Entry |
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Name |
aurachin C monooxygenase/isomerase;
auaG (gene name);
aurachin C monooxygenase
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Class |
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
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Sysname |
aurachin C:NAD(P)H:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
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Reaction(IUBMB) |
aurachin C + NAD(P)H + H+ + O2 = 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD(P)+ + H2O (overall reaction) [RN: R11382 R11383];
(1a) aurachin C + NAD(P)H + H+ + O2 = 2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one + NAD(P)+ + H2O [RN: R11384 R11385];
(1b) 2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one = 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide [RN: R11386]
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Reaction(KEGG) |
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Substrate |
aurachin C [CPD: C21330];
NADH [CPD: C00004];
NADPH [CPD: C00005];
H+ [CPD: C00080];
O2 [CPD: C00007];
2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one [CPD: C21331]
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Product |
4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide [CPD: C21141];
NAD+ [CPD: C00003];
NADP+ [CPD: C00006];
H2O [CPD: C00001];
2-hydroxy-1a-methyl-7a-[(2E,6E)-farnesyl]-1a,2-dihydrooxireno[2,3-b]quinolin-7(7aH)-one [CPD: C21331]
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Comment |
The aurachin C monooxygenase from the bacterium Stigmatella aurantiaca accepts both NADH and NADPH as cofactor, but has a preference for NADH. It catalyses the initial steps in the conversion of aurachin C to aurachin B. The FAD-dependent monooxygenase catalyses the epoxidation of the C2-C3 double bond of aurachin C, which is followed by a semipinacol rearrangement, causing migration of the farnesyl group from C3 to C4.
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History |
EC 1.14.13.222 created 2016
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Pathway |
ec00998 | Biosynthesis of various secondary metabolites - part 2 |
ec01110 | Biosynthesis of secondary metabolites |
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Orthology |
K21272 | aurachin C monooxygenase/isomerase |
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Reference |
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Authors |
Katsuyama Y, Harmrolfs K, Pistorius D, Li Y, Muller R |
Title |
A semipinacol rearrangement directed by an enzymatic system featuring dual-function FAD-dependent monooxygenase. |
Journal |
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Sequence |
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Other DBs |
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