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- W1977027860 abstract "Nogalamycin is an anthracycline polyketide antibiotic that contains two deoxysugars, at positions C-1 and C-7. Previous biosynthetic studies conducted in vivo affiliated snoaL2 with an unusual C-1 hydroxylation reaction, but in vitro activity was not established. Here, we demonstrate that inactivation of either snoaL2 or snoaW resulted in accumulation of two nonhydroxylated metabolites, nogalamycinone and a novel anthracycline 3′,4′-demethoxy-nogalose-nogalamycinone. The C-1 hydroxylation activity was successfully reconstructed in vitro in the presence of the two enzymes, NAD(P)H and the substrates. Based on relative reaction efficiencies, 3′,4′-demethoxy-nogalose-nogalamycinone was identified as the likely natural substrate. A biosynthetic model was established where the atypical short-chain alcohol dehydrogenase SnoaW reduces the anthraquinone to a dihydroquinone using NADPH, which enables activation of oxygen and formation of a hydroperoxy intermediate. Finally, protonation of the intermediate by SnoaL2 yields the 1-hydroxylated product." @default.
- W1977027860 created "2016-06-24" @default.
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- W1977027860 date "2012-05-01" @default.
- W1977027860 modified "2023-10-03" @default.
- W1977027860 title "Discovery of a Two-Component Monooxygenase SnoaW/SnoaL2 Involved in Nogalamycin Biosynthesis" @default.
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- W1977027860 doi "https://doi.org/10.1016/j.chembiol.2012.04.009" @default.
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