58 ストレプトバリシンの生合成

概要

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The streptovaricins have aroused considerable interest due to their inhibition of RNA dependent DNA polymerase (Reverse Transcriptase) from RNA tumor viruses and their general antibacterial properties, especially against mycobacteria. The biosynthesis of the antibiotics was studied employing carbon magnetic resonance. All of the carbon atom signals of the streptovaricins were assigned by comparison with other streptovaricins, their oxidation products and an atropisomer which is known to be the first example in natural products, with the aids of standard chemical shift data. The cmr spectra of streptovaricin D biosynthesised in the presence of [1-^<13>C]propionate showed the enrichments at C-1, C-5, C-7, C-9, C-11, C-13, C-15 and C-19 signals. Also observed were the incorporation of [CH_3-^<13>C]-methionine into the 25-methyl, the methylenedioxy and the carbomethoxy methyl groups and the labeling of C-4 and C-18 from [2-^<13>C]malonate. The origin of the benzenoid aromatic ring and the quinone carbon (C_7 unit) and the amide nitrogen remains to be determined. From the fermentation product of streptovaricin were isolated a few new metabolites and their structures were determined by chemical degradation and their spectral studies. The biosynthetic relations of these metabolites to the streptovaricins were also discussed.
天然有機化合物討論会の論文
1975-10-01