Information on EC 5.4.99.8 - Cycloartenol synthase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
5.4.99.8
-
RECOMMENDED NAME
GeneOntology No.
Cycloartenol synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(3S)-2,3-epoxy-2,3-dihydrosqualene = cycloartenol
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
group transfer
-
-
intramolecular
-
isomerization
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
7-dehydroporiferasterol biosynthesis
-
avenacin biosynthesis
-
Biosynthesis of secondary metabolites
-
diploterol and cycloartenol biosynthesis
-
ergosterol biosynthesis II
-
mangrove triterpenoid biosynthesis
-
Metabolic pathways
-
plant sterol biosynthesis
-
Steroid biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
(S)-2,3-Epoxysqualene mutase (cyclizing, cycloartenol-forming)
-
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
2,3-Epoxysqualene cycloartenol-cyclase
-
-
-
-
2,3-epoxysqualene--cycloartenol cyclase
-
-
-
-
2,3-Epoxysqualene-cycloartenol cyclase
-
-
-
-
2,3-Oxidosqualene cycloartenol cyclase
-
-
-
-
2,3-Oxidosqualene-cycloartenol cyclase
-
-
-
-
2,3-Oxidosqualene:cycloartenol cyclase
-
-
-
-
CAS
A8UHA2
-
Cyclase, 2,3-oxidosqualene-cycloartenol
-
-
-
-
cycloartenol synthase
-
-
cycloartenol synthase
P38605
-
cycloartenol synthase
-
-
cycloartenol synthase
Q9SXV6
-
cycloartenol synthase 1
-
-
Oxidosqualene cyclase
-
-
PNX
O82139
-
CAS REGISTRY NUMBER
COMMENTARY
9075-25-6
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
coexistence of lanosterol synthase and cycloartenol synthase, comparison of sequences and discussion of specific roles of enzymes
-
-
Manually annotated by BRENDA team
cloning and characterization of triterpene synthases, epoxysqualene cyclase OSC5 is a cycloartenol synthase
-
-
Manually annotated by BRENDA team
Ochromonas malhamensis
-
-
-
Manually annotated by BRENDA team
fragment
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
-
antisense inhibition of cycloartenol synthase results in decreased phytosterol levels and enhanced ginsenoside levels
physiological function
-
cycloartenol synthase is responsible for the synthesis of cycloartenol providing skeletons for phytosterols
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
cycloartenol
show the reaction diagram
Q6Z2X6
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
Ochromonas malhamensis
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
Ochromonas malhamensis
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
A7BJ35, -
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
A7BJ36
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
O82139
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
P38605
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
-, Q9SXV6
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
A8R7G3, -
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
A8UHA2
-
-
-
?
oxidosqualene
cycloartenol
show the reaction diagram
-
-, sterol synthesis in plants
-
?
1-trans-1'-Norsqualene-2,3-epoxide
31-Norcycloartenol
show the reaction diagram
-
1-cis-1'-norsqualene-2,3-epoxide is not significantly cyclized
-
-
additional information
?
-
-
key enzyme in phytosterol biosynthesis
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-Epoxysqualene
Cycloartenol
show the reaction diagram
-
-
-
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
P38605
-
-
-
?
oxidosqualene
cycloartenol
show the reaction diagram
-
sterol synthesis in plants
-
?
(S)-2,3-oxidosqualene
cycloartenol
show the reaction diagram
-, Q9SXV6
-
-
-
?
additional information
?
-
-
key enzyme in phytosterol biosynthesis
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
KCl
Ochromonas malhamensis
-
enzyme is inactive in absence of KCl, stimulation at concentrations up to 0.35 M, at higher levels slight fall of activity
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2-Aza-2,3-dihydro-squalene-N-oxide
-
-
2-Aza-2,3-dihydrosqualene
-
-
2-Aza-2,3-dihydrosqualene
-
-
2-Aza-2,3-dihydrosqualene
-
-
2-hydroxyethyl jasmonate
A8UHA2
downregulation of gene expression at 200 mM, diethydithiocarbamate depresses the down-regulation of CAS gene expression by 2-hydroxyethyl jasmonate
3beta-(2-Diethylaminoethoxy)androstenone
-
-
8-Azadecalin
-
-
Carbenium ion intermediate analogue inhibitors
-
-
-
KCl
Ochromonas malhamensis
-
stimulation at concentrations up to 0.35 M, at higher levels slight fall of activity
KCl
-
activity sharply declines with increasing KCl concentration
methyl jasmonate
-
inhibits CaCYS transcription
N-Lauryl-N-dimethylamino-N-oxide
-
-
N-[(1,5,9)-Trimethyl-decyl]-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol
-
-
p-chloromercuribenzene sulfonic acid
-
-
p-hydroxymercuribenzoate
Ochromonas malhamensis
-
-
Sodium deoxycholate
Ochromonas malhamensis
-
stimulates at low concentrations, optimal activation at 0.1%. Inhibition at levels greater than 0.5%
Monocyclic 4-hydroxypiperidine
-
-
additional information
Q9SXV6
exogenous gibberellin A3, jasmonate and methyl jasmonate do not affect mRNA levels of cycloartenol synthase
-
additional information
-
addition of thidiazuron to methyl jasmonate treated smples, sustains mRNA expression
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2,3-Iminosqualene
Ochromonas malhamensis
-
-
dithiothreitol
Ochromonas malhamensis
-
stimulates
Sodium deoxycholate
Ochromonas malhamensis
-
inhibition at levels greater than 0.5%, stimulates at low concentrations, optimal activation at 0.1%
Sodium deoxycholate
-
the enzyme requires Triton X-100 or deoxycholate for maximal activity
Triton X-100
-
the enzyme requires Triton X-100 or deoxycholate for maximal activity
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.025
-
(S)-2,3-epoxysqualene
-
-
0.05
-
(S)-2,3-epoxysqualene
-
-
0.1
-
(S)-2,3-epoxysqualene
Ochromonas malhamensis
-
-
0.125
-
(S)-2,3-epoxysqualene
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.00019
-
Ochromonas malhamensis
-
-
additional information
-
-
-
additional information
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.5
7.5
-
-
6.5
7.5
-
-
7
7.3
Ochromonas malhamensis
-
-
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
Ochromonas malhamensis
-
30 min incubation
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
81000
-
-
calculated from nucleotide sequence
86300
-
-
calculated from amino acid sequence
100000
-
-
HPLC gel filtration
110000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
-
2 * 55000, SDS-PAGE
dimer
-
2 * 55000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-
Ochromonas malhamensis
-
partial
Ochromonas malhamensis
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli and in the yeast mutant GIL77
A8R7G3, -
expression in Escherichia coli
-
expression in Saccharomyces cerevisiae
-
expression in yeast
-
mutants are expressed in Saccharomyces cerevisiae strain LHY4
P38605
sequence comparisons of lanosterol synthases and cycloartenol synthases from several organisms
-
expression in DH5-alpha Escherichia coli competent cells
-
expression in Saccharomyces cerevisiae
-
expressed in Saccharomyces cerevisiae mutant GIL77 cells
-
expression in Saccharomyces cerevisiae
A7BJ36
gene is present in single copy. Expression of enzyme in Saccharomyces cerevisiae
-
expression in yeast
-
expression in Saccharomyces cerevisiae
A7BJ35, -
expression in Sacchaormyces cerevisiae
Q2XPU6, -
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
the cycloartenol synthase gene in hairy root cultures elicited by 0.1 mM methyl jasmonate treatment decreases slightly
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
H477N
-
mutated enzyme produces lanosterol instead of cycloartenol
H477N
-
produces 88% lanosterol and 12% parkeol
H477N/I481V
-
produces 99% lanosterol and 1% parkeol
H477Q
-
mutated enzyme produces parkeol instead of cycloartenol
H477Q
-
produces 22% lanosterol, 73% parkeol, and 5% 9-beta-delta-7-lanosterol
H477Q/I481V
-
produces 94% lanosterol and 6% parkeol
I481A
-
production of lanosterol, cycloartenol, parkeol, acilleol A and camelliol C
I481F
-
inactive
I481G
-
production of lanosterol, cycloartenol, parkeol, acilleol A and camelliol C
I481L
-
production of cycloartenol and parkeol
I481V
-
produces 54% cycloartenol, 25% lanosterol, and 21% parkeol
Y410T
-
produces 65% lanosterol, 2% parkeol, and 33% 9-beta-delta-7-lanosterol
Y410T/H477N/I481V
-
produces 78% lanosterol and 22% 9-beta-delta-7-lanosterol
Y410T/H477Q/I481V
-
produces 78% lanosterol and 22% 9-beta-delta-7-lanosterol
Y410T/I481V
-
mutated enzyme produces lanosterol instead of cycloartenol
Y410T/I481V
-
produces 78% lanosterol, less than 1% parkeol, and 22% 9-beta-delta-7-lanosterol
Y532H
-
mutated enzyme produces a mixture of parkeol, achilleol and lanosterol instead of cycloartenol
additional information
-
mutation N478H/V482I in lanosterol synthase is a change of amino acids crucial for lanosterol specificity to the cycloartenol synthase type. Mutant produces 4% lanosterol, 83% parkeol, and 13% cycloartenol from substrate (S)-2,3-epoxysqualene, while wild-type lanosterol synthase produces only lanosterol