Information on EC 2.1.1.41 - sterol 24-C-methyltransferase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.1.1.41
-
RECOMMENDED NAME
GeneOntology No.
sterol 24-C-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + 5alpha-cholesta-8,24-dien-3beta-ol = S-adenosyl-L-homocysteine + 24-methylene-5alpha-cholest-8-en-3beta-ol
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
7-dehydroporiferasterol biosynthesis
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Biosynthesis of antibiotics
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Biosynthesis of secondary metabolites
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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
S-adenosyl-L-methionine:zymosterol 24-C-methyltransferase
Requires glutathione. Acts on a range of sterols with a 24(25)-double bond in the sidechain. While zymosterol is the preferred substrate it also acts on desmosterol, 5alpha-cholesta-7,24-dien-3beta-ol, 5alpha-cholesta-5,7,24-trien-3beta-ol, 4alpha-methylzymosterol and others. S-Adenosyl-L-methionine attacks the Si-face of the 24(25) double bond and the C-24 hydrogen is transferred to C-25 on the Re face of the double bond.
CAS REGISTRY NUMBER
COMMENTARY hide
37257-07-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
strain 76484
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Manually annotated by BRENDA team
strain 76484
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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
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Manually annotated by BRENDA team
yeast
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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
strain 427
SwissProt
Manually annotated by BRENDA team
strain 427
SwissProt
Manually annotated by BRENDA team
strain STIB900
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Manually annotated by BRENDA team
strain STIB900
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Manually annotated by BRENDA team
bean rust
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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key enzyme in the biosynthesis of ergosterol
physiological function
expression of the Pneumocystis carinii enzyme in a Saccharomyces cerevisiae erg6 knockout mutant restores its ability to produce the C28 sterol ergosterol as the major sterol, and also results in low levels of C29 sterols. In the yeast, the Pneumocystis carinii enzyme appears to be less able to add a second methyl group at the methylene function. In the transformed strain, ergosterol is the major sterol component comprising 75.2% of total sterols
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3-beta, 13alpha,17alpha)-3-fluorolanost-8,24-diene + S-adenosyl-L-methionine
(3-beta, 13alpha,17alpha)-3-fluor-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
conversion into a single 24(28)-methylene product
-
?
(3beta)-3-fluorolanost-8,24-diene + S-adenosyl-L-methionine
(3beta)-3-fluoro-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine
show the reaction diagram
-
catalytic competence: 16%
-
-
?
(3beta)-3-methoxylanosta-8,24-diene + S-adenosyl-L-methionine
(3beta)-3-methoxy-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine
show the reaction diagram
-
catalytic competence: 18%
-
-
?
(3beta)-lanosta-8,24-dien-3-amine + S-adenosyl-L-methionine
(3beta)-24-methylidenelanost-8-en-3-amine + S-adenosyl-L-homocysteine
show the reaction diagram
-
catalytic competence: 22%
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-
?
(3beta)-lanosta-8,24-dien-3-yl acetate + S-adenosyl-L-methionine
(3beta)-24-methylidenelanost-8-en-3-yl acetate + S-adenosyl-L-homocysteine
show the reaction diagram
-
catalytic competence: 29%
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-
?
14alpha-methylergosta-8,24(28)-diene + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
14alpha-methylzymosterol + S-adenosyl-L-methionine
14alpha-methyl-24-methylenezymosterol + S-adenosyl-L-homocysteine
show the reaction diagram
24(28)-methylene lophenol + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
-
?
24(28)-methylenecycloartanol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
ratio of DELTA25(27) to DELTA24(28)-product for wild-type is 100:0, 35% conversion
-
?
24(28)-methylenelophenol + S-adenosyl-L-methionine
?
show the reaction diagram
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-
-
?
24,25-dehydropollinastanol + S-adenosyl-L-methionine
?
show the reaction diagram
-
24,25-dehydropollinastanol is 14alpha-methyl-9beta,19-cyclo-5alpha-cholest-24-en-3beta-ol
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-
?
24-methylenecholesterol + S-adenosyl-L-methionine
24-ethylidenecholesterol + S-adenosyl-L-homocysteine
show the reaction diagram
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5% the reaction rate of zymosterol
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?
24-methylenelanosterol + S-adenosyl-L-methionine
pneumocysterol + S-adenosyl-L-homocysteine
show the reaction diagram
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preferred substrate
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?
26,27-dehydrozymosterol + S-adenosyl-L-methionine
26-homo-cholesta-8(9),23(24)E,26(26')-trienol + 26-homo-cholesta-8(9),26(26')-3beta,24beta-dienol + S-adenosyl-L-homocysteine
show the reaction diagram
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mutants
-
?
26,27-dehydrozymosterol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
in contrast to the results with zymosterol, product analysis of the 26,27-dehydrozymosterol assays shows that multiple products are produced that occurred in different ratios determined by HPLC-radiocounting of the non-saponifiable lipid fractions. In these analyses two major product classes are identified, a neutral C26 sterol monol and a pair of C26-oxygenated diols
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?
26-difluorocycloartenol + S-adenosyl-L-methionine
26-difluoro-25-hydroxy-24-methylcycloartanol + S-adenosyl-L-homocysteine
show the reaction diagram
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products are 26-difluorocyclolaudenol (monol), 26-difluoro-24(28)-methylenecycloartanol (monol) and 26-difluoro-25-hydroxy-24-methylcycloartanol (diol) distributed in a ratio of 6:4:90 at approximately 1% yield
-
?
26-fluorocycloartenol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
reaction affords a bound intermediate that converts in favour of the DELTA25(27)-olefin product via the cyclolaudenol cation formed initially during the C-24-methylation reaction
hydrolysis of the product gives 26-fluoro-25-hydroxy-24-methylcycloartanol
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?
26-homocycloartenol + S-adenosyl-L-methionine
24-methylene-26-homocycloartenol + S-adenosyl-L-homocysteine
show the reaction diagram
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single product
-
?
31-norcycloartenol + S-adenosyl-L-methionine
24-methylene-31-norcycloartenol + S-adenosyl-L-homocysteine
show the reaction diagram
-
31-norcycloartenol is 4,14alpha-dimethyl-9beta,19-cyclo-5alpha-cholest-24-en-3beta-ol
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-
?
31-norlanosterol + S-adenosyl-L-methionine
?
show the reaction diagram
4alpha-methylzymosterol + S-adenosyl-L-methionine
?
show the reaction diagram
5-dehydroepisterol + S-adenosyl-L-methionine
?
show the reaction diagram
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-
-
-
?
agnosterol + S-adenosyl-L-methionine
24-methyleneagnosterol + S-adenosyl-L-homocysteine
show the reaction diagram
-
agnosterol is 4,4,14alpha-trimethyl-5alpha-cholesta-7(8),9(11),24-trien-3beta-ol
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-
?
cholesta-5,7,24-triene + S-adenosyl-L-methionine
?
show the reaction diagram
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?
cholesta-5,7,24-trienol + S-adenosyl-L-methionine
?
show the reaction diagram
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?
cholesta-7,24-diene + S-adenosyl-L-methionine
?
show the reaction diagram
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-
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?
cholesterol + S-adenosyl-L-methionine
?
show the reaction diagram
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?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylene cycloartanol + S-adenosyl-L-homocysteine
show the reaction diagram
-
optimal substrate for SMT1
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-
?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylenecycloartanol + S-adenosyl-L-homocysteine
show the reaction diagram
-
ratio of DELTA25(27) to DELTA24(28)-product for wild-type is 57:43, 70% conversion
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
show the reaction diagram
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-
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-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartenol + S-adenosyl-L-homocysteine
show the reaction diagram
cycloartenol 3-ketone + S-adenosyl-L-methionine
?
show the reaction diagram
-
cycloartenol 3-ketone is 4,4,14alpha-trimethyl-9beta,19-cyclo-5alpha-cholest-24-en-3-one
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?
dehydroergosterol + S-adenosyl-L-methionine
?
show the reaction diagram
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-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
show the reaction diagram
ergosta-5,8,22,24(28)-tetraene + S-adenosyl-L-methionine
?
show the reaction diagram
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-
-
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?
ergosterol + S-adenosyl-L-methionine
?
show the reaction diagram
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?
lanost-24-enol + S-adenosyl-L-methionine
24-methylene-lanost-24-erol + S-adenosyl-L-homocysteine
show the reaction diagram
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lanost-24-enol is 4,4,14alpha-trimethyl-5alpha-cholesta-9(11),24-dien-3beta-ol
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?
lanosta-7,24-dienol + S-adenosyl-L-methionine
24-methylene-lanost-7,24-dienol + S-adenosyl-L-homocysteine
show the reaction diagram
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lanosta-7,24-dienol is 4,4,14alpha-trimethyl-5alpha-cholesta-7(8),24-dien-3beta-ol
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?
lanosta-8,24-dien-3-one + S-adenosyl-L-methionine
24-methylidenelanost-8-en-3-one + S-adenosyl-L-homocysteine
show the reaction diagram
-
catalytic competence: 48%
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-
?
lanosterol + + S-adenosyl-L-methionine
24beta-methyllanosta-8,25(27)-enol + 38% 24(28)-methylenelanosterol + S-adenosyl-L-homocysteine
show the reaction diagram
-
products are 55% 24beta-methyllanosta-8,25(27)-enol, 38% 24(28)-methylenelanosterol (eburicol), and 7% 24beta-ethyllanosta-8,25(27)-enol
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
show the reaction diagram
lanosterol-3beta-OH + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
show the reaction diagram
-
catalytic competence: 100%
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?
obtusifoliol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + 26,27-dehydrolanosterol
?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 31-norlanosterol
?
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + 5alpha-cholesta-8,24-dien-3beta-ol
S-adenosyl-L-homocysteine + 24-methylene-5alpha-cholest-8-en-3beta-ol
show the reaction diagram
-
3-hydroxy-3-methylglutaryl CoA reductase and C24-sterol methyltransferase type 1 work in concert to control carbon flux into end-product sterols. Sterol composition can be controlled by the temporal activity of the promoters driving transgene expression
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-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartenol
show the reaction diagram
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?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24-methylene-24,25-dihydrolanosterol
show the reaction diagram
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-
-
-
?
S-adenosyl-L-methionine + zymosterol
?
show the reaction diagram
-
GC-MS analysis of the enzyme-generated products from a soluble TbSMT shows the presence of four biomethylated sterols identified as ergosta-8,25(27)-dienol, ergosta-8,24(28)-dienol, ergosta-8,24(25)-dienol and 24-dimethyl ergosta-8,25(27)-dienol in a ratio of substrate/product of 7:3. The products distributed in a ratio of approximately 5:1:2:2 respectively
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?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
show the reaction diagram
zymosterol + S-adenosyl-L-methionine
24-methylzymosta-8,25(27)-dienol + S-adenosyl-L-homocysteine
show the reaction diagram
-
mutants D79L and E82L
-
?
zymosterol + S-adenosyl-L-methionine
?
show the reaction diagram
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
show the reaction diagram
additional information
?
-
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
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartenol + S-adenosyl-L-homocysteine
show the reaction diagram
S-adenosyl-L-methionine + 5alpha-cholesta-8,24-dien-3beta-ol
S-adenosyl-L-homocysteine + 24-methylene-5alpha-cholest-8-en-3beta-ol
show the reaction diagram
-
3-hydroxy-3-methylglutaryl CoA reductase and C24-sterol methyltransferase type 1 work in concert to control carbon flux into end-product sterols. Sterol composition can be controlled by the temporal activity of the promoters driving transgene expression
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no metal ion required
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(24,S),25-epiminozymosterol
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(24R)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
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(24R)-24-methyl-25-azacycloartenol
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(24R)-methyl-25-thiacholesteryl iodide
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(24R,S),25-epiminolanosterol
(24R,S),25-epiminozymosterol
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(24R,S)-24-Ethyl-25-azacycloartenol
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(24R,S)-24-Methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
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(24R,S)-24-Methyl-25,26,27-trisnor-24-dimethylsulfonium cycloartenol iodide
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-
(24R,S)-24-Methyl-25,26,27-trisnor-24-trimethylarsonium cycloartenol iodide
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(24R,S)-24-Methyl-25-azacycloartenol
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(24S)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
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-
(24S)-24-methyl-25-azacycloartenol
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(24S)-methyl-25-thiacholesteryl iodide
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(3beta,24,R,S)-24-methyl-24-thioniacholest-5-enol
-
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(3S,20R)-20-(propylamino-ethyl)-pregn-7-en-3-ol
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(3S,20S)-20-(butylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(ethylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(methylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(pentylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-(propylamino-methyl)-pregn-7-en-3-ol
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(3S,20S)-20-[(1R,S)-(1,2-dimethyl-propylamino)-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(2-dimethylamino-ethylamino)-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(2-methylpropyl)amino-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(2-pyrrolidin-1-yl-ethylamino)-methyl]-pregn-7-en-3-ol
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(3S,20S)-20-[(3-dimethylamino-propylamino)-methyl]-pregn-7-en-3-ol
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(R,S)-24,25-epiminolanosterol
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(R,S)-S-butyl-S-[(3S,20S)-(3-hydroxypregn-7-en-20-yl)-methyl]-S-methyl-sulfonium iodide
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2-(3S,20R)-[(E)-2-(3-hydroxypregn-7-en-20-yl)-ethenyl]-1-methylpyridinium iodide
-
-
22,25-Diazacholesterol
-
20R and 20S isomer
22,26-azasterol
22-piperidin-3-yl-pregnan-22(S),3beta-diol
-
-
23-Azacholesterol
24(28)-methylene cycloartanol
-
-
24(28)-methylenecycloartanol
-
noncompetitive with respect to S-adenosyl-L-methionine
24(28)-methylenecycloartenol
-
-
24(R,S),25-epiminolanosterol
24(R,S),25-epiminozymosterol
-
reversible inhibitor, disrupts ergosterol homoeostasis by interrupting methyl addition to C-24 thereby impairing growth
24(R,S)-25-epiminolanosterol
-
-
24(S)-24-methyl-25-thiacholest-5-enol iodide
-
-
24-Azacholesterol
24-Azacycloartanyl acetate
-
-
24-Methyl-25,26,27-trisnor-24-trimethylammonium cycloartenol iodide
-
24R and 24S isomer
24-Methyl-25-azacycloartenol
-
24R and 24S isomer
24-Oxo-25-azacycloartenol
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24-thialanosterol
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24beta-aminolanosterol
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25,26,27-Trisnor-24-trimethylammonium cycloartenol iodide
-
-
25-aminolanosterol
-
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25-aza-24,25-dihydrolanosterol
-
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25-Aza-24,25-dihydrozymosterol
-
-
25-azacholestane
-
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25-Azacholestanol
-
-
25-Azacholesterol
25-Azacholesterol hydrochloride
-
-
25-Azacycloartenol
25-azacyloartenol
-
-
25-azalanosterol
25-thiacholesterol iodide
-
-
25-thialanosterol iodide
-
-
26,27-dehydrolanosterol
-
-
26,27-dehydrozymosterol
26-difluorocycloartenol
-
competitive inhibitor
-
26-fluorocycloartenol
-
competitive inhibitor
-
26-nor-25-thialanosterol
-
-
3-aminolanosterol
-
-
30-amino-24,25-dihydrolanosterol
-
-
4-(3S,20R)-[(E)-2-(3-hydroxypregn-7-en-20-yl)-ethenyl]-1-methylpyridinium iodide
-
-
5'-deoxy-5'-(methylthio)adenosine
-
AdoMet analog, competitive inhibitor
7-amino-24,25-dihydrolanosterol
-
-
Amphotericin B
-
-
amphotericine B
-
inhibits the wild-type at concentrations above 60 nM, inhibition can be hindered by zymosterol
cholesta-8,24(28)-dienol
-
-
cyclolaudanol
-
-
cyclolaudenol
-
dead-end inhibitor, competitive versus cycloartenol and uncompetitive versus S-adenosyl-L-methionine
desmosterol
ergosta-5,7,22-trienol
-
-
ergosterol
Filipin
-
slightly inhibiting at low concentration
itraconazole
-
-
ketoconazole
methyl ([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)acetate
-
-
methyl 3-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)propanoate
-
-
methyl 4-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)butanoate
-
-
methyl 5-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)pentanoate
-
-
methyl 6-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)hexanoate
-
-
methyl 7-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)heptanoate
-
-
methyl 8-([2-[(3S,8S,9S,10R,13S,14S,17R)-3-(acetyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]amino)octanoate
-
-
Nystatin
-
slightly inhibiting at low concentration
S-adenosyl-L-homocysteine
S-isobutyladenosine
-
AdoMet analog, competitive inhibitor
sinefungin
-
AdoMet analog, competitive inhibitor
sitosterol
-
-
Substrate analogues
-
dead-end inhibitors
-
Triparanol
-
-
Zymosterol
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
amphotericine B
-
activates at concentrations below 5.4 nM, optimal at 2.1 nM, wild-type and mutant
candicidin
-
stimulates, best at low concentration
Filipin
-
slightly activating at high concentration
glutathione
-
required
Nystatin
-
slightly activating at high concentration
pimaricin
-
strong activation, activation level decreases with increasing concentration of pimaricin
additional information
-
no cofactor requirement
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.033
14alpha-Methylzymosterol
-
-
0.03 - 0.05
24(28)-methylene lophenol
0.043
24,25-Dehydropollinastanol
-
-
0.019
24-methylenelanosterol
0.013 - 0.074
26,27-dehydrozymosterol
0.044
26-difluorocycloartenol
-
pH 7.5, 35C
-
0.036
26-fluorocycloartenol
0.035
31-norlanosterol
-
pH 7.5, 37C, Vmax 45 pmol/min
0.016 - 0.03
AdoMet
0.13
Agnosterol
-
-
0.125
Cholesta-5,7,24-trienol
-
-
0.028 - 0.045
Cycloartenol
0.067 - 0.281
desmosterol
0.0106 - 0.038
lanosterol
0.0334
S-adenosyl-L-methionine
-
-
0.006 - 0.075
Zymosterol
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.005
24(28)-methylene lophenol
0.0001167 - 0.003333
26,27-dehydrozymosterol
0.003 - 0.01
AdoMet
0.01
Cycloartenol
0.0023
lanosterol
Paracoccidioides brasiliensis
-
pH 7.5, 37C
0.0001 - 0.01333
Zymosterol
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.018
24(28)-methylenecycloartanol
Chlamydomonas reinhardtii
A8IJ34
pH not specified in the publication, temperature not specified in the publication
11564
0.02
24(28)-methylenelophenol
Chlamydomonas reinhardtii
A8IJ34
pH not specified in the publication, temperature not specified in the publication
13763
0.025
Cycloartenol
Chlamydomonas reinhardtii
A8IJ34
pH not specified in the publication, temperature not specified in the publication
1530
0.024
lanosterol
Chlamydomonas reinhardtii
A8IJ34
pH not specified in the publication, temperature not specified in the publication
1188
0.019
obtusifoliol
Chlamydomonas reinhardtii
A8IJ34
pH not specified in the publication, temperature not specified in the publication
5588
0.022
Zymosterol
Chlamydomonas reinhardtii
A8IJ34
pH not specified in the publication, temperature not specified in the publication
1067
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00001
(24,S),25-epiminozymosterol
-
-
0.000015
(24R)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
-
-
0.00002
(24R)-24-methyl-25-azacycloartenol
-
-
0.0000017 - 0.000003
(24R)-methyl-25-thiacholesteryl iodide
0.00001
(24R,S),25-epiminolanosterol
-
-
0.000085
(24R,S)-24-Ethyl-25-azacycloartenol
-
-
0.00005
(24R,S)-24-Methyl-25,26,27-trisnor-24-dimethylsulfonium cycloartenol iodide
-
-
0.000025
(24R,S)-24-Methyl-25,26,27-trisnor-24-trimethylarsonium cycloartenol iodide
-
-
0.00002
(24R,S)-24-Methyl-25-azacycloartenol
-
-
0.000045
(24S)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
-
-
0.00003
(24S)-24-methyl-25-azacycloartenol
-
-
0.0000023 - 0.0000046
(24S)-methyl-25-thiacholesteryl iodide
0.000016
(3beta,24,R,S)-24-methyl-24-thioniacholest-5-enol
-
-
0.00009
23-Azacholesterol
0.085
24(28)-methylenecycloartenol
-
-
0.000003 - 0.000049
24(R,S),25-epiminolanosterol
0.000025 - 0.00036
24(R,S)-25-epiminolanosterol
0.00018
24-Azacholesterol
-
-
0.00003
24-Azacycloartanyl acetate
-
-
0.000035
24-Methyl-25,26,27-trisnor-24-trimethylammonium cycloartenol iodide
-
-
0.00017
24-Oxo-25-azacycloartenol
-
-
0.000035
25,26,27-Trisnor-24-trimethylammonium cycloartenol iodide
-
-
0.00000125 - 0.000003
25-Aza-24,25-dihydrozymosterol
0.000048
25-azacholestane
-
-
0.000045
25-Azacholesterol
-
-
0.000015
25-Azacholesterol hydrochloride
-
-
0.000002 - 0.000045
25-Azacycloartenol
0.00004
25-azacyloartenol
-
-
0.000014 - 0.00039
25-azalanosterol
0.0000011 - 0.0000024
25-thiacholesterol iodide
0.000054
26,27-dehydrolanosterol
-
pH 7.5, 37C
0.000009 - 0.029
26,27-dehydrozymosterol
0.093
26-difluorocycloartenol
-
pH 7.5, 35C
-
0.071
26-fluorocycloartenol
-
pH 7.5, 35C
-
0.022
5'-deoxy-5'-(methylthio)adenosine
-
-
0.072
cholesta-8,24(28)-dienol
-
pH 7.5, 30C
0.023
cyclolaudanol
-
-
0.009 - 0.489
desmosterol
0.02
ergosta-5,7,22-trienol
-
pH 7.5, 30C
0.00071 - 0.08
ergosterol
0.058
S-isobutyladenosine
-
-
0.013
sinefungin
-
-
0.0001
sitosterol
-
-
0.00000000075
solasodine
-
-
0.0045 - 0.022
Zymosterol
additional information
additional information
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0035
22,26-azasterol
Leishmania major
-
-
0.005
24(R,S),25-epiminolanosterol
Candida albicans
-
pH 7.5, 30C
0.02
24-thialanosterol
Candida albicans
-
pH 7.5, 30C
0.000014 - 0.003
25-azalanosterol
0.00176 - 0.00243
azasterol
0.00383
ketoconazole
Leishmania major
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000082
bloodstream forms
0.00000217
procyclic forms
0.0008
-
purified enzyme
0.00124
-
purified enzyme
0.53
-
purified enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 7.7
7.5 - 8
-
assay at
7.6
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10
-
slightly active at pH 5.5, no activity at pH 10
5.5 - 9
-
recombinant enzyme
5.5 - 8.5
-
-
6.5
-
half maximum velocities at 6.5 and 9.0
6.8 - 7.7
-
less than half-maximal activity above and below
6.8 - 7.5
-
-
7.5 - 8
-
optimum pH
9
-
half maximum velocities at 6.5 and 9.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
-
assay at
37
-
recombinant enzyme
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
15 - 30
-
less than half-maximal activity above and below
22 - 45
-
recombinant enzyme
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
weak expression, determined by RT-PCR
Manually annotated by BRENDA team
-
highest expression, determined by RT-PCR
Manually annotated by BRENDA team
-
etiolated
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
by immunofluorescence and electron microscopy studies it is shown that sterol methenyltransferase is primarily associated to the endoplasmic reticulum. In addition to this localisation, the protein is incorporated into translucent vesicles presumably of the endocytic pathway
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39800
predicted from sequence, SDS-PAGE
40000
-
predicted from cDNA
42500
-
calculated from cDNA
43000
-
SDS-PAGE
150000
-
gel filtration
160000
172000
-
gel filtration
178000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetramer
additional information
-
cooperativity among the subunits
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
no stabilization by MgCl2, CaCl2, DTT, reduced glutathione, phosphatidylcholine
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, 1 month, less than 10% loss of activity
-
4C, 0.1 M Tris-HCl buffer, 1 mM Mg2+, 90% loss of activity overnight
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
isoform SMT2-2 is purified to homogeneity by column chromatography, gel filtration
-
partial
partial, recombinant from E. coli
recombinant mutant from E. coli; recombinant wild-type from E. coli
-
recombinant protein, SDS-PAGE; using Ni-NTA-chromatography
recombinant wild-type from E. coli
-
recombinant wild-type SMT is expressed and partially purified by anionic-exchange chromatography to generate ca. 85% pure Erg6p as determined by SDS-PAGE quantification of the target protein
-
to homogeneity
-
using anion exchange chromatography, gel filtration and fast performance liquid chromatography using a Mono Q column
-
using Ni-NTA chromatography
-
wild-type and mutant enzymes
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
coexpression of the catalytic domain of Hevea brasiliensis 3-hydroxy-3-methylglutaryl CoA reductase and Nicotiana tabacum C24-sterol methyltransferase type 1 in tobacco, under control of both constitutive and seed-specific promoters, resulting in increased accumulation of total sterol in seed tissue by 2.5fold and 2.1fold, respectively
-
expressed as a His-tagged fusion protein in Escherichia coli; pET-28a vector, expressed in Escherichia coli Rosetta, recombinant protein
expressed as a recombinant fusion protein in Escherichia coli BL21
-
expressed in Escherichia coli
-
expressed in Escherichia coli; expressed in Escherichia coli, recombinant protein, site-directed mutagenesis
expression as FLAG-fusion protein in Escherichia coli, amino acid sequence analysis
-
expression in Escherichia coli
expression in Escherichia coli, His-tagged protein
-
expression in Escherichia coli, wild-type and mutant enzymes
-
expression in Saccharomyces cerevisiae mutant line erg6, which is deleted in the C-24-sterol methyltransferase, via Escherichia coli, complementation of the yeast, amino acid sequence comparison
-
expression in Saccharomyces cerevisiae mutant line erg6, which is deleted in the SMT1 gene, complementation of the yeast
expression of exchange mutants in Escherichia coli; overexpression in Escherichia coli
-
into pET28a(+) and expressed with a His tag at the amino terminus in Escherichia coli BL21(DE3)
overexpressed in Escherichia coli HMS-174 cells
-
overexpression in Escherichia coli
-
overexpression of the pET vector in Escherichia coli BL21(DE3)
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcriptional regulation of soybean SMT2 genes is influenced by environmental conditions to some extent: analysis of transcript abundance by qRT-PCR reveals that both the genes SMT2-1 and SMT2-2 are down-regulated after dehydration and markedly induced under cold conditions. ABA treatment elicits an increase in transcript levels for both the genes. A reduction in expression is associated with the salinity treatment for both the genes
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Y110F
no significant change in products
Y110L
remodeling the active site to alter the electronics results in delayed timing of the hydride migration from methyl attack of the DELTA24-bond, that thereby produces metabolic switching of product ratios in favor of DELTA25(27)-olefins or impairs the second C1-transfer activity
F82I
-
continues to catalyze strongly both the first and second C1-transfer activities and generates product sets similar to the control
F82L
-
first C1-transfer activity is relatively unaffected, loss of the second C1-transfer activity
F85L
-
first C1-transfer activity is relatively unaffected, loss of the second C1-transfer activity
F91L
-
first C1-transfer activity reduced from the control activity, loss of the second C1-transfer activity
F93L
-
first C1-transfer activity reduced from the control activity, loss of the second C1-transfer activity
W87L
-
first and second C1-transfer activities are greatly reduced from the control activities
Y83F
-
first C1-transfer activity is relatively unaffected whereas the second C1-transfer activity generates different amounts of product compared to the control
Y83L
-
first C1-transfer activity greatly reduced from the control activity, loss of the second C1-transfer activity
A193L
no activity; no enzyme activity
A193S
95% relative enzyme activity; relative activity: 95%
A196L
73% relative enzyme activity; relative activity: 73%
A200L
4% relative enzyme activity; relative activity: 4%
A221L
25% relative enzyme activity; relative activity: 25%
A350L
100% relative enzyme activity; relative activity: 100%
C128S
-
Km (mM) (substrate: AdoMet): 30, kcat (1/sec) (substrate: AdoMet): 0.005, Kd (mM) (zymosterol): 0.005, Kd (mM) (AdoMet): 0.008
C198L
95% relative enzyme activity; relative activity: 95%
C198V
16% relative enzyme activity; relative activity: 16%
D229L
relative activity: 100%
E224L
relative activity: 74%
E82D
55% relative enzyme activity; relative activity: 55%
E82Q
90% relative enzyme activity; relative activity: 90%
F178L
34% relative enzyme activity; relative activity: 34%
F183L
100% relative enzyme activity
F188L
2% relative enzyme activity; relative activity: 2%
F220L
29% relative enzyme activity; relative activity: 29%
F269L
no activity; no enzyme activity
F357L
100% relative enzyme activity; relative activity: 100%
F89L
100% relative enzyme activity; relative activity: 100%
F91L
15% relative enzyme activity; relative activity: 15%
G127L
1% relative enzyme activity; relative activity: 1%
G129L
no activity; no enzyme activity
G131L
5% relative enzyme activity; relative activity: 5%
G132L
50% relative enzyme activity; relative activity: 50%
G217L
100% relative enzyme activity, mutant can perform C2-transfer activity to give 24-ethyl(idene)-sterols; relative activity: 100%
G218L
100% relative enzyme activity, mutant can perform C2-transfer activity to give 24-ethyl(idene)-sterols; relative activity: 100%
G347L
5% relative enzyme activity; relative activity: 5%
G351L
90% relative enzyme activity; relative activity: 90%
G352L
3% relative enzyme activity; relative activity: 3%
G84L
14% relative enzyme activity; relative activity: 14%
G86L
16% relative enzyme activity; relative activity: 16%
H199Q
45% relative enzyme activity; relative activity: 45%
H199R
20% relative enzyme activity; relative activity: 20%
H224L
-
the ratio of turnover-number to KM-value for zymosterol is 1.4fold lower than the wild-type ratio
H90Q
no activity; no enzyme activity
H90R
no activity; no enzyme activity
I194L
67% relative enzyme activity; relative activity: 67%
K215L
100% relative enzyme activity; relative activity: 100%
K353L
56% relative enzyme activity
P201L
58% relative enzyme activity; relative activity: 58%
P216L
65% relative enzyme activity; relative activity: 65%
S354L
100% relative enzyme activity; relative activity: 100%
S87E
100% relative enzyme activity
S87L
100% relative enzyme activity; relative activity: 100%
S87Q
100% relative enzyme activity
S88L
61% relative enzyme activity; relative activity: 61%
S88N
17% relative enzyme activity; relative activity: 17%
S97E
relative activity: 100%
S97Q
relative activity: 100%
T197L
93% relative enzyme activity; relative activity: 93%
T219L
32% relative enzyme activity, mutant can perform C2-transfer activity to give 24-ethyl(idene)-sterols
V126L
1% relative enzyme activity; relative activity: 1%
V130L
100% relative enzyme activity; relative activity: 100%
V222L
27% relative enzyme activity
V349L
47% relative enzyme activity; relative activity: 47%
W225F
100% relative enzyme activity; relative activity: 60%
W225L
100% relative enzyme activity; relative activity: 100%
W286F
100% relative enzyme activity; relative activity: 51%
W286L
2% relative enzyme activity; relative activity: 2%
W85F
100% relative enzyme activity; relative activity: 55%
W85L
40% relative enzyme activity; relative activity: 40%
Y192F
100% relative enzyme activity, mutant can perform C2-transfer activity to give 24-ethyl(idene)-sterols
Y192L
95% relative enzyme activity
Y207F
100% relative enzyme activity; relative activity: 100%
Y207L
3% relative enzyme activity; relative activity: 3%
Y223F
100% relative enzyme activity, mutant can perform C2-transfer activity to give 24-ethyl(idene)-sterols; relative activity: 100%
Y223L
100% relative enzyme activity; relative activity: 100%
Y287L
20% relative enzyme activity; relative activity: 20%
Y74F
100% relative enzyme activity; relative activity: 100%
Y74L
100% relative enzyme activity; relative activity: 100%
Y81A
-
Km (mM): 0.018 (zymosterol), 0.023 (26,27-dehydrozymosterol), kcat (1/sec): 0.00083 (zymosterol), 0.000116 (26,27-dehydrozymosterol), Ki (mM): 0.011 (26,27-dehydrozymosterol), 0.00019 (25-azalanosterol), 0.00013 (24(R,S),25-epiminolanosterol), 0.071 (ergosterol)
Y81I
-
Km (mM): 0.021 (zymosterol), 0.027 (26,27-dehydrozymosterol), kcat (1/sec): 0.00433 (zymosterol), 0.00025 (26,27-dehydrozymosterol), Ki (mM): 0.009 (26,27-dehydrozymosterol), 0.00020 (25-azalanosterol), 0.00016 (24(R,S),25-epiminolanosterol), 0.077 (ergosterol)
Y81V
-
Km (mM): 0.026 (zymosterol), 0.024 (26,27-dehydrozymosterol), kcat (1/sec): 0.00116 (zymosterol), 0.00011 (26,27-dehydrozymosterol), Ki (mM): 0.007 (26,27-dehydrozymosterol), 0.000195 (25-azalanosterol), 0.000145 (24(R,S),25-epiminolanosterol), 0.074 (ergosterol)
Y81W
-
Km (mM): 0.017 (zymosterol), 0.023 (26,27-dehydrozymosterol), kcat (1/sec): 0.0133 (zymosterol), 0.0033 (26,27-dehydrozymosterol), Ki (mM): 0.010 (26,27-dehydrozymosterol), 0.00039 (25-azalanosterol), 0.00036 (24(R,S),25-epiminolanosterol), 0.088 (ergosterol)
Y83F
95% relative enzyme activity; relative activity: 95%
Y83L
90% relative enzyme activity; relative activity: 90%
Y83W
100% relative enzyme activity; relative activity: 100%
Y177F
-
mutant proteins catalyses zymosterol much less efficiently than the wild-type enzyme, with a Vmax/Km ratio 23-40% that of wild-type
Y208F
-
mutant proteins catalyses zymosterol much less efficiently than the wild-type enzyme, with a Vmax/Km ratio 23-40% that of wild-type
Y66F
-
mutant proteins catalyses zymosterol much less efficiently than the wild-type enzyme, with a Vmax/Km ratio 23-40% that of wild-type. Sterol composition of the Y66F catalysis is different. The sterol mixture possesses a significant decrease in ergosta-8,24(25)-dienol compensated by an increase in ergosta-8,25(27)-dienol and ergosta-8,24(28)-dienol
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
degradation
drug development
medicine
synthesis
-
rational drug target design based on structure-function-relation
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