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EC Tree
IUBMB Comments Both cis- and trans- isomers of sabinene hydrate are formed. (3R)-Linalyl diphosphate is an intermediate in the reaction
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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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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sabinene-hydrate synthase
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geranyl diphosphate + H2O = sabinene hydrate + diphosphate
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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P-O bond cleavage
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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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(3R)-linalyl diphosphate + H2O
(1S,2S,4R)-(E)-sabinene hydrate + diphosphate
(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
sabinene hydrate + diphosphate
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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geranyl diphosphate + H2O
cis-sabinene hydrate + diphosphate
linalyl diphosphate
sabinene hydrate + diphosphate
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3R- and 3S-configuration
cis- and trans-sabinene hydrate
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neryl diphosphate
sabinene hydrate + diphosphate
(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
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geranyl diphosphate
sabinene hydrate + diphosphate
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both cis- and trans-isomers of sabinene hydrate are formed
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geranyl diphosphate
sabinene hydrate + diphosphate
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both cis- and trans-isomers of sabinene hydrate are formed
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geranyl diphosphate
sabinene hydrate + diphosphate
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the ratio of (+)cis-sabinene hydrate to (+)-trans-sabinene hydrate is not constant
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geranyl diphosphate + H2O
cis-sabinene hydrate + diphosphate
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geranyl diphosphate + H2O
cis-sabinene hydrate + diphosphate
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neryl diphosphate
sabinene hydrate + diphosphate
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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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geranyl diphosphate + H2O
cis-sabinene hydrate + diphosphate
geranyl diphosphate + H2O
cis-sabinene hydrate + diphosphate
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?
geranyl diphosphate + H2O
cis-sabinene hydrate + diphosphate
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?
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Mg2+
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absolute requirement for divalent cation in the reaction with 6,7-dihydrogeranyl diphosphate, preference for Mn2+ over Mg2+
Mg2+
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Mg2+ or Mn2+ required, Km: 2.4 mM
Mn2+
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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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Mn2+ or Mg2+ required, Km: 0.3 mM
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(RS)-dimethyl-(4-methylcyclohex-3-en-1-yl)sulfonium iodide
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(RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate
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6,7-dihydrogeranyl diphosphate
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competitive
diphosphate
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0.5 mM: 80% inhibition
NaWO4
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10 mM, 45% inhibition
NH4VO3
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10 mM, 45% inhibition
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diphosphate
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0.1 mM: 30% stimulation
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0.0027
(3R)-linalyl diphosphate
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pH 7.0, 30°C
0.001
(3S)-linalyl diphosphate
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pH 7.0, 30°C
0.0045
6,7-dihydrogeranyl diphosphate
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pH 7.0, 30°C
0.0019
geranyl diphosphate
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pH 7.0, 30°C
0.0105
neryl diphosphate
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pH 7.0, 30°C
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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
0.0042
6,7-dihydrogeranyl diphosphate
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pH 7.0, 30°C
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0.08
NEM
Origanum majorana
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IC50: 0.08 mM
0.02
PCMB
Origanum majorana
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IC50: 0.02 mM
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6.3 - 8
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50% of maximal activity at pH 6.3 and 8.0
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brenda
Moench
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Bentham Vogel
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Moench
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isoform Tps6
UniProt
brenda
isoform Tps7
UniProt
brenda
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L0HB77_THYVU
597
0
69225
TrEMBL
Chloroplast (Reliability: 1 )
A0A151UEB1_CAJCA
68
0
7886
TrEMBL
other Location (Reliability: 5 )
A0A151QW72_CAJCA
253
0
29644
TrEMBL
other Location (Reliability: 2 )
L0HAM7_THYVU
603
0
70062
TrEMBL
Chloroplast (Reliability: 1 )
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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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45
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complete inactivation after 20 min
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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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expression in Escherichia coli
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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.
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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.
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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.
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546-555
2018
Origanum majorana, Origanum vulgare
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brenda
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4.2.3.11 sabinene-hydrate synthase
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