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24(28)-methylene lophenol + S-adenosyl-L-methionine
24(28)Z-ethylidene lophenol + S-adenosyl-L-homocysteine
-
-
-
?
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-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
-
-
-
-
?
31-norcycloartenol + S-adenosyl-L-methionine
?
-
-
-
-
?
4alpha-methylfecosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
4alpha-methylzymosterol + S-adenosyl-L-methionine
?
-
-
-
-
?
cholest-7,24-dienol + S-adenosyl-L-methionine
?
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
(24R)-24-methylcycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24(28)-methylenecycloartenol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartenol + S-adenosyl-L-homocysteine
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
?
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
-
-
?
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)-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 enzymeāsubstrate 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 + 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 + 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-methylene cycloartenol
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylenecycloartenol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
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 + ?
S-adenosyl-L-methionine + parkeol
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + zymosterol
S-adenosyl-L-homocysteine + ?
zymosterol + S-adenosyl-L-methionine
fecosterol + S-adenosyl-L-homocysteine
24(28)-methylenelophenol + S-adenosyl-L-methionine
additional information
-
cycloartenol + S-adenosyl-L-methionine

24-methylenecycloartenol + S-adenosyl-L-homocysteine
-
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartenol + 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-methylenecycloartenol + S-adenosyl-L-homocysteine
-
-
-
?
cycloartenol + S-adenosyl-L-methionine
24-methylenecycloartenol + S-adenosyl-L-homocysteine
64% of the effectiveness with 24(28)-methylene lophenol
-
-
?
desmosterol + S-adenosyl-L-methionine

?
-
-
-
-
?
desmosterol + S-adenosyl-L-methionine
?
-
-
-
-
-
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-methylene cycloartenol
-
-
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylene cycloartenol
-
active-site topography and reaction mechanisms analyzed with substrate analogs
-
-
?
S-adenosyl-L-methionine + cycloartenol
S-adenosyl-L-homocysteine + 24-methylene cycloartenol
-
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 + ?
-
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 + 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 + ?
-
-
-
-
?
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 + ?
-
-
-
-
?
zymosterol + S-adenosyl-L-methionine

fecosterol + S-adenosyl-L-homocysteine
-
-
-
-
?
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
?
-
-
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
?
-
-
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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(3beta24R,S)-24-methyl-24-thionacycloart-3-ol iodide
-
reversible, non-competitive-type
24(28)-methylene cycloartanol
; competitive
24(28)-methylenecycloartanol
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-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-9,19-cyclolanost-24-en-3-ol
-
i.e. cyclobranol, competitive
24beta-methylcycloartanol
-
competitive with cycloartenol
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
-
-
-
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
-
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0.000055
(3beta24R,S)-24-methyl-24-thionacycloart-3-ol iodide
-
-
0.009 - 0.25
24(28)-methylene cycloartanol
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
0.036
24-bromocycloartenol
-
; competitive inhibition, concentration of substrate analogs varied at 5, 15, 25, and 50 microM; pH 7.5, 35°C, versus cycloartenol
0.042
24-dehydrocycloartenol
-
pH 7.5, 35°C, recombinant enzyme
0.032
24-fluorocycloartenol
-
competitive inhibition, concentration of substrate analogs varied at 5, 15, 25, and 50 microM; pH 7.5, 35°C, versus cycloartenol
0.025
24-methyl-9,19-cyclolanost-24-en-3-ol
-
-
0.002
24-thiacycloartanol
0.15
24beta-methylcycloartanol
-
pH 7.4, 35°C, substrate cycloartenol
0.00001 - 0.00002
25-azacycloartanol
0.00002 - 0.00004
25-Azacycloartenol
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
-
at 35°C in phosphate buffer at pH 8.0
-
0.071
26-fluorocycloartenol
-
at 35°C in phosphate buffer at pH 8.0
-
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
additional information
additional information
-
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
0.002
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
0.00002
25-Azacycloartenol

-
pH 7.5, 35°C, substrate: cycloartenol
0.00004
25-Azacycloartenol
-
inhibition versus cycloartenol
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
0.1
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

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inhibition kinetics, overview
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additional information
additional information
-
inhibition kinetics, overview
-
additional information
additional information
-
inhibition kinetics, overview
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Mangla, A.T.; Nes, W.D.
Sterol C-methyl transferase from Prototheca wickerhamii mechanism, sterol specificity and inhibition
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Prototheca wickerhamii
brenda
Zhou, W.; Nes, W.D.
Sterol methyltransferase2: purification, properties, and inhibition
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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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2003
Glycine max
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Zhou, W.; Song, Z.; Kanagasabai, R.; Liu, J.; Jayasimha, P.; Sinha, A.; Veeramachanemi, P.; Miller, M.B.; Nes, W.D.
Mechanism-based enzyme inactivators of phytosterol biosynthesis
Molecules
9
185-203
2004
Glycine max
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Zhou, W.; Song, Z.; Liu, J.; Miller, M.B.; Nes, W.D.
24-Thiacycloartanol, a potent mechanism-based inactivator of plant sterol methyltransferase
Tetrahedron Lett.
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875-878
2004
Glycine max
-
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Nes, W.D.; Sinha, A.; Jayasimha, P.; Zhou, W.; Song, Z.; Dennis, A.L.
Probing the sterol binding site of soybean sterol methyltransferase by site-directed mutagenesis: functional analysis of conserved aromatic amino acids in Region 1
Arch. Biochem. Biophys.
448
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2006
Glycine max
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Song, Z.; Nes, W.D.
Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26
Bioorg. Med. Chem. Lett.
17
5902-5906
2007
Glycine max
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Wang, J.; Liu, J.; Song, Z.; Nes, W.D.
Sterol C24-methyltransferase: Mechanistic studies of the C-methylation reaction with 24-fluorocycloartenol
Bioorg. Med. Chem. Lett.
18
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2008
Glycine max
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Wang, J.; Nes, W.D.
Cyclobranol: a substrate for C25-methyl sterol side chains and potent mechanism-based inactivator of plant sterol methyltransferase
Bioorg. Med. Chem. Lett.
18
3878-3881
2008
Glycine max
brenda
Neelakandan, A.K.; Song, Z.; Wang, J.; Richards, M.H.; Wu, X.; Valliyodan, B.; Nguyen, H.T.; Nes, W.D.
Cloning, functional expression and phylogenetic analysis of plant sterol 24C-methyltransferases involved in sitosterol biosynthesis
Phytochemistry
70
1982-1998
2009
Glycine max (D2D5G4), Glycine max
brenda
Pereira, M.; Song, Z.; Santos-Silva, L.K.; Richards, M.H.; Nguyen, T.T.; Liu, J.; de Almeida Soares, C.M.; da Silva Cruz, A.H.; Ganapathy, K.; Nes, W.D.
Cloning, mechanistic and functional analysis of a fungal sterol C24-methyltransferase implicated in brassicasterol biosynthesis
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1801
1163-1174
2010
Paracoccidioides brasiliensis, Paracoccidioides brasiliensis Pb0, ATCC MYA-826
brenda
Patkar, P.; Haubrich, B.A.; Qi, M.; Nguyen, T.T.; Thomas, C.D.; Nes, W.D.
C-24-methylation of 26-fluorocycloartenols by recombinant sterol C-24-methyltransferase from soybean: evidence for channel switching and its phylogenetic implications
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456
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2013
Glycine max
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Neelakandan, A.; Chamala, S.; Valliyodan, B.; Nes, W.; Nguyen, H.
Metabolic engineering of soybean affords improved phytosterol seed traits
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10
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2012
Glycine max (Q43445)
brenda