MACROLIDE BIOSYNTHESIS-II ORIGIN OF THE CARBON SKELETON AND OXYGEN ATOMS OF THE ERYTHROMYCINS

Article abstract of DOI:10.1016/S0040-4020(01)88655-5

Feeding of <1-(13)C>propionate to cultures of Streptomyces erythreus gave erythromycin A and B labeled at C-1, 3, 5, 7, 9, 11 and 13, as established by (13)C NMR analysis of the derived 2'-benzoate esters.Incorporation of <2-(13)C>propionate labled C-2, 4, 6, 8, 10, 12, and 20 while feeding of ethyl<2, 3-(13)C2>succinate, an in vivo precursor of <2,2'-(13)C2>methylmalonate, gave rise to seven pairs of enhanced and coupled doublets in the spectra of labeled erythromycin A and B benzoate.Subsequent incorporation of <1-(18)O2, 1-(13)C>propionate and (13)C NMR analysis established the presence of excess (18)O at C-1, 3, 5, 9, 11, and 13 in both erythromycins A and B, as evidenced by the corresponding isotopically shifted (13)C(18)O peaks.These results establish that in the biosynthesis of erythromycin all the O atoms of the initial aglycone, 6-deoxyerythronolide B (3) originate directly from propionate.

Full text of DOI:10.1016/S0040-4020(01)88655-5

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Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.