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(3beta)-3-fluorolanost-8,24-diene + S-adenosyl-L-methionine
(3beta)-3-fluoro-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine
-
catalytic competence: 16%
-
-
?
(3beta)-3-methoxylanosta-8,24-diene + S-adenosyl-L-methionine
(3beta)-3-methoxy-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine
-
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
-
catalytic competence: 22%
-
-
?
(3beta)-lanosta-8,24-dien-3-yl acetate + S-adenosyl-L-methionine
(3beta)-24-methylidenelanost-8-en-3-yl acetate + S-adenosyl-L-homocysteine
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catalytic competence: 29%
-
-
?
14alpha-methylergosta-8,24(28)-diene + S-adenosyl-L-methionine
?
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-
-
-
?
14alpha-methylzymosterol + S-adenosyl-L-methionine
14alpha-methyl-24-methylenezymosterol + S-adenosyl-L-homocysteine
24(28)-methylenecycloartanol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
-
ratio of DELTA25(27) to DELTA24(28)-product for wild-type is 100:0, 35% conversion
-
?
24(28)-methylenelophenol + S-adenosyl-L-methionine
?
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-
-
?
24-methylenecholesterol + S-adenosyl-L-methionine
24-ethylidenecholesterol + S-adenosyl-L-homocysteine
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5% the reaction rate of zymosterol
-
?
24-methylenelanosterol + S-adenosyl-L-methionine
pneumocysterol + S-adenosyl-L-homocysteine
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preferred substrate
-
?
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
-
mutants
-
?
26,27-dehydrozymosterol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
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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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-
?
31-norlanosterol + S-adenosyl-L-methionine
?
4alpha-methylzymosterol + S-adenosyl-L-methionine
?
5-dehydroepisterol + S-adenosyl-L-methionine
?
-
-
-
-
?
cholesta-5,7,24-triene + S-adenosyl-L-methionine
?
-
-
-
-
?
cholesta-7,24-diene + S-adenosyl-L-methionine
?
-
-
-
-
?
cholesterol + S-adenosyl-L-methionine
?
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylenecycloartanol + S-adenosyl-L-homocysteine
-
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
dehydroergosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
ergosta-5,8,22,24(28)-tetraene + S-adenosyl-L-methionine
?
-
-
-
-
?
ergosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
lanosta-8,24-dien-3-one + S-adenosyl-L-methionine
24-methylidenelanost-8-en-3-one + S-adenosyl-L-homocysteine
-
catalytic competence: 48%
-
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
lanosterol + S-adenosyl-L-methionine
24beta-methyllanosta-8,25(27)-enol + 24(28)-methylenelanosterol + S-adenosyl-L-homocysteine
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products are 55% 24beta-methyllanosta-8,25(27)-enol, 38% 24(28)-methylenelanosterol (eburicol), and 7% 24beta-ethyllanosta-8,25(27)-enol
-
?
lanosterol-3beta-OH + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
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catalytic competence: 100%
-
-
?
obtusifoliol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
-
-
-
?
S-adenosyl-L-methionine + 24(28)-methylene cycloartenol
S-adenosyl-L-homocysteine + 24(28)-ethylidene cycloartenol
-
-
-
?
S-adenosyl-L-methionine + 24(28)-methylene lophenol
S-adenosyl-L-homocysteine + 24(28)-ethylidene lophenol
-
-
-
?
S-adenosyl-L-methionine + 26,27-dehydrolanosterol
?
-
-
-
-
?
S-adenosyl-L-methionine + 31-norlanosterol
?
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartanol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol + 24(28)-methylene cycloartanol
reaction of EC 2.1.1.142
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-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24-methylene-24,25-dihydrolanosterol
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-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24beta-methyl lanosta-8,25(27)-enol + 24(28)-methylene lanosterol
reaction of EC 2.1.1.142
-
-
?
S-adenosyl-L-methionine + obtusifoliol
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + zymosterol
?
-
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
zymosterol + S-adenosyl-L-methionine
24-methylzymosta-8,25(27)-dienol + S-adenosyl-L-homocysteine
-
mutants D79L and E82L
-
?
zymosterol + S-adenosyl-L-methionine
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
additional information
?
-
14alpha-methylzymosterol + S-adenosyl-L-methionine
14alpha-methyl-24-methylenezymosterol + S-adenosyl-L-homocysteine
-
37% activity compared to lanosterol
-
-
?
14alpha-methylzymosterol + S-adenosyl-L-methionine
14alpha-methyl-24-methylenezymosterol + S-adenosyl-L-homocysteine
-
37% activity compared to lanosterol
-
-
?
31-norlanosterol + S-adenosyl-L-methionine
?
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78% activity compared to lanosterol
-
-
?
31-norlanosterol + S-adenosyl-L-methionine
?
-
78% activity compared to lanosterol
-
-
?
4alpha-methylzymosterol + S-adenosyl-L-methionine
?
-
43% activity compared to lanosterol
-
-
?
4alpha-methylzymosterol + S-adenosyl-L-methionine
?
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43% activity compared to lanosterol
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
desmosterol is 5alpha-cholesta-5,24-dien-3beta-ol
-
-
?
desmosterol + S-adenosyl-L-methionine
24-methylenedesmosterol + S-adenosyl-L-homocysteine
-
desmosterol is 5alpha-cholesta-5,24-dien-3beta-ol
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
-
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
no reaction with
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-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
100% activity, lanosterol is the optimal acceptor molecule
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-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
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100% activity, lanosterol is the optimal acceptor molecule
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-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
preferred substrate
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
-
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
lanosterol is 4,4,14alpha-trimethyl-5alpha-cholesta-8,24-dien-3-ol
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-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
-
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
-
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
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-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
-
-
-
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?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
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the active center is composed of a set of acidic amino acids, Asp125, Asp152, Glu195 and Asp276, which contribute to initial binding of sterol and S-adenosyl-L-methionine. His90 functions subsequently in the reaction process to promote product formation
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-
?
zymosterol + S-adenosyl-L-methionine
?
-
61% activity compared to lanosterol
-
-
?
zymosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
zymosterol is 5alpha-cholesta-8,24-dien-3beta-ol
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
role in biosynthesis of plant and fungi sterols
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-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
ratio of DELTA25(27) to DELTA24(28)-product for wild-type is 28:72, 70% conversion
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
fecosterol is 24-exomethylene-5alpha-cholesta-8,24-dien-3beta-ol
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
wild-type and mutants
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
regio- and stereospecific for substrates
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
regio- and stereospecific for substrates
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
zymosterol is 5alpha-cholesta-8,24-dien-3beta-ol
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
zymosterol is 5alpha-cholesta-8,24-dien-3beta-ol
fecosterol is 24-exomethylene-5alpha-cholesta-8,24-dien-3beta-ol
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
role in biosynthesis of plant and fungi sterols
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
the enzyme catalyzes an enzymatic step following C-4 demethylation of 4,4-dimethylzymosterol. Erg28p anchors the C-4 demethylation enzyme complex to the endoplasmic reticulum and acts as a protein bridge to the Erg6p enzyme required for the next ergisterol biosynthetic step
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
a bisubstrate reaction that proceeds by a sequential and noncovalent reaction whereby beta-face methyl addition to the DELTA24-bond and deprotonation of C-28 proceed to give rise to a nucleophilic rearrangement in which H-24 migrates to C-25 on the reface of the substrate double bond in concert with the initial ionization to afford the bound fecosterol
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
C4-demethyl sterols with double bonds in the nucleus at positions 8, 7, or 5 are acceptable substrates
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
-
zymosterol is 5alpha-cholesta-8,24-dien-3beta-ol
-
-
?
additional information
?
-
enzyme catalyzes a sterol methylation pathway by the algal DELTA25(27)-olefin route, where methylation proceeds by a conserved SN2 reaction and de-protonation proceeds from the pro-Z methyl group on lanosterol corresponding to C27
-
-
?
additional information
?
-
enzyme catalyzes both the reactions of EC 2.1.1.142, cycloartenol 24-C-methyltransferase and EC 2.1.1.143, 24-methylenesterol C-methyltransferase. SMT1 catalyzes a sterol methylation pathway by the algal Delta25(27)-olefin route, where methylation proceeds by a conserved SN2 reaction and deprotonation proceeds from the pro-Z methyl group on lanosterol corresponding to C27
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-
additional information
?
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-
eburicol and obtusifoliol are no substrates
-
-
?
additional information
?
-
-
eburicol and obtusifoliol are no substrates
-
-
?
additional information
?
-
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enzyme involved in biosynthesis of ergosterol, which is a target molecule of leishmanicidal and fungicidal amphotericin B, used for vaccine development
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?
additional information
?
-
enzyme involved in biosynthesis of ergosterol, which is a target molecule of leishmanicidal and fungicidal amphotericin B, used for vaccine development
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?
additional information
?
-
enzyme transfers either one or two methyl groups to the C-24 position of the sterol side chain producing both C28 and C29 24-alkylsterols in approximately the same proportions
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-
?
additional information
?
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enzyme transfers either one or two methyl groups to the C-24 position of the sterol side chain producing both C28 and C29 24-alkylsterols in approximately the same proportions
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?
additional information
?
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overview about a large number of sterol substrates of various origin, substrate specificity analysis, structures: overview
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?
additional information
?
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minimum requirements for productive binding and formation of catalytically active enzyme-substrate complex must be a substrate that possesses a 3beta-hydroxy group, a planar nucleus, an intact side chain that retains the length of the native substrate zymosterol, a 20-R configuration and a delta24-double bond
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-
?
additional information
?
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formation of the ergostane (C1-transfer activity) and stigmastane (C2-transfer activity) sterol side chains, stepwise mutagenesis of amino acids of Erg6p, identification of five residues within the putative active site that contribute directly to C-methylation pathways operated by fungal and plant SMT proteins
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-
?
additional information
?
-
formation of the ergostane (C1-transfer activity) and stigmastane (C2-transfer activity) sterol side chains, stepwise mutagenesis of amino acids of Erg6p, identification of five residues within the putative active site that contribute directly to C-methylation pathways operated by fungal and plant SMT proteins
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?
additional information
?
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-
neither lanosterol nor other C4-methyl-containing sterols bind productively to the enzyme
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-
?