KEGG   ENZYME: 1.14.13.222
Entry
EC 1.14.13.222              Enzyme                                 

Name
aurachin C monooxygenase/isomerase;
auaG (gene name);
aurachin C monooxygenase
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
Sysname
aurachin C:NAD(P)H:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
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]
Reaction(KEGG)
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]
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]
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
EC 1.14.13.222 created 2016
Pathway
ec00998  Biosynthesis of various antibiotics
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K21272  aurachin C monooxygenase/isomerase
Reference
1  [PMID:22907798]
  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
Angew Chem Int Ed Engl 51:9437-40 (2012)
DOI:10.1002/anie.201204138
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.222
IUBMB Enzyme Nomenclature: 1.14.13.222
ExPASy - ENZYME nomenclature database: 1.14.13.222
BRENDA, the Enzyme Database: 1.14.13.222

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