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Literature summary for 2.1.1.142 extracted from
- Sterol C24-methyltransferase: Mechanistic studies of the C-methylation reaction with 24-fluorocycloartenol (2008), Bioorg. Med. Chem. Lett., 18, 232-235.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expressed in Escherichia coli | Glycine max |
| expressed in Escherichia coli, critical 24H replaced by a fluorine atome | Glycine max |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 24-bromocycloartenol | competitive; competitive inhibitor relative to cycloartenol; time-dependent inhibition kinetics | Glycine max |  |
| 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 | Glycine max | |
| 24-thiacycloartenol | - |
Glycine max | |
| 26,27-dehydrocycloartenol | - |
Glycine max | |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.03 | - |
24-fluorocycloartenol | pH 7.5, 35°C | Glycine max | |
| 0.033 | - |
24-fluorocycloartenol | - |
Glycine max | |
| 0.033 | - |
24-fluorocycloartenol | kinetic mechanism shown | Glycine max | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| microsome | - |
Glycine max | - |
- |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Mg2+ | - |
Glycine max | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| cycloartenol + S-adenosyl-L-methionine | Glycine max | - |
(24S)-24-methylcycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine | - |
? | |
| S-adenosyl-L-methionine + cycloartenol | Glycine max | - |
S-adenosyl-L-homocysteine + 24-methylenecycloartanol | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Glycine max | - |
- |
- |
| Glycine max | - |
isozyme SMT1 | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| partially purified | Glycine max |
| SDS-PAGE | Glycine max |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| culture supernatant | heterologously expressed in Escherichia coli | Glycine max | - |
Specific Activity [micromol/min/mg]
| Specific Activity Minimum [µmol/min/mg] | Specific Activity Maximum [µmol/min/mg] | Comment | Organism |
|---|---|---|---|
| additional information | - |
synthesis and kinetic analysis of the fluorinated substrate analog 24-fluorocycloartenol, electron-withdrawing alpha-fluorine substituent suppresses the rate of the C-methylation reaction by one order of magnitude, critical hydride shift of H24 to C25 to afford time-dependent enzyme inactivation prevented by analyzed substrate analog | Glycine max |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 24-fluorocycloartenol + S-adenosyl-L-methionine | allylic substrate analog | Glycine max | (24R)-24-methyl-24-fluoro-cycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine | - |
? | |
| cycloartenol + S-adenosyl-L-methionine | - |
Glycine max | (24S)-24-methylcycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine | - |
? | |
| S-adenosyl-L-methionine + 24-fluorocycloartenol | - |
Glycine max | S-adenosyl-L-homocysteine + ? | - |
? | |
| S-adenosyl-L-methionine + cycloartenol | - |
Glycine max | S-adenosyl-L-homocysteine + 24-methylenecycloartanol | - |
? | |
| S-adenosyl-L-methionine + 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 | Glycine max | S-adenosyl-L-homocysteine + 24-methylenecycloartanol | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| SMT | - |
Glycine max |
| SMT protein | - |
Glycine max |
| SMT1 | - |
Glycine max |
| sterol 24-C methyltransferase | - |
Glycine max |
| sterol C-24 methyltransferase | - |
Glycine max |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 35 | - |
assay at | Glycine max |
| 35 | - |
inhibition assay at | Glycine max |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0003 | - |
24-fluorocycloartenol | pH 7.5, 35°C | Glycine max | |
| 0.00033 | - |
24-fluorocycloartenol | - |
Glycine max | |
| 0.01 | - |
Cycloartenol | pH 7.5, 35°C | Glycine max | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.5 | - |
assay at | Glycine max |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| S-adenosyl-L-methionine | - |
Glycine max | |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | inhibition kinetics, overview | Glycine max | |
| 0.032 | - |
24-fluorocycloartenol | competitive inhibition, concentration of substrate analogs varied at 5, 15, 25, and 50 microM | Glycine max | |
| 0.032 | - |
24-fluorocycloartenol | pH 7.5, 35°C, versus cycloartenol | Glycine max | |
| 0.036 | - |
24-bromocycloartenol | - |
Glycine max | |
| 0.036 | - |
24-bromocycloartenol | competitive inhibition, concentration of substrate analogs varied at 5, 15, 25, and 50 microM | Glycine max | |
| 0.036 | - |
24-bromocycloartenol | pH 7.5, 35°C, versus cycloartenol | Glycine max | |
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