Literature summary for 1.14.14.151 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.

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Cloned(Commentary)

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

Protein Variants

Protein Variants	Comment	Organism
A484I	the mutation results in a catalytically compromised enzyme	Hyoscyamus muticus
V366S	the mutation dramatically reduces overall enzyme activity	Hyoscyamus muticus
V480I/A484I	mutant with improved catalytic efficiency	Hyoscyamus muticus
V480S	the mutation improves the kcat for the conversion of (-)-vetispiradiene to solavetivol about 2fold	Hyoscyamus muticus
V482I	mutant with improved catalytic efficiency	Hyoscyamus muticus
V482I	the mutation improves the kcat for the conversion of (-)-vetispiradiene to solavetivol about 2fold	Hyoscyamus muticus
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]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
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
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
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
0.0062	-	(-)-vetispiradiene	mutant enzyme V482I, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
0.0069	-	valencene	mutant enzyme V482I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
0.0074	-	valencene	wild type enzyme, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
0.0084	-	(-)-vetispiradiene	mutant enzyme V480I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
0.0121	-	valencene	mutant enzyme V482I/A484I, product is beta-nootkatol, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
0.013	-	(-)-vetispiradiene	mutant enzyme V482I/A484I, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
0.014	-	(-)-vetispiradiene	wild type enzyme, in 100 mM Tris-HCl, pH 7.5, at 30°C	Hyoscyamus muticus
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
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

Localization	Comment	Organism	GeneOntology No.	Textmining
microsome	-	Hyoscyamus muticus	-	-

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
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

Organism	UniProt	Comment	Textmining
Hyoscyamus muticus	A6YIH8	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
(-)-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	?
4-epi-eremophilene + [reduced NADPH-hemoprotein reductase] + O2	-	Hyoscyamus muticus	4-epieremophilen-2beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O	-	?
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	-	?
cedr-8-ene + [reduced NADPH-hemoprotein reductase] + O2	-	Hyoscyamus muticus	cedr-8-en-15-ol + [oxidized NADPH-hemoprotein reductase] + H2O	-	?
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	?	-	?
additional information	the enzyme fails to convert nootkatol to nootkatone	Hyoscyamus muticus	?	-	?
valencene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2	-	Hyoscyamus muticus	alpha-nootkatol + beta-nootkatol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O	-	?

Synonyms

Synonyms	Comment	Organism
HPO	-	Hyoscyamus muticus

Turnover Number [1/s]

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

kcat/KM [mM/s]

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

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Release 2023.1 (January 2023)