103 Neoantimycinの生合成-立体化学的側面(ポスター発表の部)

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The biosynthesis of 2,2-dimethy1-3,4-dihydroxy-5-phenylvaleric acid portion of neoantimycin (1), a metabolite of Streptoverticillium orinoci was examined. During the course of the assignments of ^1H- and ^<13>C-NMR signals of 1, the absolute stereochemistry at C-15 and C-16 were assigned as S and S. Feeding experiments of [^<13>C-Me]- methionine, [3-^<13>C]-sodium propionate and [2-^<13>C]-sodium acetate revealed that the C-10-C-13 portion was biosynthesized from propionate and methyl group of methionine and that methyl group of methionine and C-3 carbon of propionate were incorporated stereospecifically into C-12 and C-13, respectively. The chirality of the methyl group of methionine was found to be inversed when incorporated into C-12 as the results of the feeding experiment of [S-^1H, ^2H, ^3H-Me]-methionine followed by Kuhn-Roth oxidation and chiral analysis of resulting acetate. The intervention of phenylpyruvate was also demonstrated by feeding experiment of L-[U-^<14>C,2,3-H_2]-phenylalanine. The structure of a minor metabolite was elucidated as 2 based on its ^1H-COSY, ^1H-^<13>C-COSY and ^1H-^<13>C long range COSY spectra.
天然有機化合物討論会の論文
1992-09-10