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Literature summary for 1.14.13.222 extracted from

  • Katsuyama, Y.; Li, X.W.; Mueller, R.; Nay, B.
    Chemically unprecedented biocatalytic (AuaG) retro-[2,3]-Wittig rearrangement: a new insight into aurachin B biosynthesis (2014), ChemBioChem, 15, 2349-2352.
    View publication on PubMed

Organism

Organism UniProt Comment Textmining
Stigmatella aurantiaca H1ZZA4
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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
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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
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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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