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
4.2.1.125
-
RECOMMENDED NAME
GeneOntology No.
dammarenediol II synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
dammarenediol II = (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
show the reaction diagram
-
-
-
-
dammarenediol II = (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
show the reaction diagram
cyclization initiated by protonation at the oxirane ring proceeds to form tetracycles. The resulting dammarenyl cation is trapped by stereospecific addition of water at C20 without further rearrangement
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PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
ginsenosides biosynthesis
-
Sesquiterpenoid and triterpenoid biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
(S)-squalene-2,3-epoxide hydro-lyase (dammarenediol-II forming)
The reaction occurs in the reverse direction.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dammarenediol synthase
Q75W18
-
dammarenediol-II synthase
Q08IT1
-
PNA
Q08IT1
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
-
Q75W18
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
-
Centella asiatica hairy roots overexpressing ginseng farnesyl diphosphate synthase show higher levels of dammarenediol synthase and cycloartenol synthase mRNA when compared with the controls. No differences are detected in expression of the squalene synthase gene. The upregulation of dammarenediol synthase transcripts suggests that FPS may result in alterations in triterpene biosynthesis capacity. Squalene contents in the T17, T24, and T27 lines increase to 1.1-, 1.3- and 1.5fold those in the controls, respectively. The total sterol contents in the T24 line are approximately three times higher than those of the controls
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
-
-
the accumulated product was confirmed as dammarenediol
-
?
(3S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
-
substrate is folded in a pre-chair-chair-chair conformation
-
-
?
(S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
Q08IT1
-
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
Q75W18
-
-
-
?
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
3-((3-cholamidopropyl)dimethylammonio)-1-propanesulfonate
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
methyl jasmonate
Q75W18
up-regulation of enzyme expression
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
Q08IT1
hairy root culture
Manually annotated by BRENDA team
Q75W18
higher expression compared with root, leaf and petiole
Manually annotated by BRENDA team
Q75W18
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
Q75W18
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
-
hairy root
Manually annotated by BRENDA team
Q08IT1
hairy root culture
Manually annotated by BRENDA team
Q75W18
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
exclusive localization
-
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q08IT1
x * 88300, calculated
?
Q75W18
x * 88400, calculated
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Saccharomyces cerevisiae
-
functional expression in Sacchaormyces cerevisiae
Q08IT1
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
functionally expressed in the lanosterol synthase-deficient yeast mutant erg7
additional information
Q75W18
expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase results in production of dammarenediol and hydroxydammarenone. Silencing of gene expression by RNAi leads to a reduction of ginsenoide production to 84.5% in roots