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(3beta,13alpha,17alpha)-3-fluorolanost-8,24-diene + S-adenosyl-L-methionine
(3beta,13alpha,17alpha)-3-fluoro-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine
-
-
conversion into a single 24(28)-methylene product
-
?
14alpha-methylzymosterol + S-adenosyl-L-methionine
14alpha-methyl-24-methylenezymosterol + S-adenosyl-L-homocysteine
-
14alpha-methylzymosterol is 14alpha-methylcholesta-8,24-dien-3beta-ol
-
-
?
24(28)-methylene lophenol + S-adenosyl-L-methionine
24(28)Z-ethylidene lophenol + S-adenosyl-L-homocysteine
-
-
-
?
24(28)-methylene lophenol + S-adenosyl-L-methionine
?
24(28)-methylenecholest-7-enol + S-adenosyl-L-methionine
?
-
-
-
-
?
24(28)-methylenecholesterol + S-adenosyl-L-methionine
?
-
-
-
-
?
24(28)-methylenecycloartanol + S-adenosyl-L-methionine
?
-
-
-
-
?
24(28)-methylenelanosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
24,25-dehydro-27-methenyl-cycloartenol + S-adenosyl-L-methionine
?
-
CA-8, i.e. cycloartenol nucleus substrate analogue with double bond at C8, an enzyme inhibitor, is a poor substrate
-
-
?
24,25-dehydro-27-methylene-cycloartenol + S-adenosyl-L-methionine
?
-
CA-14, i.e. cycloartenol nucleus substrate analogue with double bond at C14, an enzyme inhibitor, is a poor substrate
-
-
?
24,25-dehydropollinastanol + S-adenosyl-L-methionine
?
-
24,25-dehydropollinastanol is 14alpha-methyl-9beta,19-cyclo-5alpha-cholest-24-en-3beta-ol
-
-
?
24-fluorocycloartenol + S-adenosyl-L-methionine
(24R)-24-methyl-24-fluoro-cycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine
-
allylic substrate analog
-
-
?
26,27-dehydrozymosterol + S-adenosyl-L-methionine
26-homocholesta-8(9),23(24)E,26(26')-trienol + 26-homocholesta-8(9),26(26')-3beta,24beta-dienol
-
-
-
-
?
26-difluorocycloartenol + S-adenosyl-L-methionine
26-difluoro-25-hydroxy-24-methylcycloartanol + S-adenosyl-L-homocysteine
-
-
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
-
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
-
?
26-homocycloartenol + S-adenosyl-L-methionine
24-methylene-26-homocycloartenol + S-adenosyl-L-homocysteine
-
-
single product
-
?
31-norcycloartenol + S-adenosyl-L-methionine
24-methylene-31-norcycloartenol + S-adenosyl-L-homocysteine
-
31-norcycloartenol is 4,14alpha-dimethyl-9beta,19-cyclo-5alpha-cholest-24-en-3beta-ol
-
-
?
31-norcycloartenol + S-adenosyl-L-methionine
?
-
-
-
-
?
4alpha-methylfecosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
4alpha-methylzymosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
agnosterol + S-adenosyl-L-methionine
24-methyleneagnosterol + S-adenosyl-L-homocysteine
-
agnosterol is 4,4,14alpha-trimethyl-5alpha-cholesta-7(8),9(11),24-trien-3beta-ol
-
-
?
cholest-7,24-dienol + S-adenosyl-L-methionine
?
-
-
-
-
?
cholesta-5,7,24-trienol + S-adenosyl-L-methionine
?
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
(24S)-24-methylcycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylene cycloartanol + S-adenosyl-L-homocysteine
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
cycloartenol 3-ketone + S-adenosyl-L-methionine
?
-
cycloartenol 3-ketone is 4,4,14alpha-trimethyl-9beta,19-cyclo-5alpha-cholest-24-en-3-one
-
-
?
cyclobranol + S-adenosyl-L-methionine
9beta-25-methylidene-9,19-cyclolanost-1-ene-1,3-diol + S-adenosyl-L-homocysteine
-
-
-
-
?
dehydropollinastanol + S-adenosyl-L-methionine
?
-
-
-
-
?
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
?
ergosta-7,24(28)-dienol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
fecosterol and ergosta-7,24(28)-dienol which lack C4-and C14-methyl groups in the nucleus are catalyzed equally effectively by SMT2-2 as the natural substrate 24(28)-methylene lophenol
-
-
?
fecosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
fecosterol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
fecosterol and ergosta-7,24(28)-dienol which lack C4-and C14-methyl groups in the nucleus are catalyzed equally effectively by SMT2-2 as the natural substrate 24(28)-methylene lophenol
-
-
?
lanost-24-enol + S-adenosyl-L-methionine
24-methylene-lanost-24-erol + S-adenosyl-L-homocysteine
-
lanost-24-enol is 4,4,14alpha-trimethyl-5alpha-cholesta-9(11),24-dien-3beta-ol
-
-
?
lanosta-7,24-dienol + S-adenosyl-L-methionine
24-methylene-lanost-7,24-dienol + S-adenosyl-L-homocysteine
-
lanosta-7,24-dienol is 4,4,14alpha-trimethyl-5alpha-cholesta-7(8),24-dien-3beta-ol
-
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
lanosterol + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
-
-
-
?
obtusifoliol + S-adenosyl-L-methionine
?
-
-
-
-
?
S-adenosyl-L-methionine + 14-methylzymosterol
?
-
-
-
-
?
S-adenosyl-L-methionine + 14alpha-methylzymosterol
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 + 24(28)-methylenecycloartanol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 24(28)-methylenelanosterol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 24(28)-methylenelophenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 24-dehydropollinstanol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 24-fluorocycloartenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 24-methyl-9,19-cyclolanost-24-en-3-ol
S-adenosyl-L-homocysteine + 25-methyl-24-methylidene-9,19-cyclolanostan-3-ol
-
i.e. cyclobranol
-
-
?
S-adenosyl-L-methionine + 26,27-dehydrocycloartenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 26,27-dehydrolanosterol
?
-
Formation of a reversibly bound enzymesubstrate complex, followed by catalysis to an intermediate that can be converted to a methyl product or the intermediate can be intercepted through covalent modification and hence irreversible inhibition, lanosterol or 26,27-dehydrolanosterol can lead to distinct intermediates that convert to methylated sterol products
-
-
?
S-adenosyl-L-methionine + 26-difluorocycloartenol
?
-
-
-
-
?
S-adenosyl-L-methionine + 26-fluorocycloartenol
?
-
-
-
-
?
S-adenosyl-L-methionine + 30,31-dinorcycloartenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 31-norcycloartenol
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + 31-norlanosterol
?
-
-
-
-
?
S-adenosyl-L-methionine + 5alpha-cholesta-8,24-dien-3beta-ol
S-adenosyl-L-homocysteine + 24-methylene-5alpha-cholest-8-en-3beta-ol
-
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
-
-
?
S-adenosyl-L-methionine + cholesta-5,20(22)E,24-trienol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + cholesta-5,7,22E,24-tetraenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + cholesta-5,7,24-trienol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + cholesta-7,24-dienol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + (24R)-24-methylcycloart-25-en-3beta-ol
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24(28)-methylenecycloartanol
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24(28)methylene cycloartanol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartanol
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol + 24(28)-methylene cycloartanol
-
-
-
?
S-adenosyl-L-methionine + desmosterol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + lanosterol
?
-
-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24beta-methyl lanosta-8,25(27)-enol + 24(28)-methylene lanosterol
-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + obtusifoliol
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + parkeol
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
24(28)-methylenelophenol + S-adenosyl-L-methionine
additional information
-
24(28)-methylene lophenol + S-adenosyl-L-methionine
?
-
-
-
-
?
24(28)-methylene lophenol + S-adenosyl-L-methionine
?
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylene cycloartanol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylene cycloartanol + S-adenosyl-L-homocysteine
optimal substrate for SMT1
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
SMT2 has a position-specific substrate specificity for DELTA24(25)-sterols and contains a single active center to catalyze the consecutive C1-transfer activities by substrate reaction channels similar to the fungal SMT1
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
single product
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
rate-limiting initial step in the conversion of phytosterol
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
64% of the effectiveness with 24(28)-methylene lophenol
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
cycloartenol is 4,4,14alpha-trimethyl-9beta,19-cyclo-5alpha-cholest-24-en-3beta-ol
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartanol + S-adenosyl-L-homocysteine
-
cycloartenol is 4,4,14alpha-trimethyl-9beta,19-cyclo-5alpha-cholest-24-en-3beta-ol
-
-
?
desmosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
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
-
?
lanosterol + S-adenosyl-L-methionine
24-methylene-24,25-dihydrolanosterol + S-adenosyl-L-homocysteine
-
regiospecific
-
-
?
S-adenosyl-L-methionine + 31-norcycloartenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 31-norcycloartenol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + (24R)-24-methylcycloart-25-en-3beta-ol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + (24R)-24-methylcycloart-25-en-3beta-ol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + (24R)-24-methylcycloart-25-en-3beta-ol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + (24R)-24-methylcycloart-25-en-3beta-ol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24(28)-methylenecycloartanol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24(28)-methylenecycloartanol
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartanol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartanol
-
active-site topography and reaction mechanisms analyzed with substrate analogs
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartanol
-
fluorine-modified sterol side chains designed to examine the electrophilic nature of the common C-methylation reaction affecting C1 and C2-activities, might retard C-methylation reaction to afford protein alkylation
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartanol
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + ?
-
successive C-methylations of the DELTA24 bond occurs at the same active center. The two methylation steps can proceed by a change in chemical mechanism resulting from differences in sterol structure, concerted versus carbocation. The kinetic mechanism remains the same during the consecutive methylation of the DELTA24 bond
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + ?
-
the first C1-transfer is 24(28) methylenecycloartenol, SN2-type and non-stop, ternary complex mechanism. The second C1-transfer is a mixture of 24-ethyl olefins, SN2-type and step-wise. Ordered pathway with S-adenosyl-L-methionine binding first
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + cyclolaudenol
-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
-
PbSMT synthesizes a single product, eburicol 24(28)-methylene-24,25-dihydro-lanosterol, from lanosterol
i.e. eburicol
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
-
PbSMT catalysis of the sterol acceptor lead to a C24-methyl product in which the 1,2-hydride migration of C24 to C25 occurs specifically from the Re-face of the original substrate double bond undergoing transalkylation
i.e. eburicol
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
-
PbSMT synthesizes a single product, eburicol 24(28)-methylene-24,25-dihydro-lanosterol, from lanosterol
i.e. eburicol
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
-
PbSMT catalysis of the sterol acceptor lead to a C24-methyl product in which the 1,2-hydride migration of C24 to C25 occurs specifically from the Re-face of the original substrate double bond undergoing transalkylation
i.e. eburicol
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + 24(28)-methylene-24,25-dihydro-lanosterol
-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + lanosterol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + parkeol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + parkeol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
-
-
-
?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + fecosterol
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
24(28)-methylenelophenol + S-adenosyl-L-methionine
additional information
-
-
-
a mixture of three stereochemical related products with DELTA24(28)Z-ethylidene, DELTA24(28)-ethylidene and DELTA25(27)-24beta-ethyl side chains
-
?
additional information
?
-
-
no activity with cycloartanol, 3-deoxycycloartenol, or cyclolaudenol
-
-
?
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
-
-
-
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
-
-
-
additional information
?
-
-
the SMT from soybean plants is bifunctional, performing methyl transferations to C24 and to C28 of the substrate, the enzyme also converts the inhibitor 24,25-dehydro-27-methenyl-cycloartenol, i.e. cycloartenol nucleus substrate analogue with double bond at C8, to a 24,27-dimethenyl-cycloartenol, CA-11, compound, overview
-
-
?
additional information
?
-
-
achieving the cyclolaudenyl cation intermediate by electrophilic alkylation of cycloartenol is significant to the overall reaction rate. The evolution of variant sterol C-24-methylation patterns is driven by competing reaction channels that have switched in algae from formation of primarily DELTA25(27) products that convert into ergosterol to, in land plants, formation of DELTA24(28) products that convert into sitosterol
-
-
?
additional information
?
-
-
GC-MS analysis shows that the fungus synthesizes 12 compounds of which lanosterol, ergosterol and brassicasterol make up approximately 80% of the sterol mixture
-
-
?
additional information
?
-
-
SMT recognition of lanosterol and cycloartenol versus zymosterol is the C3-OH group, whose orientation in the A-ring and hydrogen bonding ability can affect productive binding of the acceptor molecule. The recombinant enzyme expressed in Escherichia coli possesess a substrate specificity for lanosterol and generates a single exocyclic methylene product. Regiospecific conversion of the pro-Z methyl group of the DELTA24(25)-substrate to the pro-R isopropyl methyl group of the product and the migration of H24 to C25 on the Re-face of the original substrate double bond undergoing C24-methylation, NMR and mass spectrometric analysis, overview. No activity with 24(28)-methylenelophenol, fecosterol, or eburicol
-
-
?
additional information
?
-
-
GC-MS analysis shows that the fungus synthesizes 12 compounds of which lanosterol, ergosterol and brassicasterol make up approximately 80% of the sterol mixture
-
-
?
additional information
?
-
-
SMT recognition of lanosterol and cycloartenol versus zymosterol is the C3-OH group, whose orientation in the A-ring and hydrogen bonding ability can affect productive binding of the acceptor molecule. The recombinant enzyme expressed in Escherichia coli possesess a substrate specificity for lanosterol and generates a single exocyclic methylene product. Regiospecific conversion of the pro-Z methyl group of the DELTA24(25)-substrate to the pro-R isopropyl methyl group of the product and the migration of H24 to C25 on the Re-face of the original substrate double bond undergoing C24-methylation, NMR and mass spectrometric analysis, overview. No activity with 24(28)-methylenelophenol, fecosterol, or eburicol
-
-
?
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(24R)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
-
-
(24R)-24-methyl-25-azacycloartenol
-
-
(24R,S)-24-Ethyl-25-azacycloartenol
-
-
(24R,S)-24-Methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
-
-
(24R,S)-24-Methyl-25,26,27-trisnor-24-dimethylsulfonium cycloartenol iodide
-
-
(24R,S)-24-Methyl-25,26,27-trisnor-24-trimethylarsonium cycloartenol iodide
-
-
(24R,S)-24-Methyl-25-azacycloartenol
-
-
(24S)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
-
-
(24S)-24-methyl-25-azacycloartenol
-
-
(3beta24R,S)-24-methyl-24-thionacycloart-3-ol iodide
-
reversible, non-competitive-type
24(28)-methylene cycloartanol
competitive
24(28)-methylenecycloartanol
24(28)-methylenecycloartenol
-
-
24(28)-methylenencycloartanol
-
-
24,25-dehydro-27-methenyl-cycloartenol
-
i.e. cycloartenol nucleus substrate analogue with double bond at C8
24,25-dehydro-27-methylene-cycloartenol
-
i.e. cycloartenol nucleus substrate analogue with double bond at C14, non-competitive
24-Azacycloartanyl acetate
-
-
24-bromocycloartenol
-
competitive; competitive inhibitor relative to cycloartenol; time-dependent inhibition kinetics
24-dehydrocycloartenol
-
a mechanism-based inactivator
24-fluorocycloartenol
-
allylic substrate analog, time-dependent inhibition kinetics, consistent with the action of a suicide substrate that irreversibly inactivates the enzyme; competitive, the electron-withdrawing alpha-fluorine substituent suppresses the rate of the C-methylation reaction
24-Methyl-25,26,27-trisnor-24-trimethylammonium cycloartenol iodide
-
24R and 24S isomer
24-Methyl-25-azacycloartenol
-
24R and 24S isomer
24-methyl-9,19-cyclolanost-24-en-3-ol
-
i.e. cyclobranol, competitive
24-Oxo-25-azacycloartenol
-
-
24beta-methylcycloartanol
-
competitive with cycloartenol
25,26,27-Trisnor-24-trimethylammonium cycloartenol iodide
-
-
25-azacycloartanol
non-competitive
25-azalanosterol
-
substrate analogue, competitive-type inhibitor, a potent inhibitor of cell growth promoting lanosterol accumulation and 24-alkyl sterol depletion
26,27-dehydrocycloartenol
-
-
26,27-dehydrolanosterol
-
substrate analogue, competitive-type inhibitor, pseudofirst-order, time-dependent inactivation of the PbSMT. Formation of a reversibly bound enzyme-substrate complex, followed by catalysis to an intermediate that can be converted to a methyl product or the intermediate can be intercepted through covalent modification and hence irreversible inhibition, lanosterol or 26,27-dehydrolanosterol can lead to distinct intermediates that convert to methylated sterol products
26,27-dehydrozymosterol
-
mechanism-based inhibitor, specific covalent modification of SMT2
26-difluorocycloartenol
-
competitive inhibitor
26-fluorocycloartenol
-
competitive inhibitor
26-methenylcycloartenol
-
pseudo-first-order time-dependent inactivation, less potency of inhibition
26-methynylcycloartenol
-
inhibition kinetics non-competitive and time-dependent, less potency of inhibition
citrostadienol
-
competitive with cycloartenol or 24(28)-methylenelophenol
cycloarta-24,26-dienol
-
-
cyclobranol
-
competitive-type inhibitor
cyclolaudenol
-
dead end inhibitor analog, competitive versus cycloartenol, uncompetitive versus S-adenosyl-L-methionine
S-adenosyl-L-homocysteine
-
noncompetitive with respect to S-adenosyl-L-methionine
24(28)-methylenecycloartanol
-
competitive with cycloartenol
24(28)-methylenecycloartanol
-
competitive with respect to S-adenosyl-L-methionine
24-thiacycloartanol
-
irreversible
24-thiacycloartanol
-
a mechanism-based inactivator
25-Azacycloartenol
-
competitive with cycloartenol or 24(28)-methylenelophenol; noncompetitive
25-Azacycloartenol
-
noncompetitive inhibitor versus cycloartenol, uncompetitive inhibitor versus S-adenosyl-L-methionine
sitosterol
-
competitive with cycloartenol or 24(28)-methylenelophenol
additional information
-
neither ergosterol or cholesterol inhibit activity
-
additional information
-
non-competitive inhibitors are ammonium group substituted for carbon at C25, C24, C23 and C22; overview, diverse substrate and transition state analogues
-
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0.000015
(24R)-24-methyl-25,26,27-trisnor-24-dimethylamino-N-oxide cycloartenol
-
-
0.00002
(24R)-24-methyl-25-azacycloartenol
-
-
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
-
-
0.000055
(3beta24R,S)-24-methyl-24-thionacycloart-3-ol iodide
-
-
0.00009
23-Azacholesterol
-
-
0.00009 - 0.25
24(28)-methylene cycloartanol
0.085
24(28)-methylenecycloartenol
-
-
0.171
24(28)-methylenencycloartanol
-
-
0.047
24,25-dehydro-27-methenyl-cycloartenol
-
pH 7.5, 35°C, recombinant enzyme
0.067
24,25-dehydro-27-methylene-cycloartenol
-
pH 7.5, 35°C, recombinant enzyme
0.00018
24-Azacholesterol
-
-
0.00003
24-Azacycloartanyl acetate
-
-
0.036
24-bromocycloartenol
0.042
24-dehydrocycloartenol
-
pH 7.5, 35°C, recombinant enzyme
0.032
24-fluorocycloartenol
0.000035
24-Methyl-25,26,27-trisnor-24-trimethylammonium cycloartenol iodide
-
-
0.025
24-methyl-9,19-cyclolanost-24-en-3-ol
-
-
0.00017
24-Oxo-25-azacycloartenol
-
-
0.002
24-thiacycloartanol
0.15
24beta-methylcycloartanol
-
pH 7.4, 35°C, substrate cycloartenol
0.000035
25,26,27-Trisnor-24-trimethylammonium cycloartenol iodide
-
-
0.000045
25-Azacholesterol
-
-
0.00001 - 0.00002
25-azacycloartanol
0.000002 - 0.0001
25-Azacycloartenol
0.00004
25-azacyloartenol
-
0.000014
25-azalanosterol
-
pH 7.5, 30°C, recombinant wild-type enzyme
0.042
26,27-dehydrocycloartenol
-
-
0.054
26,27-dehydrolanosterol
-
pH 7.5, 30°C, recombinant wild-type enzyme
0.049
26,27-dehydrozymosterol
-
pH 7.5, 35°C
0.093
26-difluorocycloartenol
0.071
26-fluorocycloartenol
0.047
26-methenylcycloartenol
-
rate of inactivation saturable, comparable to values obtained for cycloartenol
0.045 - 0.05
citrostadienol
0.017
cycloarta-24,26-dienol
-
-
0.03
Cycloartenol
-
natural substrate
0.007 - 0.009
cyclolaudenol
0.047 - 0.056
S-adenosyl-L-homocysteine
0.0001 - 0.207
sitosterol
additional information
additional information
-
0.00009
24(28)-methylene cycloartanol
-
0.009
24(28)-methylene cycloartanol
-
inhibition versus S-adenosyl-L-methionine
0.077
24(28)-methylene cycloartanol
substrate cycloartenol
0.116
24(28)-methylene cycloartanol
substrate 24(28)-methylene lophenol
0.171
24(28)-methylene cycloartanol
-
inhibition versus cycloartenol
0.25
24(28)-methylene cycloartanol
-
pH 7.4, 35°C, substrate cycloartenol
0.036
24-bromocycloartenol
-
-
0.036
24-bromocycloartenol
-
competitive inhibition, concentration of substrate analogs varied at 5, 15, 25, and 50 microM
0.036
24-bromocycloartenol
-
pH 7.5, 35°C, versus cycloartenol
0.032
24-fluorocycloartenol
-
competitive inhibition, concentration of substrate analogs varied at 5, 15, 25, and 50 microM
0.032
24-fluorocycloartenol
-
pH 7.5, 35°C, versus cycloartenol
0.002
24-thiacycloartanol
-
-
0.002
24-thiacycloartanol
-
pH 7.5, 35°C, recombinant enzyme
0.00001
25-azacycloartanol
substrate cycloartenol
0.00002
25-azacycloartanol
substrate 24(28)-methylene lophenol
0.000002
25-Azacycloartenol
-
-
0.00002
25-Azacycloartenol
-
pH 7.5, 35°C, substrate: cycloartenol
0.00003
25-Azacycloartenol
-
-
0.00004
25-Azacycloartenol
-
inhibition versus cycloartenol
0.0001
25-Azacycloartenol
-
inhibition versus S-adenosyl-L-methionine
0.093
26-difluorocycloartenol
-
pH 7.5, 35°C
0.093
26-difluorocycloartenol
-
at 35°C in phosphate buffer at pH 8.0
0.071
26-fluorocycloartenol
-
pH 7.5, 35°C
0.071
26-fluorocycloartenol
-
at 35°C in phosphate buffer at pH 8.0
0.045
citrostadienol
-
pH 7.4, 35°C, substrate: 24(28)-methylenelophenol
0.05
citrostadienol
-
pH 7.4, 35°C, substrate cycloartenol
0.007
cyclolaudenol
-
inhibition versus cycloartenol
0.009
cyclolaudenol
-
inhibition versus S-adenosyl-L-methionine
0.047
S-adenosyl-L-homocysteine
-
inhibition versus cycloartenol
0.056
S-adenosyl-L-homocysteine
-
inhibition versus S-adenosyl-L-methionine
0.0001
sitosterol
-
0.1
sitosterol
substrate cycloartenol
0.154
sitosterol
substrate 24(28)-methylene lophenol
0.2
sitosterol
-
pH 7.5, 35°C, substrate: cycloartenol
0.207
sitosterol
-
pH 7.4, 35°C, substrate: 24(28)-methylenelophenol
additional information
additional information
-
overview, diverse substrate and transition state analogues
-
additional information
additional information
-
inhibition kinetics, overview
-
additional information
additional information
-
inhibition kinetics, overview
-
additional information
additional information
-
inhibition kinetics, overview
-
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Sterol C-methyl transferase from Prototheca wickerhamii mechanism, sterol specificity and inhibition
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Prototheca wickerhamii
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Schaeffer, A.; Bronner, R.; Benveniste, P.; Schaller, H.
The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by sterol methyltransferase 2;1
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Arabidopsis thaliana
brenda
Nes, W.D.; Janssen, G.G.; Bergenstrahle, A.
Structural requirements for transformation of substrates by the (S)-adenosyl-L-methionine:delta 24(25)-sterol methyl transferase
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Helianthus annuus
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Rahier, A.; Genot, J.C.; Schuber, F.; Benveniste, P.; Narula, A.S.
Inhibition of S-adenosyl-L-methionine sterol-C-24-methyltransferase by analogues of a carbocationic ion high-energy intermediate. Structure activity relationships for C-25 heteroatoms (N, As, S) substituted triterpenoid derivatives
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1984
Zea mays
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Diener, A.C.; Li, H.; Zhou, W.X.; Whoriskey, W.J.; Nes, W.D.; Fink, G.R.
Sterol methyltransferase 1 controls the level of cholesterol in plants
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12
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2000
Arabidopsis thaliana (Q9LM02)
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Shi, J.; Gonzales, R.A.; Bhattacharyya, M.K.
Identification and characterization of an S-adenosyl-L-methionine:DELTA24-sterol-C-methyltransferase cDNA from soybean
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Glycine max, Glycine max (Q43445)
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Holmberg, N.; Harker, M.; Wallace, A.D.; Clayton, J.C.; Gibbard, C.L.; Safford, R.
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Nicotiana tabacum
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Sterol methyltransferase2: purification, properties, and inhibition
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420
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2003
Arabidopsis thaliana
brenda
Nes, W.D.; Song, Z.; Dennis, A.L.; Zhou, W.; Nam, J.; Miller, M.B.
Biosynthesis of phytosterols. Kinetic mechanism for the enzymatic C-methylation of sterols
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278
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Glycine max
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Mechanism-based enzyme inactivators of phytosterol biosynthesis
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9
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Glycine max
brenda
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24-Thiacycloartanol, a potent mechanism-based inactivator of plant sterol methyltransferase
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45
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Glycine max
-
brenda
Nes, W.D.; Sinha, A.; Jayasimha, P.; Zhou, W.; Song, Z.; Dennis, A.L.
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Glycine max
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Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26
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17
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Glycine max
brenda
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Sterol C24-methyltransferase: Mechanistic studies of the C-methylation reaction with 24-fluorocycloartenol
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18
232-235
2008
Glycine max
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Gossypium hirsutum
brenda
Wang, J.; Nes, W.D.
Cyclobranol: a substrate for C25-methyl sterol side chains and potent mechanism-based inactivator of plant sterol methyltransferase
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18
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2008
Glycine max
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Cloning, functional expression and phylogenetic analysis of plant sterol 24C-methyltransferases involved in sitosterol biosynthesis
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Cloning, mechanistic and functional analysis of a fungal sterol C24-methyltransferase implicated in brassicasterol biosynthesis
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153
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brenda
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brenda
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20
595-604
2018
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brenda
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113
64-72
2015
Chlamydomonas reinhardtii (A8IJ34), Chlamydomonas reinhardtii
brenda
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14
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2018
Naegleria fowleri
brenda
Atsumi, G.; Kagaya, U.; Tabayashi, N.; Matsumura, T.
Analysis of the mechanisms regulating the expression of isoprenoid biosynthesis genes in hydroponically-grown Nicotiana benthamiana plants using virus-induced gene silencing
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8
14804
2018
Nicotiana benthamiana
brenda