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Literature summary for 1.1.1.394 extracted from

  • Katsuyama, Y.; Harmrolfs, K.; Pistorius, D.; Li, Y. and Muller, R.
    A semipinacol rearrangement directed by an enzymatic system featuring dual-function FAD-dependent monooxygenase (2012), Angew. Chem. Int. Ed. Engl., 51, 9437-9440.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene auaH, recombinant expression of the C-terminally His6-tagged enzyme in Escherichia coli Stigmatella aurantiaca

Natural Substrates/ Products (Substrates)

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

Organism UniProt Comment Textmining
Stigmatella aurantiaca H1ZZB0 gene auaH
-
Stigmatella aurantiaca Sg a15 H1ZZB0 gene auaH
-

Purification (Commentary)

Purification (Comment) Organism
recombinant C-terminally HIs6-tagged enzyme from Escherichia coli by nickel affinity chromatography Stigmatella aurantiaca

Reaction

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 and Products (Substrate)

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

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

Synonyms Comment Organism
AuaH
-
Stigmatella aurantiaca

Cofactor

Cofactor Comment Organism Structure
NAD+
-
Stigmatella aurantiaca

General Information

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