabinene-hydrate synthase, TPS6, Tps7, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
cyclase, sabinene hydrate
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EC 4.6.1.9
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formerly
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sabinene hydrate cyclase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = sabinene hydrate + diphosphate
both cis- and trans-isomers of sabinene hydrate are formed. (3R)-Linalyl diphosphate is an intermediate in the reaction, mechanism and stereochemistry
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geranyl diphosphate + H2O = sabinene hydrate + diphosphate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
P-O bond cleavage
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PATHWAY SOURCE
PATHWAYS
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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
117164-95-1
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3S)-linalyl diphosphate
(1R,2R,4S)-(E)-sabinene hydrate + diphosphate
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-
-
-
?
(3S)-linalyl diphosphate + H2O
(1R,2R,4S)-(E)-sabinene hydrate + diphosphate
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-
-
?
(3S)-linalyl diphosphate + H2O
(1S,2R,4S)-(Z)-sabinene hydrate + diphosphate
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no formation of the stereoisomer (1R,2S,4R)-(Z)-sabinene hydrate
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?
2,3-methanogeranyl diphosphate + H2O
?
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at 1.5% of the rate of conversion of geranyl diphosphate to sabinene hydrate, noncyclizable substrate analog of geranyl diphosphate
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?
6,7-dihydrogeranyl diphosphate + H2O
6,7-dihydromyrcene + ?
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noncyclizable substrate analog of geranyl diphosphate
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-
?
geranyl diphosphate + H2O
(1S,2R,4S)-(Z)-sabinene hydrate + diphosphate
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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
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?
geranyl diphosphate + H2O
(1S,2S,4R)-(E)-sabinene hydrate + diphosphate
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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
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?
geranyl diphosphate + H2O
(E)-sabinene hydrate + diphosphate
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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
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?
linalyl diphosphate
sabinene hydrate + diphosphate
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3R- and 3S-configuration
cis- and trans-sabinene hydrate
?
(3R)-linalyl diphosphate + H2O
(1S,2S,4R)-(E)-sabinene hydrate + diphosphate
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?
(3R)-linalyl diphosphate + H2O
(1S,2S,4R)-(E)-sabinene hydrate + diphosphate
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exclusive product of both isoforms Tps6 and Tps7
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?
geranyl diphosphate
sabinene hydrate + diphosphate
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no free intermediate detectable in the conversion of geranyl diphosphate to sabinene hydrate
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geranyl diphosphate
sabinene hydrate + diphosphate
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the configuration at c1 of geranyl diphosphate is retained in the enzymatic conversion to (+)-cis and (+)-trans-sabinene hydrate
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geranyl diphosphate
sabinene hydrate + diphosphate
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constant ratio of (+)cis-sabinene hydrate to (+)-trans-sabinene hydrate is 20:1
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geranyl diphosphate
sabinene hydrate + diphosphate
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both cis- and trans-isomers of sabinene hydrate are formed
?
geranyl diphosphate
sabinene hydrate + diphosphate
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both cis- and trans-isomers of sabinene hydrate are formed
?
geranyl diphosphate
sabinene hydrate + diphosphate
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both cis- and trans-isomers of sabinene hydrate are formed
?
geranyl diphosphate
sabinene hydrate + diphosphate
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the ratio of (+)cis-sabinene hydrate to (+)-trans-sabinene hydrate is not constant
?
neryl diphosphate
sabinene hydrate + diphosphate
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cis- and trans-sabinene hydrate
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neryl diphosphate
sabinene hydrate + diphosphate
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cis- and trans-sabinene hydrate
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
Mg2+
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absolute requirement for divalent cation in the reaction with 6,7-dihydrogeranyl diphosphate, preference for Mn2+ over Mg2+
Mn2+
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absolute requirement for divalent cation in the reaction with 6,7-dihydrogeranyl diphosphate, preference for Mn2+ over Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0028
(RS)-dimethyl-(4-methylcyclohex-3-en-1-yl)sulfonium iodide
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pH 7.0, 30°C
0.0003
(RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate
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pH 7.0, 30°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A151QW72_CAJCA
253
0
29644
TrEMBL
other Location (Reliability: 2)
A0A151UEB1_CAJCA
68
0
7886
TrEMBL
other Location (Reliability: 5)
L0HAM7_THYVU
603
0
70062
TrEMBL
Chloroplast (Reliability: 1)
L0HB77_THYVU
597
0
69225
TrEMBL
Chloroplast (Reliability: 1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
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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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hallahan, T.W.; Croteau, R.
Monoterpene biosynthesis: mechanism and stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (+)-cis- and (+)-trans-sabinene hydrate
Arch. Biochem. Biophys.
269
313-326
1989
Origanum majorana
brenda
Hallahan, T.W.; Croteau, R.
Monoterpene biosynthesis: demonstration of a geranyl pyrophosphate:sabinene hydrate cyclase in soluble enzyme preparations from sweet marjoram (Majorana hortensis)
Arch. Biochem. Biophys.
264
618-631
1988
Origanum majorana, Origanum majorana Moench
brenda
Novak, J.; Bitsch, C.; Langbehn, J.; Pank, F.; Skoula, M.; Gotsiou, Y.; Franz, C.M.
Ratios of cis- and trans-sabinene sydrate in Origanum majorana L. and Origanum microphyllum (Bentham) Vogel
Biochem. Syst. Ecol.
28
697-704
2000
Origanum majorana, Origanum microphyllum
brenda
Keszei, A.; Hassan, Y.; Foley, W.J.
A Biochemical Interpretation of Terpene Chemotypes in Melaleuca alternifolia
J. Chem. Ecol.
36
652-661
2010
Melaleuca alternifolia
brenda
Krause, S.; Köllner, T.; Asbach, J.; Degenhardt, J.
Stereochemical mechanism of two sabinene hydrate synthases forming antipodal monoterpenes in thyme (Thymus vulgaris)
Arch. Biochem. Biophys.
529
112-121
2013
Thymus vulgaris (L0HAM7), Thymus vulgaris (L0HB77)
brenda
Jan, S.; Mir, J.; Shafi, W.; Faktoo, S.; Singh, D.; Wijaya, L.; Alyemeni, M.; Ahmad, P.
Divergence in tissue-specific expression patterns of genes associated with the terpeniod biosynthesis in two oregano species Origanum vulgare L., and Origanum majorana
Indust. Crops Prod.
123
546-555
2018
Origanum majorana, Origanum vulgare
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brenda
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