Cloned (Comment) | Organism |
---|---|
gene auaH, recombinant expression of the C-terminally His6-tagged enzyme in Escherichia coli | Stigmatella aurantiaca |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
3,4-dihydroxy-2-methyl-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD+ | Stigmatella aurantiaca | - |
4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NADH + H+ | i.e aurachin B | ? | |
3,4-dihydroxy-2-methyl-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD+ | Stigmatella aurantiaca Sg a15 | - |
4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NADH + H+ | i.e aurachin B | ? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Stigmatella aurantiaca | H1ZZB0 | gene auaH | - |
Stigmatella aurantiaca Sg a15 | H1ZZB0 | gene auaH | - |
Purification (Comment) | Organism |
---|---|
recombinant C-terminally HIs6-tagged enzyme from Escherichia coli by nickel affinity chromatography | Stigmatella aurantiaca |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
aurachin B + NAD+ + H2O = 4-[(2E,6E)-farnesyl]-4-hydroxy-2-methyl-3-oxo-3,4-dihydroquinoline 1-oxide + NADH + H+ | reaction mechanism, overview | Stigmatella aurantiaca |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
3,4-dihydroxy-2-methyl-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD+ | - |
Stigmatella aurantiaca | 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NADH + H+ | i.e aurachin B | ? | |
3,4-dihydroxy-2-methyl-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD+ | - |
Stigmatella aurantiaca Sg a15 | 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NADH + H+ | i.e aurachin B | ? |
Subunits | Comment | Organism |
---|---|---|
More | the enzyme possesses a Rossman fold, and both the conserved TGxxxGxG motif for NAD(P)H binding and the catalytic centers important for ketoreduction activity (YxxxK motif and the catalytic Ser residue) | Stigmatella aurantiaca |
Synonyms | Comment | Organism |
---|---|---|
AuaH | - |
Stigmatella aurantiaca |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
NAD+ | - |
Stigmatella aurantiaca |
General Information | Comment | Organism |
---|---|---|
metabolism | the enzyme catalyzes the second step in the biosynthetic pathway from aurachin C to aurachin B. Aurachin C is first converted to 3,4-dihydroxy-2-methy-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide by enzyme AuaG, which is then reduced to aurachin B. The pathway involves the migration of the prenyl group from position C3 to C4, probably via a pinacol type rearrangement. The equilibrium state of AuaG and the instability of 3,4-dihydroxy-2-methy-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide suggests the requirement of immediate reduction catalyzed by AuaH to fix the farnesyl group at the position C4 and prevent the degradation of the intermediate | Stigmatella aurantiaca |
additional information | the enzyme possesses a Rossman fold, and both the conserved TGxxxGxG motif for NAD(P)H binding and the catalytic centers important for ketoreduction activity (YxxxK motif and the catalytic Ser residue) | Stigmatella aurantiaca |