The biosynthesis of scytalone, a simple derivative of tetralone, has been studied by using [1, 2-13C2] and [2-13C, 2-2H3]-acetate. Scytalone labelled by [1, 2-13C2]-acetate showed an unusual coupling pattern in the 13C-nuclear magnetic resonance (NMR) spectrum, indicating that all the carbon atoms coupled to both of the adjacent carbons. The results clearly demonstrate that scytalone is biosynthesized via a symmetrical aromatic intermediate, 1, 3, 6, 8-tetrahydroxynaphthalene. Incorporation of 2H into C-4 and -5 from [2-13C, 2-2H3]-acetate was demonstrated by 1H and 2H decoupled 13C-NMR. In contrast, 2H was not observed on the other potential sites of labelling, C-2 and C-7. It has been shown that the use of [2-13C, 2-2H3]-acetate is effective in tracing the fate of acetate hydrogen in polyketide biosynthesis.
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Sankawa et al. (1981) studied this question.