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Literature summary for 2.1.1.142 extracted from

  • 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 (2013), Biochem. J., 456, 253-262.
    View publication on PubMed
Search for more literature for 2.1.1.142

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli Glycine max

Inhibitors

Inhibitors Comment Organism Structure
26-difluorocycloartenol competitive inhibitor Glycine max
26-fluorocycloartenol competitive inhibitor Glycine max

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.031
-
 Cycloartenol pH 7.5, 35°C Glycine max
0.031
-
 Cycloartenol at 35°C in phosphate buffer at pH 8.0 Glycine max
0.036
-
 26-fluorocycloartenol pH 7.5, 35°C Glycine max
0.036
-
 26-fluorocycloartenol at 35°C in phosphate buffer at pH 8.0 Glycine max
0.044
-
 26-difluorocycloartenol pH 7.5, 35°C Glycine max
0.044
-
 26-difluorocycloartenol at 35°C in phosphate buffer at pH 8.0 Glycine max

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-adenosyl-L-methionine + cycloartenol Glycine max
-
 S-adenosyl-L-homocysteine + 24(28)-methylenecycloartanol
-
 ?

Organism

Organism UniProt Comment Textmining
Glycine max
-
-
-

Purification (Commentary)

Purification (Comment) Organism
Q-Sepharose column chromatography Glycine max

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(3beta,13alpha,17alpha)-3-fluorolanost-8,24-diene + S-adenosyl-L-methionine
-
 Glycine max (3beta,13alpha,17alpha)-3-fluoro-24-methylidenelanost-8-ene + S-adenosyl-L-homocysteine conversion into a single 24(28)-methylene product ?
26-difluorocycloartenol + S-adenosyl-L-methionine
-
 Glycine max 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 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 Glycine max ? + S-adenosyl-L-homocysteine hydrolysis of the product gives 26-fluoro-25-hydroxy-24-methylcycloartanol ?
26-homocycloartenol + S-adenosyl-L-methionine
-
 Glycine max 24-methylene-26-homocycloartenol + S-adenosyl-L-homocysteine single product ?
cycloartenol + S-adenosyl-L-methionine
-
 Glycine max 24-methylenecycloartanol + S-adenosyl-L-homocysteine single product ?
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 Glycine max ?
-
 ?
S-adenosyl-L-methionine + 26-difluorocycloartenol
-
 Glycine max ?
-
 ?
S-adenosyl-L-methionine + 26-fluorocycloartenol
-
 Glycine max ?
-
 ?
S-adenosyl-L-methionine + cycloartenol
-
 Glycine max S-adenosyl-L-homocysteine + 24(28)-methylenecycloartanol
-
 ?
S-adenosyl-L-methionine + lanosterol
-
 Glycine max ?
-
 ?

Synonyms

Synonyms Comment Organism
24-SMT
-
 Glycine max
C-24-methyltransferase
-
 Glycine max
SMT1
-
 Glycine max
sterol C-24-methyltransferase
-
 Glycine max

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.071
-
 26-fluorocycloartenol pH 7.5, 35°C Glycine max
0.071
-
 26-fluorocycloartenol at 35°C in phosphate buffer at pH 8.0 Glycine max
0.093
-
 26-difluorocycloartenol pH 7.5, 35°C Glycine max
0.093
-
 26-difluorocycloartenol at 35°C in phosphate buffer at pH 8.0 Glycine max