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Literature summary extracted from

  • Takahashi, S.; Yeo, Y.S.; Zhao, Y.; O'Maille, P.E.; Greenhagen, B.T.; Noel, J.P.; Coates, R.M.; Chappell, J.
    Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates (2007), J. Biol. Chem., 282, 31744-31754.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.151 expressed in WAT11 yeast strain Hyoscyamus muticus

Protein Variants

EC Number Protein Variants Comment Organism
1.14.14.151 A484I the mutation results in a catalytically compromised enzyme Hyoscyamus muticus
1.14.14.151 V366S the mutation dramatically reduces overall enzyme activity Hyoscyamus muticus
1.14.14.151 V480I/A484I mutant with improved catalytic efficiency Hyoscyamus muticus
1.14.14.151 V480S the mutation improves the kcat for the conversion of (-)-vetispiradiene to solavetivol about 2fold Hyoscyamus muticus
1.14.14.151 V482I mutant with improved catalytic efficiency Hyoscyamus muticus
1.14.14.151 V482I the mutation improves the kcat for the conversion of (-)-vetispiradiene to solavetivol about 2fold Hyoscyamus muticus
1.14.14.151 V482I/A484I the mutant possesses a 5fold improvement in its catalytic efficiency for nootkatol biosynthesis and a 10fold improvement for 2beta-hydroxy-epiaristolochene biosynthesis Hyoscyamus muticus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.14.151 0.0025
-
5-epiaristolochene mutant enzyme V480I/A484I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0033
-
5-epiaristolochene wild type enzyme, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0043
-
5-epiaristolochene mutant enzyme V482I/A484I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0062
-
(-)-vetispiradiene mutant enzyme V482I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0069
-
valencene mutant enzyme V482I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0074
-
valencene wild type enzyme, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0084
-
(-)-vetispiradiene mutant enzyme V480I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0121
-
valencene mutant enzyme V482I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.013
-
(-)-vetispiradiene mutant enzyme V482I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.014
-
(-)-vetispiradiene wild type enzyme, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0179
-
5-epiaristolochene mutant enzyme V482I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.0192
-
valencene mutant enzyme V480I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.14.151 microsome
-
Hyoscyamus muticus
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.151 additional information Hyoscyamus muticus HPO also catalyzes the equivalent regio-specific (C-2) hydroxylation of several eremophilane-type (decalin ring system) sesquiterpenes, such as with 5-epi-aristolochene ?
-
?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.151 Hyoscyamus muticus A6YIH8
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.151 (-)-vetispiradiene + [reduced NADPH-hemoprotein reductase] + O2
-
Hyoscyamus muticus solavetivol + [oxidized NADPH-hemoprotein reductase] + H2O solavetivol is also named premnaspirodien-2alpha-ol or (2S,4R,5S,7R)-spirovetiva-1(10),11(12)-dien-2-ol ?
1.14.14.151 4-epi-eremophilene + [reduced NADPH-hemoprotein reductase] + O2
-
Hyoscyamus muticus 4-epieremophilen-2beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.151 5-epiaristolochene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 substrate affinity for 5-epiaristolochene is 2-4times lower than that for valencene or (-)-premnaspirodiene, respectively. HPO catalyzes the conversion of 5-epiaristolochene to four mono-hydroxylated products with 2beta-hydroxy-epiaristolochene comprising greater than 80% of the reaction products, 1beta-hydroxy-epiaristolochene about 5%, 3alpha-hydroxy-epiaristolochene less than 2%, and an unknown mono-hydroxylated product of about 20% Hyoscyamus muticus 2beta-hydroxy-5-epiaristolochene + 1beta-hydroxy-5-epiaristolochene + 3alpha-hydroxy-5-epiaristolochene + 3 [oxidized NADPH-hemoprotein reductase] + 3 H2O
-
?
1.14.14.151 cedr-8-ene + [reduced NADPH-hemoprotein reductase] + O2
-
Hyoscyamus muticus cedr-8-en-15-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.151 additional information HPO also catalyzes the equivalent regio-specific (C-2) hydroxylation of several eremophilane-type (decalin ring system) sesquiterpenes, such as with 5-epi-aristolochene Hyoscyamus muticus ?
-
?
1.14.14.151 additional information the enzyme fails to convert nootkatol to nootkatone Hyoscyamus muticus ?
-
?
1.14.14.151 valencene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
-
Hyoscyamus muticus alpha-nootkatol + beta-nootkatol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.151 HPO
-
Hyoscyamus muticus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.14.14.151 0.2
-
5-epiaristolochene wild type enzyme, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 0.7
-
5-epiaristolochene mutant enzyme V480I/A484I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 1.4
-
5-epiaristolochene mutant enzyme V482I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 1.9
-
valencene wild type enzyme, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 2.1
-
(-)-vetispiradiene wild type enzyme, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 2.8
-
5-epiaristolochene mutant enzyme V482I/A484I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 3.8
-
(-)-vetispiradiene mutant enzyme V482I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 5.1
-
valencene mutant enzyme V482I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 5.7
-
valencene mutant enzyme V480I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 12.7
-
(-)-vetispiradiene mutant enzyme V480I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 15.9
-
valencene mutant enzyme V482I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 20.7
-
(-)-vetispiradiene mutant enzyme V482I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.14.14.151 60
-
5-epiaristolochene wild type enzyme, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 80
-
5-epiaristolochene mutant enzyme V482I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 150
-
(-)-vetispiradiene wild type enzyme, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 260
-
valencene wild type enzyme, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 280
-
5-epiaristolochene mutant enzyme V480I/A484I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 300
-
valencene mutant enzyme V480I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 610
-
(-)-vetispiradiene mutant enzyme V482I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 650
-
5-epiaristolochene mutant enzyme V482I/A484I, product is 2beta-hydroxy-epiaristolochene, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 740
-
valencene mutant enzyme V482I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 1310
-
valencene mutant enzyme V482I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 1510
-
(-)-vetispiradiene mutant enzyme V480I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus
1.14.14.151 1590
-
(-)-vetispiradiene mutant enzyme V482I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C Hyoscyamus muticus