Information on EC 5.4.99.41 - lupeol synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
5.4.99.41
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RECOMMENDED NAME
GeneOntology No.
lupeol synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(3S)-2,3-epoxy-2,3-dihydrosqualene = lupeol
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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lupeol biosynthesis
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mangrove triterpenoid biosynthesis
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pentacyclic triterpene biosynthesis
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Sesquiterpenoid and triterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(3S)-2,3-epoxy-2,3-dihydrosqualene mutase (cyclizing, lupeol-forming)
Also forms some beta-amyrin. The recombinant enzyme from Arabidopsis thaliana [3] gives a 1:1 mixture of lupeol and lupan-3beta,20-diol with small amounts of beta-amyrin, germanicol, taraxasterol and psi-taraxasterol. See EC 4.2.1.128 (lupan-3beta,20-diol synthase).
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
Pentalinon andrieuxii
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(18E)-22,23-dihydro-20-oxa-oxidosqualene
3beta-hydroxy-22,23-24-25-26-27-hexanor-17beta-dammaran-20-one
show the reaction diagram
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the 20-oxa substitution has negligible effect on substrate binding and on the activation energies
sole product
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?
(3S)-2,3-oxidosqualene
lupeol
show the reaction diagram
(3S)-2,3-oxidosqualene
luteol
show the reaction diagram
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beta-amyrin is a minor product
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?
(3S)-oxidosqualene
lupeol
show the reaction diagram
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?
(3S,22S)-2,3:22,23-dioxidosqualene
(2R,4aR,6aS,6bS,10R,12aS,14aR,14bS)-2-(1-hydroxy-1-methylethyl)-4a,6a,6b,9,9,12a-hexamethylicosahydro-2H-phenanthro[1,2-h]chromen-10-ol + (3alpha,5xi,8alpha,9xi,10alpha,13aalpha,14beta,17xi,20R,24R)-20,24-epoxydammarane-3,25-diol + (3alpha,5xi,8alpha,9xi,10alpha,13alpha,14beta,17xi,24R)-20,24-epoxydammarane-3,25-diol
show the reaction diagram
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products 5_4_99.B3_11.8, 5_4_99.B3_11.9a and 5_4_99.B3_11.9b in ratio 3:4:2, almost complete consumption of substrate
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?
(S)-2,3-oxidosqualene
lupeol
show the reaction diagram
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?
2,3-oxidosqualene
lupeol
show the reaction diagram
2,3-oxidosqualene
lupeol + germanicol + beta-amyrin + taraxasterol + psi-taraxasterol + 3,20-dihydroxylupane
show the reaction diagram
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?
3-(omega-oxidogeranlygeranyl)indole
petromindole
show the reaction diagram
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substrate undergoes protonation, epoxide ring opening, and chair-chair bicyclization to cation. A Markovnikov intermediate is strongly favored, and its cyclization to indole forms the final product
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additional information
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Pentalinon andrieuxii
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the labeling profile of lupeol-3-(3'-hydroxy)-sterarate (procrim b) from a 13CO2 pulse/chase experiment using Pentalinon andrieuxii plants grown under quasi physiological conditions is reported. The 13C-pattern reveals the origin of the isopentyl diphosphate/demethylallyl diphosphate precursors, as well as important details on the cyclization processes occurring in the biosynthesis of lupeol-3-(3'-hydroxy)-sterarate
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2,3-oxidosqualene
lupeol
show the reaction diagram
Q2XPU7
lupeol is the main cuticular wax compound during early stages of hypocotyl development. Enzyme is responsible for formation of the cuticular lupeol and thus for the characteristic surface properties of Rhicinus communis stems
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
hypocotyl portion of stem, high activity during early development
Manually annotated by BRENDA team
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root nodule
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Sacchaormyces cerevisiae
expression in Saccharomyces cerevisae
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae lacking lanosterol and ergosterol synthase activities
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expression in Saccharomyces cerevisiae lacking lanosterol synthase activity
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
LUS gene expression is found to increase abruptly 10 h after Phomopsis induction; NaNO2 and L-arginine and NO donor sodium nitroprusside (SNP) are found to increase both NO production and LUS gene expression
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L256A
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mutation in region responsible for product differentiation. Mutant produces 3.8% beta-amyrin, 69.5% lupeol, 10% butyrospermol and 13.5% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
L256F
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mutation in region responsible for product differentiation. Mutant produces 9.8% beta-amyrin, 69.7% lupeol, 17.9% butyrospermol
L256H
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mutation in region responsible for product differentiation. Mutant produces 3.8% beta-amyrin, 69.5% lupeol, 10% butyrospermol and 13.5% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
L256W
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mutation in region responsible for product differentiation. Mutant produces 74.8% beta-amyrin, 6.9% lupeol, 9.9% butyrospermol and 8.4% germanicol
L256Y
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mutation in region responsible for product differentiation. Mutant produces 1.6% beta-amyrin, 54.8% lupeol, 22.7% butyrospermol and 18.7% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
Y258H
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mutation in region responsible for product differentiation. Mutant produces 43.6% lupeol, 6.2% butyrospermol and 42.4% of dammara-18(E),21-dien-3beta-ol, dammara-18(Z),21-dien-3beta-ol and dammara-18(28),21-dien-3beta-ol
yes
functional expression in Sacchaormyces cerevisiae results in production of lupeol
additional information