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Literature summary for 2.3.1.238 extracted from

  • Xie, X.; Watanabe, K.; Wojcicki, W.A.; Wang, C.C.; Tang, Y.
    Biosynthesis of lovastatin analogs with a broadly specific acyltransferase (2006), Chem. Biol., 13, 1161-1169.
    View publication on PubMed
Search for more literature for 2.3.1.238

Application

Application Comment Organism
synthesis the enzyme can be a useful biocatalyst for the synthesis of simvastatin and other statin analogs. It is an attractive enzyme for engineered biosynthesis of pharmaceutically important cholesterol-lowering drugs Aspergillus terreus

Cloned(Commentary)

Cloned (Comment) Organism
overexpression in Escherichia coli Aspergillus terreus

Protein Variants

Protein Variants Comment Organism
S76A no activity Aspergillus terreus

Inhibitors

Inhibitors Comment Organism Structure
monacolin J competitive inhibitor of butyryl-CoA, substrate inhibition occurs due to binding of monacolin J to the free enzyme, forming a LovD-monacolin J complex and blocking entrance of butyryl-CoA Aspergillus terreus
additional information no substrate inhibition by butyryl-CoA at high concentrations is observed Aspergillus terreus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information Km-value for hydrolysis of lovastain to monacolin J is 0.56 mM Aspergillus terreus
1.59
-
 butyryl-CoA pH 7.9, 25°C Aspergillus terreus

Organism

Organism UniProt Comment Textmining
Aspergillus terreus Q9Y7D1
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Aspergillus terreus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-2-methylbutanoyl-N-acetylcysteamine + 6-hydroxy-6-demethylmonacolin J
-
 Aspergillus terreus pravastatin + N-acetylcysteamine
-
 ?
(S)-2-methylbutanoyl-N-acetylcysteamine + monacolin J
-
 Aspergillus terreus lovastatin + N-acetylcysteamine
-
 ?
alpha-dimethylbutanoyl-N-acetylcysteamine + 6-hydroxy-6-demethylmonacolin J
-
 Aspergillus terreus huvastatin + N-acetylcysteamine
-
 ?
alpha-dimethylbutanoyl-N-acetylcysteamine + monacolin J
-
 Aspergillus terreus simvastatin + N-acetylcysteamine
-
 ?
benzoyl-CoA + monacolin J
-
 Aspergillus terreus ? + CoA
-
 ?
butanoyl-N-acetylcysteamine + monacolin J
-
 Aspergillus terreus (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl butanoate + N-acetylcysteamine
-
 ?
butyryl-CoA + monacolin J 87% conversion after 10 h Aspergillus terreus (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl butanoate + CoA
-
 ?
hexanoyl-N-acetylcysteamine + monacolin J
-
 Aspergillus terreus ? + N-acetylcysteamine
-
 ?
additional information the enzyme displays preference toward medium chain length (C3–C6) acyl groups, with butyryl-CoA being the optimal alkylacyl-CoA substrate. Both acetyl- and octanoyl-CoA are poor substrates of LovD, with less than 10% acylation of monacolin J. The enzyme also catalyzes hydrolysis of lovastain to monacolin J. Butyryl-thioethane and butyryl-thioethanol are not competent substrates of the enzyme Aspergillus terreus ?
-
 ?
pentanoyl-N-acetylcysteamine + monacolin J
-
 Aspergillus terreus ? + N-acetylcysteamine
-
 ?

Synonyms

Synonyms Comment Organism
LovD
-
 Aspergillus terreus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Aspergillus terreus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
additional information
-
 additional information kcat-value for hydrolysis of lovastain to monacolin J is 0.0035/s Aspergillus terreus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.9
-
 assay at Aspergillus terreus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.33
-
 monacolin J pH 7.9, 25°C Aspergillus terreus