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Information on EC 1.14.14.51 - (S)-limonene 6-monooxygenase
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EC Tree
1.14.14.51 (S)-limonene 6-monooxygenaseIUBMB Comments
A cytochrome P-450 (heme thiolate) enzyme. The enzyme participates in the biosynthesis of (-)-carvone, which is responsible for the aroma of spearmint.
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Word Map
- 1.14.14.51
- spearmint
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monoterpene
-
regiospecific
- peppermint
-
olefin
- carvone
- mentha
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trans-carveol
- limonene-3-hydroxylase
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regiochemistry
- hydroxylases
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geranyl
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p-menthane
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conversions
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perillyl
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facial
- carveol
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p450-catalyzed
- piperita
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allylic
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monoterpenoids
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stereochemistry
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enantiomers
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stereochemical
- fad
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complementarity
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
Synonyms
limonene-6-hydroxylase, limonene hydroxylase, (-)-(4s)-limonene-6-hydroxylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(-)-limonene 6-hydroxylase
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(-)-limonene 6-monooxygenase
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(-)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)
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EC 1.14.13.48
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formerly
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limonene hydroxylase
oxygenase, (-)-limonene 6-mono-
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
KEGG
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-
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SYSTEMATIC NAME
IUBMB Comments
(S)-limonene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
A cytochrome P-450 (heme thiolate) enzyme. The enzyme participates in the biosynthesis of (-)-carvone, which is responsible for the aroma of spearmint.
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CAS REGISTRY NUMBER
COMMENTARY
138066-93-0
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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
(-)-(4S)-limonene + NADPH + O2
(-)-trans-isopiperitenol + NADP+ + H2O
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mutant F363I
mutant F363I
?
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
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-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
4-methyl benzyl alcohol + NAD+
? + NADH
17.1% activity compared to perillyl alcohol
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-
?
carveol + NAD+
? + NADH
86% activity compared to perillyl alcohol
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-
?
cyclohexyl methanol + NAD+
cyclohexylaldehyde + NADH
15.8% activity compared to perillyl alcohol
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-
?
myrtenol + NAD+
myrtenal + NADH
4.0% activity compared to perillyl alcohol
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-
?
perillyl aldehyde + NADH
perillyl alcohol + NAD+
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-
-
r
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
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hydroxylation at 25% the rate of (-)-limonene
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?
(+)-limonene + NADPH + O2
(+)-cis-carveol + NADP+ + H2O
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radiation induced mutant 86% the rate of (-)-limonene
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?
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
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i.e. (+)-8,9-dihydrolimonene, hydroxylation at 30% the rate of (-)-limonene
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-
?
(+)-p-menth-1-ene + NADPH + O2
(+)-cis-carvotanacetol + NADP+ + H2O
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-
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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-
-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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-
?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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highly specific
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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highly specific
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?
(-)-(4S)-limonene + NADPH + O2
(-)-(4R,6S)-trans-carveol + NADP+ + H2O
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highly specific
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?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
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i.e. (-)-8,9-dihydrolimonene, hydroxylation at 74% the rate of (-)-limonene
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?
(-)-p-menth-1-ene + NADPH + O2
(-)-trans-carvotanacetol + NADP+ + H2O
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?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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convertion of (S)-limonene to cis- and trans-carveols in cells in 11% and 9% yields, respectively, after 6 h. The cells discriminate the (R) and (S) stereoisomers of the limonene and hydroxylate regioselectively at the 6-position of the (R) form
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?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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convertion of (S)-limonene to cis- and trans-carveols in cells in 11% and 9% yields, respectively, after 6 h. The cells discriminate the (R) and (S) stereoisomers of the limonene and hydroxylate regioselectively at the 6-position of the (R) form
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?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
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?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
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?
1-cyclohexene 1-methanol + NAD+
1-cyclohexen-1-carbaldehyde + NADH + H+
9.6% activity compared to perillyl alcohol
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?
1-cyclohexene 1-methanol + NAD+
1-cyclohexen-1-carbaldehyde + NADH + H+
9.6% activity compared to perillyl alcohol
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?
4-isopropyl benzyl alcohol + NAD+
4-isopropylbenzyl aldehyde + NADH
42.2% activity compared to perillyl alcohol
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?
4-isopropyl benzyl alcohol + NAD+
4-isopropylbenzyl aldehyde + NADH
42.2% activity compared to perillyl alcohol
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?
benzyl alcohol + NAD+
benzaldehyde + NADH
3.1% activity compared to perillyl alcohol
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?
benzyl alcohol + NAD+
benzaldehyde + NADH
3.1% activity compared to perillyl alcohol
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?
perillyl alcohol + NAD+
perillyl aldehyde + NADH
100% activity
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r
perillyl alcohol + NAD+
perillyl aldehyde + NADH
100% activity
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r
additional information
?
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(4R)-limonene leads to multiple products indicating allylic rearrangement
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?
additional information
?
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(4R)-limonene leads to multiple products indicating allylic rearrangement
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?
additional information
?
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no substrates: isolimonenes, terpinolene, alpha- or beta-phellandrene, alpha- or beta-terpinene, bicyclic monoterpenes: pinene, sabinene, alpha-thujene, p-cymene, cis- or trans-p-menthane, NADH can replace NADPH, but more slowly
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?
additional information
?
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(S)-limonene is hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also show the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. Biotransformation of (+)-limonene oxide produces (1S,2S,4R)-limonene-1,2-diol and (1S,4R)-limonene-1-ol-2-one in 32% and 16% yields, respectively, and (1R,2S,4R)-limonene oxide is recovered
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?
additional information
?
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(S)-limonene is hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also show the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. Biotransformation of (+)-limonene oxide produces (1S,2S,4R)-limonene-1,2-diol and (1S,4R)-limonene-1-ol-2-one in 32% and 16% yields, respectively, and (1R,2S,4R)-limonene oxide is recovered
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-
?
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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
(-)-limonene + NADPH + O2
(-)-trans-carveol + NADP+ + H2O
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone
-
-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
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convertion of (S)-limonene to cis- and trans-carveols in cells in 11% and 9% yields, respectively, after 6 h. The cells discriminate the (R) and (S) stereoisomers of the limonene and hydroxylate regioselectively at the 6-position of the (R) form
-
-
?
(S)-limonene + NADPH + H+ + O2
(-)-trans-carveol + NADP+ + H2O
-
convertion of (S)-limonene to cis- and trans-carveols in cells in 11% and 9% yields, respectively, after 6 h. The cells discriminate the (R) and (S) stereoisomers of the limonene and hydroxylate regioselectively at the 6-position of the (R) form
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-
?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
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-
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?
(S)-limonene + [reduced NADH-hemoprotein reductase] + O2
(-)-trans-carveol + [oxidized NADH-hemoprotein reductase] + H2O
-
-
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?
additional information
?
-
-
(S)-limonene is hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also show the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. Biotransformation of (+)-limonene oxide produces (1S,2S,4R)-limonene-1,2-diol and (1S,4R)-limonene-1-ol-2-one in 32% and 16% yields, respectively, and (1R,2S,4R)-limonene oxide is recovered
-
-
?
additional information
?
-
-
(S)-limonene is hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also show the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. Biotransformation of (+)-limonene oxide produces (1S,2S,4R)-limonene-1,2-diol and (1S,4R)-limonene-1-ol-2-one in 32% and 16% yields, respectively, and (1R,2S,4R)-limonene oxide is recovered
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
clotrimazole
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i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong
miconazole
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i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, strong
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5 - 10
about 40% activity at pH 5.5, about 75% activity at pH 6.5, about 90% activity at pH 7.0, 100% activity at 8.0, about 75% activity at pH 9.0, about 40% activity at pH 10.0
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 55
about 35% activity at 30°C, about 55% activity at 37°C, about 90% activity at 40°C, 100% activity at 45°C, about 75% activity at 50°C, about 30% activity at 55°C
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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
Show AA Sequence and Transmembrane Helices (522 entries)
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
57000
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
repetitive production of carveol from limonene was achieved using Ca2+ alginate-immobilized cyanobacterial cells
additional information
-
repetitive production of carveol from limonene was achieved using Ca2+ alginate-immobilized cyanobacterial cells
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
partial
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli. Systematic attempt to install the multistep pathway from isopentenyl diphosphate and dimethylallyl diphosphate to (-) carvone in Escherichia coli, limitations when using microbial hosts that are not otherwise enhanced for isoprenoid production
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