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EC 1.14.13.222 Details
show Brenda entryEC number
1.14.13.222
Accepted name
aurachin C monooxygenase/isomerase
Reaction
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);;(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;;(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
Other name(s)
auaG (gene name),
aurachin C monooxygenase
Systematic name
aurachin C:NAD(P)H:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
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.
History
created 2016
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1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.6.99.4 created 1965, deleted 1972 1.6.99.8 created 1972, deleted 2002 1.6.99.9 created 1972, deleted 2002 1.6.99.10 created 1978, deleted 1981 1.6.99.11 created 1989, deleted 2002 1.6.99.12 created 1989, deleted 2002 1.6.99.13 created 1992, deleted 2002 1.14.13.45 created 1992, deleted 2003
