Information on EC 1.14.13.201 - beta-amyrin 28-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.201
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RECOMMENDED NAME
GeneOntology No.
beta-amyrin 28-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
beta-amyrin + 3 O2 + 3 NADPH + 3 H+ = oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
beta-amyrin + O2 + NADPH + H+ = erythrodiol + NADP+ + H2O
show the reaction diagram
erythrodiol + O2 + NADPH + H+ = oleanolic aldehyde + NADP+ + 2 H2O
show the reaction diagram
oleanolic aldehyde + O2 + NADPH + H+ = oleanolate + NADP+ + H2O
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ginsenosides biosynthesis
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ginsenoside metabolism
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SYSTEMATIC NAME
IUBMB Comments
beta-amyrin,NADPH:oxygen oxidoreductase (28-hydroxylating)
The enzyme, found in plants, is involved in the biosynthesis of oleanane-type triterpenoids, such as ginsenoside Ro. The enzyme from Medicago trunculata (CYP716A12) can also convert alpha-amyrin and lupeol to ursolic acid and betulinic acid, respectively.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in the biosynthesis of oleanane-type triterpenoids, such as ginsenoside Ro
physiological function
enzyme is responsible for an early step in the saponin biosynthetic pathway. Mutants in CYP716A12 are unable to produce hemolytic saponins and only synthetize soyasaponins. CYP716A12 catalyzes the oxidation of beta-amyrin and erythrodiol at the C-28 position, yielding oleanolic acid
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
alpha-amyrin + 3 O2 + 3 NADPH + 3 H+
ursolate + 3 NADP+ + 4 H2O
show the reaction diagram
beta-amyrin + 3 NADPH + 3 H+ + 3 O2
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
overall reaction
CYP716A12 mainly catalyzes the sequential three-step oxidation at the C-28 position necessary to transform beta-amyrin into oleanolic acid
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?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
beta-amyrin + O2 + NADPH + H+
erythrodiol + NADP+ + H2O
show the reaction diagram
erythrodiol + NADPH + H+ + O2
oleanolic aldehyde + NADP+ + 2 H2O
show the reaction diagram
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-
-
?
erythrodiol + O2 + NADPH + H+
oleanolic aldehyde + NADP+ + 2 H2O
show the reaction diagram
lupeol + 3 O2 + 3 NADPH + 3 H+
betulinate + 3 NADP+ + 4 H2O
show the reaction diagram
oleanolic aldehyde + O2 + NADPH + H+
oleanolate + NADP+ + H2O
show the reaction diagram
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
alpha-amyrin + 3 O2 + 3 NADPH + 3 H+
ursolate + 3 NADP+ + 4 H2O
show the reaction diagram
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
lupeol + 3 O2 + 3 NADPH + 3 H+
betulinate + 3 NADP+ + 4 H2O
show the reaction diagram
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
highest expression of the gene
Manually annotated by BRENDA team
significant increase in expression is observed in the reproductive stages, with a maximum expression at flowering
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
coexpression of PNY1 and CYP716A52v2 in yeast. Transgenic Panax ginseng plants constitutively overexpressing CYP716A52v2 and expressing a CYP716A52v2-RNAi are generated using Agrobacterium tumefaciens mediated genetic transformation; expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae
heterologous expression in Spodoptera frugiperda 9 insect cells and transgenic yeast
heterologous expression in Spodoptera frugiperda 9 insect cells and transgenic yeast; heterologous expression in Spodoptera frugiperda 9 insect cells and transgenic yeast
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CYP716A52v2 mRNA does not respond to methyl jasmonate treatment during the entire culture period