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Further studies on the biosynthesis of the avermectins

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Journal of Industrial Microbiology

Summary

The biosynthesis of avermectins was studied further inStreptomyces avermitilis MA5502 by feeding experiments with labeled precursors.13C-NMR analysis of the compounds biosynthesized from [2-13C]acetate, [1,2-13C2]acetate, [3-13C]propionate and [2,3-13C2]propionate confirmed that the aglycone of avermectins is made from seven intact acetate and five propionate units. Feeding experiments with [1-13C]2-methylbutyrate and [1-13C]isobutyrate have shown that 2-methylbutyrate and isobutyrate are immediate precursors of the starter units of the polyketide chains of avermectin ‘a’ and ‘b’ components, respectively. The3H/14C doublelabeling experiments suggest that the two oleandrose moieties are derived from glucose.

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References

  1. Albers-Schonberg, G., B.H. Arison, J.C. Chabala, A.W. Douglas, P. Eskola, M.H. Fisher, A. Lusi, H. Mrozik, J.L. Smith and R.L. Tolman. 1981. Avermectins. Structure Determination. J. Am. Chem. Soc. 103: 4216–4221.

    Google Scholar 

  2. Albers-Schonberg, G., R.T. Goegelman, L. Kaplan, A. Kempf and J.B. Tunac. unpublished results.

  3. Burg, R.W., B.M. Miller, E.E. Baker, J. Birnbaum, S.A. Curri, R. Hartman, Y.-L. Kong, R.L. Monaghan, G. Olson, I. Putter, J.-B. Tunac, H. Wallick, E.O. Stapley, R. Oiwa and S. Omura. 1979. Avermectins, new family of potent anthelmintic agents: Producing organism and fermentation. Antimicrob. Agents Chemother. 15: 361–367.

    PubMed  Google Scholar 

  4. Cane, D.E., T.-C. Ziang, L. Kaplan, M.K. Nallin; M.D. Schulman, O.D. Hensens, A.W. Douglas and G. Albers-Schonberg. 1983. The biosynthetic origin of the carbon skeleton and oxygen atoms of the avermectins. J. Am. Chem. Soc. 105: 4110–4112.

    Google Scholar 

  5. Kass, I.S., C.C. Wang, J.P. Walrond and A.O.W. Stretton. 1980. Avermectin Bla, a new paralyzing anthelmintic that affects interneurons and inhibitory motor-neurons in Ascaris. Proc. Natl. Acad. Sci. U.S.A. 77: 6211–6215.

    PubMed  Google Scholar 

  6. Pong, S.S., R. Dehaven and C.C. Wang. 1982. A comparative study of avermectin Bla and other modulators of the α-aminobutyric acid receptor chloride ion channel complex. J. Neuroscience 2: 966–971.

    Google Scholar 

  7. Putter, I., J.G. MacConnell, F.A. Preiser, S.S. Ristich and R.A. Dybas. 1981. Avermectins: novel insecticides, acaricides and nematicides from a soil microorganism. Experientia 37: 963–966.

    Google Scholar 

  8. Springer, J.L., B.H. Arison, J.M. Hirschfield and K. Hoogsteen. 1981. The absolute stereochemistry and conformation of avermectin B2a aglycone and avermectin Bla. J. Am. Chem. Soc. 103: 4221–4224.

    Google Scholar 

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Chen, T.S., Arison, B.H., Gullo, V.P. et al. Further studies on the biosynthesis of the avermectins. Journal of Industrial Microbiology 4, 231–237 (1989). https://doi.org/10.1007/BF01574080

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  • DOI: https://doi.org/10.1007/BF01574080

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