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Literature summary for 2.1.1.142 extracted from

  • Song, Z.; Nes, W.D.
    Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26 (2007), Bioorg. Med. Chem. Lett., 17, 5902-5906.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli, recombinant protein Glycine max
expression in Escherichia coli Glycine max

Inhibitors

Inhibitors Comment Organism Structure
24,25-dehydro-27-methenyl-cycloartenol i.e. cycloartenol nucleus substrate analogue with double bond at C8 Glycine max
24,25-dehydro-27-methylene-cycloartenol i.e. cycloartenol nucleus substrate analogue with double bond at C14, non-competitive Glycine max
24-dehydrocycloartenol a mechanism-based inactivator Glycine max
24-thiacycloartanol a mechanism-based inactivator Glycine max
26-methenylcycloartenol pseudo-first-order time-dependent inactivation, less potency of inhibition Glycine max
26-methynylcycloartenol inhibition kinetics non-competitive and time-dependent, less potency of inhibition Glycine max
Cycloartenol
-
Glycine max

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information kinetics, overview Glycine max
0.005
-
24,25-dehydro-27-methylene-cycloartenol pH 7.5, 35°C, recombinant enzyme Glycine max
0.03
-
Cycloartenol pH 7.5, 35°C, recombinant enzyme 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
-
?

Organism

Organism UniProt Comment Textmining
Glycine max
-
-
-

Purification (Commentary)

Purification (Comment) Organism
partially purified, recombinant protein, SDS-PAGE Glycine max
recombinant enzyme from Escherichia coli to homogeneity Glycine max

Source Tissue

Source Tissue Comment Organism Textmining
culture supernatant
-
Glycine max
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
additional information
-
C-methylation reaction analyzed with substrate analogs containing a cycloartenol nucleus and a double bond or triple bond attached to C26, mass spectra of enzyme-generated products indicated, time-dependent inhibition kinetics reveals active-site directed process and partitioning to produce novel products Glycine max

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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 Glycine max ?
-
?
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 Glycine max ?
-
?
cycloartenol + S-adenosyl-L-methionine
-
Glycine max (24S)-24-methylcycloart-25-en-3beta-ol + S-adenosyl-L-homocysteine
-
?
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 Glycine max ?
-
?
S-adenosyl-L-methionine + cycloartenol active-site topography and reaction mechanisms analyzed with substrate analogs Glycine max S-adenosyl-L-homocysteine + 24-methylenecycloartanol
-
?

Synonyms

Synonyms Comment Organism
More the enzyme belongs to a family of sterol 24-C-methyltransferases that perform distinct C1-activities, two different alkylations at C24 or C28, alkylation of the latter affects membrane fluidity Glycine max
SMT
-
Glycine max
SMT protein
-
Glycine max
sterol 24-C 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
0.00000083
-
24,25-dehydro-27-methylene-cycloartenol pH 7.5, 35°C, recombinant enzyme Glycine max
0.01
-
Cycloartenol pH 7.5, 35°C, recombinant enzyme Glycine max

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Glycine max
7.5
-
inhibition 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
0.002
-
24-thiacycloartanol pH 7.5, 35°C, recombinant enzyme Glycine max
0.03
-
Cycloartenol natural substrate Glycine max
0.042
-
24-dehydrocycloartenol pH 7.5, 35°C, recombinant enzyme Glycine max
0.047
-
24,25-dehydro-27-methenyl-cycloartenol pH 7.5, 35°C, recombinant enzyme Glycine max
0.047
-
26-methenylcycloartenol rate of inactivation saturable, comparable to values obtained for cycloartenol Glycine max
0.067
-
24,25-dehydro-27-methylene-cycloartenol pH 7.5, 35°C, recombinant enzyme Glycine max

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.067
-
co-incubation with 50 microM or 100 microM cycloartenol affords protection against inactivation generating 25% and 45% C-methylation Glycine max 26-methynylcycloartenol