57 ^<13>C-NMRによる16員環macrolide抗生物質の生合成研究

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According to previous reports, the aglycone carbons of the 16-membered macrolide antibiotic, magnamycin A, 1 are derived from nine acetates, one propionate and one methionine as shown in Fig. 1. As an application of a recent systematic ^<13>C-NMR study of 16-membered macrolide antibiotic, the validity of these investigation was reexamined on leucomycin A_3 2 which is structurally similar to magnamycin A. It was found that carbons-5, -6, -17 and -18 of leucomycin A_3, 2 were derived from butyrate and carbons-3 and -4 on the aglycone arose from outside of acetate contrary to the proposal in the study on magnamycin biosynthesis. Although the origin of the carbons-3 and -4 is not yet known at present time, this finding let us to investigate the origin for the carbons-3 and -4 of the aglycone of tylosin which has different carbon skeleton from leucomycin or magnamycin (Fig. 3). Consequently, the metabolic origin, acetate, propionate and butyrate was proposed as shown in Fig. 5. The addition of [1-^<13>C]butyrate to a fermentation medium of tylosin showed the enrichment for carbons-3, -7, -11, -13 and -15 of aglycone as like as carbon-5 which is predicted to be enriched by the precursor. On the other hand, carbons-4, -8, -12, -14 and -16 were enriched as like as carbon-19 by [4-^<13>C]2-ethylmalonate. The metabolic pathway is not yet clear, however these precursors are thought to be partially incorporated to the aglycone of tylosin via propionate.
天然有機化合物討論会の論文
1975-10-01

57 ^<13>C-NMRによる16員環macrolide抗生物質の生合成研究

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