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
LITERATURE
(3S)-2,3-epoxy-2,3-dihydrosqualene = cycloartenol
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
group transfer
-
-
intramolecular
-
isomerization
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
7-dehydroporiferasterol biosynthesis
-
-
avenacin biosynthesis, initial reactions
-
-
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
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
-
-
OSC/CS
D6R1X1
-
OSC/CS
Withania somnifera WS-Y-08
D6R1X1
-
-
Oxidosqualene cyclase
-
-
PNX
O82139
-
CAS REGISTRY NUMBER
COMMENTARY
9075-25-6
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
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
Withania somnifera WS-Y-08
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
D6R1X1
the enzyme belongs to the oxidosqualene cyclase OSC superfamily of enzymes
evolution
Withania somnifera WS-Y-08
-
the enzyme belongs to the oxidosqualene cyclase OSC superfamily of enzymes
-
malfunction
-
antisense inhibition of cycloartenol synthase results in decreased phytosterol levels and enhanced ginsenoside levels
metabolism
D6R1X1
the enzyme is involved in biosynthesis of three key withanolides namely withanolide A, withanone, and withaferin A
metabolism
Withania somnifera WS-Y-08
-
the enzyme is involved in biosynthesis of three key withanolides namely withanolide A, withanone, and withaferin A
-
physiological function
-
cycloartenol synthase is responsible for the synthesis of cycloartenol providing skeletons for phytosterols
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
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
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
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
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
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-
8-Azadecalin
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-
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
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]
SUBSTRATE
ORGANISM
UNIPROT
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]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.00019
Ochromonas malhamensis
-
-
additional information
-
-
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 7.5
-
-
6.5 - 7.5
-
-
7 - 7.3
Ochromonas malhamensis
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
Ochromonas malhamensis
-
30 min incubation
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.39
D6R1X1
sequence calculation
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
81000
-
calculated from nucleotide sequence
653100
86300
-
calculated from amino acid sequence
661372
100000
-
HPLC gel filtration
3626
110000
-
gel filtration
3630
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
D6R1X1
x * 85900, sequence calculation, x * 113000, recombinant GST-tagged enzyme, SDS-PAGE
?
Withania somnifera WS-Y-08
-
x * 85900, sequence calculation, x * 113000, recombinant GST-tagged enzyme, SDS-PAGE
-
dimer
-
2 * 55000, SDS-PAGE
dimer
-
2 * 55000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Ochromonas malhamensis
-
partial
Ochromonas malhamensis
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
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
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, cloning and expression in Escherichia coli strain D5alpha, functional expression of GST-tagged enzyme in Schizosaccharomyces pombe
D6R1X1
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the cycloartenol synthase gene in hairy root cultures elicited by 0.1 mM methyl jasmonate treatment decreases slightly
-
plant derived and microbe derived elicitors altered WsOSCs expression pattern both at mRNA and protein level which corresponded with the change in the accumulation of three key withanolides namely withanolide A, withanone, and withaferin A, overview
D6R1X1
plant derived and microbe derived elicitors altered WsOSCs expression pattern both at mRNA and protein level which corresponded with the change in the accumulation of three key withanolides namely withanolide A, withanone, and withaferin A, overview
Withania somnifera WS-Y-08
-
-
ENGINEERING
ORGANISM
UNIPROT
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