Organism | UniProt | Comment | Textmining |
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Stigmatella aurantiaca | H1ZZA4 | - |
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Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
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2 2,3-dimethyl-4(1H)-quinolinone + NAD(P)H + H+ + O2 | methyl variant of aurachin D | Stigmatella aurantiaca | 3-hydroxy-2-[(3-hydroxy-3-methyl-4-oxo-1,2,3,4-tetrahydroquinolin-2-yl)methyl]-3-methylquinolin-4(3H)-one + NAD(P)+ + H2O | product is formed by dimerization | ? | |
2-methyl-3-geranyl-4(1H)-quinolinone + NAD(P)H + H+ + O2 | geranyl variant of aurachin D | Stigmatella aurantiaca | 3-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-2-methyl-2,3-dihydroquinolin-4(1H)-one + NAD(P)+ + H2O | - |
? | |
2-methyl-3-isoprenyl-4(1H)-quinolinone + NAD(P)H + H+ + O2 | isoprenyl variant of aurachin D | Stigmatella aurantiaca | 2-methyl-3-[(2-methylbut-3-en-2-yl)oxy]-2,3-dihydroquinolin-4(1H)-one + NAD(P)+ + H2O | during the AuaG-catalysed transformation, the transient C2-C3 epoxide can be formed and opened to the tertiary alcoholate. The ether product is supposed to arise from rapid retro-[2,3]-Wittig rearrangement assisted by the presence of both carbonyl and iminium functions | ? | |
aurachin C + NAD(P)H + H+ + O2 | - |
Stigmatella aurantiaca | 4-hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide + NAD(P)+ + H2O | AuaG performs epoxidation of the C2-C3 bond of aurachin C. The resulting epoxide is opened, thereby resulting in the imine N-oxide and the alpha-keto tertiary alcoholate | ? | |
additional information | AuaG is able to oxidize short-chain analogues of aurachin D. A retro-[2,3]-Wittig rearrangement is observed with isoprenyl substrate analogues. Saturated-chain analogues of N-oxidized aurachin C are not transformed by the C3 to C4 semipinacol reaction | Stigmatella aurantiaca | ? | - |
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