Information on EC 4.2.1.125 - dammarenediol II synthase

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The expected taxonomic range for this enzyme is: Apiineae

EC NUMBER
COMMENTARY hide
4.2.1.125
-
RECOMMENDED NAME
GeneOntology No.
dammarenediol II synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dammarenediol II = (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
ginsenosides biosynthesis
-
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Sesquiterpenoid and triterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(S)-squalene-2,3-epoxide hydro-lyase (dammarenediol-II forming)
The reaction occurs in the reverse direction.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene PqDS
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
-
close correlation of dammarenediol synthetase and saponin production in vitro
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
(3S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
(S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
-
S-isomer is the sole product, water addition to the dammarenyl cation intermediate is stereospecific
-
?
(S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol + hydroxydammarenone
show the reaction diagram
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-
-
-
?
additional information
?
-
-
LC-MS analysis of substrate and product amounts
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-
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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
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-((3-cholamidopropyl)dimethylammonio)-1-propanesulfonate
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i.e. CHAPS, 0.1%, 30% residual activity
deoxycholate
-
0.1%, 92% residual activity
n-octyl-beta-D-glucoside
-
0.1%, 58% residual activity
Triton X-100
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0.1%, 64% residual activity
Tween 20
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0.1%, 23% residual activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
methyl jasmonate
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up-regulation of enzyme expression
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
hairy root culture
Manually annotated by BRENDA team
-
higher expression compared with root, leaf and petiole
Manually annotated by BRENDA team
-
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
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higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
transmembrane enzyme
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strains Origami B (DE3) amd Rosetta (DE3) by nickel affinity chromatography
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recombinnat enzyme from Saccharomyces cerevisiae strain 31147 lipid particles, solubilization by Triton X-100
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, recombinant expression of functional His-tagged enzyme in Escherichia coli strains Origami B (DE3) amd Rosetta (DE3)
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expression in an engineered strain of Saccharomyces cerevisiae strain 31147 from vector pAUR123, the enzyme is contained in microsomes, lipid particles, and total yeast homogenate
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expression in Saccharomyces cerevisiae
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functional expression in Sacchaormyces cerevisiae
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gene PgDDS, functional expression in Nicotiana tabacum cv. Xanthi leaves using Agrobacterium strain GV3101, the heterologous expression confers resistance to Tobacco mosaic virus. Expression profile of PgDDS trangenic tobacco plants, overview. Production of dammarenediol-II in transgenic tobacco stimulates the expression of tobacco pathogenesis-related genes (PR1 and PR2) under both virus-untreated and -treated conditions
gene PqDS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, ectopic heterologous co-expression with cytochrome P450 gene PqD12H in Saccharomyces cerevisiae
recombinant expression in Nicotiana tabacum cv. Xanthi leaves using transfection via Agrobacterium tumefaciens strain LBA4404, accumulation of dammarenediol-II in transgenic tobacco plants occurred in an organ-specific manner in descending order: roots, stems, leaves, flower buds, and transgenic cell suspension line 14 exhibits a high amount, overview
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
induction by methyl jasmonate, overview
transcription increase of gene PqDS in the methyl jasmonate-induced hairy roots
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
the production of dammarenediol-II in a cell suspension culture of transgenic tobacco can be applied to the large-scale production of this compound and utilized as a source of pharmacologically active medicinal materials