66 ポリオキシン及び関連物質の生合成

概要

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Biosynthesis of the nucleoside skeleton of the antibiotic polyoxins and the shunt metabolite octosyl acids was studied utilizing [1-^<13>C]glucose, [6-^<13>C]glucose as well as [U-^<14>C]uridine, [3-^<14>C]-pyruvate, and [3-^<14>C]glycerate. The results strongly suggested the following conclusion. Condensation of uridine-5'-aldehyde and phosphoenolpyruvate would yield intermediate octofuranulose uronic acid. Subsequent oxidative elimination of the terminal two carbons followed by transamination would result in the formation of the polyoxin nucleoside. Conversely, reduction at the ketal carbon would yield octosyl acid. Three polyoxin-non-producing mutants were derived. Isolation and analysis of their metabolites supported strongly that the final step of the polyoxin biosynthesis is the formation of peptide bonds among the pre-formed hyper-modified amino acids. The proposed biosynthetic pathway is summerized in Scheme II.
天然有機化合物討論会の論文
1979-09-20