Information on EC 5.5.1.9 - Cycloeucalenol cycloisomerase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
5.5.1.9
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RECOMMENDED NAME
GeneOntology No.
Cycloeucalenol cycloisomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
Cycloeucalenol = obtusifoliol
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
elimination/addition
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intramolecular
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
7-dehydroporiferasterol biosynthesis
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Biosynthesis of secondary metabolites
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Metabolic pathways
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plant sterol biosynthesis
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Steroid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
Cycloeucalenol lyase (cyclopropane-decyclizing)
Opens the cyclopropane ring of a number of related 4alpha-methyl-9beta-19-cyclosterols, but not those with a 4beta-methyl group, with formation of an 8(9) double bond. Involved in the synthesis of plant sterols.
CAS REGISTRY NUMBER
COMMENTARY hide
60496-19-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
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Manually annotated by BRENDA team
no activity in Oryctolagus cuniculus
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
24-Methylenen pollinastanol
4-Desmethyl obtusifoliol
show the reaction diagram
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cycloeucalenol
?
show the reaction diagram
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enzyme of plant sterol metabolism
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cycloeucalenol
obtusifoliol
show the reaction diagram
additional information
?
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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
cycloeucalenol
?
show the reaction diagram
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enzyme of plant sterol metabolism
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cycloeucalenol
obtusifoliol
show the reaction diagram
Q9M643
converts pentacyclic cycloprolylsterols to conventional tetracyclic sterols
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?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,6-Dimethyl-N-tridecylmorpholine
2-Aza-2-dihydrosqualene
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25-Azacycloartenol
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3beta-Aminocycloeucalene
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0.2 mM, weak
4beta-Methylcycloeucalenol
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0.2 mM, weak
7-Keto-24,28-dihydrocycloeucalenol
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7-Oxo-24ksi(28)-dihydrocycloeucalenol
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reversible, highly specific
7alpha-Hydroxy-24,28-dihydrocycloeucalenol
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7beta-Hydroxy-24,28-dihydrocycloeucalenol
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Cycloartenol
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0.2 mM, weak
Cycloeucalenyl 3beta-methyl ether
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0.2 mM, weak
DELTA6-24,28-Dihydrocycloeucalenol
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DELTA7-24,28-Dihydrocycloeucalenol
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N-(1,5,9-Trimethyldecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol
N-Benzyl-8-aza-4alpha,10-dimethyl-trans-decal-3beta-ol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.077 - 1.53
cycloeucalenol
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as a Flag-tagged fusion protein
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expression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D260E
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 92%, wild-type: 100%. Relative activity: 135% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type. Mutant shows 6% activity with 24-methylene-24-dihydro-cycloartenol (wild-type 0%)
D260H
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 61%, wild-type: 100%. Relative activity: 5.2% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type
D260V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 0%, wild-type: 100%. Relative activity: below 1.5% (wild-type: 100%)
D260Y
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 22%, wild-type: 100%. Relative activity: 0.7% (wild-type: 100%)
E29D
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 65%, wild-type: 100%. Relative activity: 3.8% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type
E29H
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 33%, wild-type: 100%. Relative activity: 3.5% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type
E29K
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 1.7%, wild-type: 100%. Relative activity: below 0.5% (wild-type: 100%); in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 1.7% relative ergosterol synthesis (wild-type: 100%), below 0.5% in vitro microsomal CPI activity (wild-type: 100%)
E29V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 0%, wild-type: 100%. Relative activity: below 0.5% (wild-type: 100%)
E54V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 94%, wild-type: 100%
E58V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 91%, wild-type: 100%
E60V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 83%, wild-type: 100%
F111L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 88%, wild-type: 100%. Relative activity: 31% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
F116L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 37%, wild-type: 100%. Relative activity: 4.7% (wild-type: 100%)
F117L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 89%, wild-type: 100%. Relative activity: 28% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
G108A
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 92%, wild-type: 100%. Relative activity: 90% (wild-type: 100%)
G108E
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 0%, wild-type: 100%. Relative activity: below 0.5% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type; in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 0% relative ergosterol synthesis (wild-type: 100%), below 0.5% in vitro microsomal CPI activity (wild-type: 100%)
G108V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 6%, wild-type: 100%. Relative activity: 1.7% (wild-type: 100%)
G28E
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 15%, wild-type: 100%. Relative activity: 1% (wild-type: 100%); in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 15% relative ergosterol synthesis (wild-type: 100%), 1% in vitro microsomal CPI activity (wild-type: 100%)
G28V
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 46%, wild-type: 100%. Relative activity: 1.6% (wild-type: 100%)
H114L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 85%, wild-type: 100%. Relative activity: 5.2% (wild-type: 100%)
N109A
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 76%, wild-type: 100%. Relative activity: 4.6% (wild-type: 100%)
T113A
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 69%, wild-type: 100%. Relative activity: 7.2% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
T113I
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 66%, wild-type: 100%. Relative activity: 3.1% (wild-type: 100%); in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 66% relative ergosterol synthesis (wild-type: 100%), below 2.4% in vitro microsomal CPI activity (wild-type: 100%)
T113S
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 98%, wild-type: 100%. Relative activity: 73% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
W112E
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 77%, wild-type: 100%. Relative activity: 5.8% (wild-type: 100%)
W112K
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 47%, wild-type: 100%. Relative activity: 1.8% (wild-type: 100%)
W112L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 86%, wild-type: 100%. Relative activity: 49% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type. Mutant shows 69% activity with 24-methylene-24-dihydro-cycloartenol (wild-type 0%), 10% activity with cycloartenol (wild-type 0%). 32% activity with cycloartanol (wild-type 0%), 15% activity with 4beta-methyl-24-dihydro-cycloeucalenol (wild-type 0%)
Y110L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 64%, wild-type: 100%. Relative activity: 2.8% (wild-type: 100%)
Y115L
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cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 83%, wild-type: 100%. Relative activity: 4.3% (wild-type: 100%)