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- W2004030940 abstract "Feeding experiments with D-[6, 6-2H2] D-(6R)-(6-2H1]- and D-(6S)-[6-2H1]glucose in the fermentation of Streptomyces ribosidificus, followed by field desorption MS and 2H NMR analyses of the resulting labeled ribostamycin samples, clearly demonstrated that 1) both hydrogens of the C-6 hydroxymethyl group of D-glucose are stereospecifically incorporated into the C-2 position of 2-deoxystreptamine and 2) the pro S hydrogen of the C-6 position of D-glucose is stereospecifically removed during the elaboration of neosamine C in the biosynthesis of ribostamycin. A plausible mechanism of formation of the deoxy-scyllo-inosose, an early precursor to 2-deoxystreptamine, is suggested to be analogous to the dehydroquinate synthesis in the shikimate pathway and the conversion of the C-6 hydroxymethyl group of D-glucose into the aminomethyl group of neosamine C is likely to involve a dehydrogenation step to a formyl group." @default.
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- W2004030940 date "1989-01-01" @default.
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- W2004030940 title "Mechanism and stereochemistry of the biosynthesis of 2-deoxystreptamine and neosamine C." @default.
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- W2004030940 doi "https://doi.org/10.7164/antibiotics.42.926" @default.
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