Information on EC 1.14.19.41 - sterol 22-desaturase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.19.41
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RECOMMENDED NAME
GeneOntology No.
sterol 22-desaturase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2 = ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + 2 H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ergosterol biosynthesis I
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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
ergosta-5,7,24(28)-trien-3beta-ol,NADPH:oxygen oxidoreductase (22,23-dehydrogenating)
A heme-thiolate protein (P450). The enzyme, found in yeast and plants, catalyses the introduction of a double bond between the C-22 and C-23 carbons of certain sterols. In yeast the enzyme acts on ergosta-5,7,24(28)-trien-3beta-ol, a step in the biosynthesis of ergosterol. The enzyme from the plant Arabidopsis thaliana acts on sitosterol and 24-epi-campesterol, producing stigmasterol and brassicasterol, respectively.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
subspecies Physcomitrella patens patens, strain Gransden Wood
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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enzyme gene erg5 deletion increases azole susceptibility but does not cause accumulation of 14alpha-methylated sterols during ketoconazole stress in Neurospora crassa
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
22-dihydrobrassicasterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
show the reaction diagram
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highest activity
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?
24-epi-campesterol + NADPH + H+ + O2
brassicasterol + crinosterol + NADP+ + H2O
show the reaction diagram
substrate for isoform CYP710A2 but not CYP710A1
brassicasterol is the major product
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?
24-epi-campesterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
show the reaction diagram
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?
24-methylcholesterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
show the reaction diagram
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?
beta-sitosterol + NADPH + H+ + O2
stigmasta-5,22-dien-3beta-ol + NADP+ + H2O
show the reaction diagram
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?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
show the reaction diagram
elionasterol + NADPH + H+ + O2
poriferasterol + NADP+ + H2O
show the reaction diagram
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?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
show the reaction diagram
ergosta-5,7-dien-3beta-ol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
show the reaction diagram
ergosta-5,7-dienol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
show the reaction diagram
sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
show the reaction diagram
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?
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
24-methylcholesterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
show the reaction diagram
Q9ZV28
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?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
show the reaction diagram
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(20S)-21-isocyano-20-methylpregn-5-en-3beta-ol
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complete inhibition at 0.15 mM
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carbon monoxide
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clotrimazole
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fluconazole
itraconazole
ketoconazole
voriconazole
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additional information
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not inhibited by desmosterol, 24-methylenecholesterol, and 24-bromocholesterol
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.0037
beta-sitosterol
0.0204
ergosta-5,7-dien-3beta-ol
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at pH 7.2 and 37°C
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0.0125
ergosta-5,7-dienol
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at pH 6.8 and 37°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.009 - 0.17
beta-sitosterol
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8.8 - 46.7
beta-sitosterol
3989
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000014
fluconazole
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at pH 7.2 and 37°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.015
(20S)-21-isocyano-20-methylpregn-5-en-3beta-ol
Saccharomyces cerevisiae
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at 27°C, pH not specified in the publication
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0.0000001 - 0.0000005
fluconazole
0.0000001
itraconazole
Candida glabrata
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calculated value, pH and temperature not specified in the publication
0.0000001 - 0.0000002
ketoconazole
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55723
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x * 55723, calculated from amino acid sequence
57028
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x * 57028, isoform CYP710A14, calculated from amino acid sequence
57410
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x * 57410, isoform CYP710A13, calculated from amino acid sequence
57511
x * 57511, calculated from amino acid sequence
58000
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x * 58000, SDS-PAGE
59000
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x * 59000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
amino-octyl Sepharose column chromatography and hydroxyapatite column chromatography
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aminooctyl-agarose column chromatography and hydroxylapatite column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in a baculovirus/Sf9 insect cell system
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme transcript increases 4fold in pericarp of ripening wild type fruit
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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mutant CA108 is an erg11 erg5 double mutant harboring a single amino acid substitution (A114S) in sterol 14DELTA-demethylase (Erg11p) and sequence repetition (10 duplicated amino acids), which nullify C22 desaturase (Erg5p) function