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3alpha-hydroxy-3,5-dihydromonacolin L acid = monacolin L acid + H2O
dihydromonacolin L acid + O2 + [reduced NADPH-hemoprotein reductase] = 3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
dihydromonacolin L acid + O2 + [reduced NADPH-hemoprotein reductase] = monacolin L acid + [oxidized NADPH-hemoprotein reductase] + 2 H2O
3alpha-hydroxy-3,5-dihydromonacolin L acid = monacolin L acid + H2O
(1b), spontaneous
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3alpha-hydroxy-3,5-dihydromonacolin L acid = monacolin L acid + H2O
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dihydromonacolin L acid + O2 + [reduced NADPH-hemoprotein reductase] = 3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
(1a)
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dihydromonacolin L acid + O2 + [reduced NADPH-hemoprotein reductase] = 3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
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dihydromonacolin L acid + O2 + [reduced NADPH-hemoprotein reductase] = monacolin L acid + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(overall reaction)
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dihydromonacolin L acid + O2 + [reduced NADPH-hemoprotein reductase] = monacolin L acid + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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3alpha-hydroxy-3,5-dihydromonacolin L acid
monacolin L acid + H2O
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
monacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
3alpha-hydroxy-3,5-dihydromonacolin L acid
monacolin L acid + H2O
spontaneous
(1b), spontaneous
-
?
3alpha-hydroxy-3,5-dihydromonacolin L acid
monacolin L acid + H2O
-
spontaneous
(1b), spontaneous
-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product is unstable und under mildly acidic conditions and elevated temperature, it converts to monacolin L
-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
dihydromonacolin L acid i.e. (3R,5R)-7-[(1S,2S,4aR,6R,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen1yl]-3,5-dihydroxyheptanoate. The enzyme also catalyses the reaction of EC 1.14.14.124, monacolin L hydroxylase. The enzyme is involved in the biosynthesis of lovastatin
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-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
dihydromonacolin L acid i.e. (3R,5R)-7-[(1S,2S,4aR,6R,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen1yl]-3,5-dihydroxyheptanoate. The enzyme also catalyses the reaction of EC 1.14.14.124, monacolin L hydroxylase
-
-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
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dihydromonacolin L acid i.e. (3R,5R)-7-[(1S,2S,4aR,6R,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen1yl]-3,5-dihydroxyheptanoate
-
-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
reaction of cell free extract in presence of air
-
-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
monacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
monacolin L acid i.e. (3R,5R)-7-[(1S,2S,6R,8aR)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate. The enzyme also catalyses the reaction of EC 1.14.13.198, monacolin L hydroxylase
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-
?
dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
monacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
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monacolin L acid i.e. (3R,5R)-7-[(1S,2S,6R,8aR)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
-
-
?
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dihydromonacolin L acid + [reduced NADPH-hemoprotein reductase] + O2
3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH-hemoprotein reductase] + H2O
dihydromonacolin L acid i.e. (3R,5R)-7-[(1S,2S,4aR,6R,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen1yl]-3,5-dihydroxyheptanoate. The enzyme also catalyses the reaction of EC 1.14.14.124, monacolin L hydroxylase. The enzyme is involved in the biosynthesis of lovastatin
-
-
?
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Barriuso, J.; Nguyen, D.T.; Li, J.W.; Roberts, J.N.; MacNevin, G.; Chaytor, J.L.; Marcus, S.L.; Vederas, J.C.; Ro, D.K.
Double oxidation of the cyclic nonaketide dihydromonacolin L to monacolin J by a single cytochrome P450 monooxygenase, LovA
J. Am. Chem. Soc.
133
8078-8081
2011
Aspergillus terreus (Q9Y7C8)
brenda
Nakamura, T.; Komagata, D.; Murakawa, S.; Sakai, K.; Endo, A.
Isolation and biosynthesis of 3 alpha-hydroxy-3,5-dihydromonacolin L
J. Antibiot.
43
1597-1600
1990
Monascus ruber
brenda
Treiber, L.; Reamer, R.; Rooney, C.; Ramjit, H.
Origin of monacolin L from Aspergillus terreus cultures
J. Antibiot.
42
30-36
1989
Aspergillus terreus
brenda
1.14.14.124 dihydromonacolin L hydroxylase
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