Synthesis of extended bacterial cell-wall precursor analogues for ligand binding studies with glycopeptide antibiotics

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Thomas Staroske, Jochen Görlitzer, Richard M. H. Entress, Matthew A. Cooper and Dudley H. Williams


Abstract

The synthesis of bacterial cell-wall precursor analogues, which resemble the naturally occurring precursor (lipid II) more closely than those hitherto used in NMR binding studies with glycopeptide antibiotics, is reported.


References

  1. H. J. Rogers, H. R. Perkins and J. B. Ward, Microbial cell walls and membranes, Chapman and Hall, London, 1980 Search PubMed.
  2. H. R. Perkins, Biochem. J., 1969, 111, 195 CAS.
  3. D. H. Williams, Acc. Chem. Res., 1984, 17, 364 CrossRef CAS.
  4. J. E. Geraci and P. E. Hermans, Mayo Clin. Proc., 1983, 58, 88 Search PubMed.
  5. M. Foldes, R. Munro, T. C. Sorrell, S. Shankar and M. Toohey, J. Antimicrob. Chemother., 1983, 11, 21 CAS.
  6. H. C. Neu, Science, 1992, 257, 1064 CrossRef CAS.
  7. C. T. Walsh, S. L. Fisher, I.-S. Park, M. Prahalad and Z. Wu, Chem. Biol., 1996, 3, 21 CrossRef CAS.
  8. R. J. Dancer, A. C. Try, G. J. Sharman and D. H. Williams, Chem. Commun., 1996, 1445 RSC.
  9. N. E. Allen, D. L. LeTourneau and J. N. Hobbs, J. Antibiot., 1997, 50, 677 CAS.
  10. D. A. Beauregard, D. H. Williams, M. N. Gwynn and D. J. C. Knowles, Antimicrob. Agents Chemother., 1995, 39, 781 CAS.
  11. J. P. Mackay, U. Gerhard, D. A. Beauregard, M. S. Westwell, M. S. Searle and D. H. Williams, J. Am. Chem. Soc., 1994, 116, 4581 CrossRef CAS.
  12. G. J. Sharman, A. C. Try, R. J. Dancer, Y. R. Cho, T. Staroske, B. Bardsley, A. J. Maguire, M. A. Cooper, D. P. O'Brien and D. H. Williams, J. Am. Chem. Soc., 1997, 119, 12041 CrossRef CAS.
  13. A. C. Try, G. J. Sharman, R. J. Dancer, B. Bardsley, R. M. H. Entress and D. H. Williams, J. Chem. Soc., Perkin Trans. 1, 1997, 2911 RSC.
  14. D. H. Williams, Nat. Prod. Rep., 1996, 13, 469 RSC.
  15. S. A. Hitchcock, C. N. Eid, J. A. Aikins, M. Zia-Ebrahimi and L. C. Blaszczak, J. Am. Chem. Soc., 1998, 120, 1916 CrossRef CAS.
  16. R. T. Lee and Y. C. Lee, Carbohydr. Res., 1974, 37, 193 CrossRef CAS.
  17. Y. Matsushima and J. T. Park, J. Org. Chem., 1962, 27, 3581.
  18. S. Kobayashi, T. Fukuda, H. Yukimasa, M. Fujino, I. Azuma and Y. Yamamura, Bull. Chem. Soc. Jpn., 1980, 53, 2570 CAS.
  19. R. Kuhn, H. H. Baer and A. Seeliger, Liebigs Ann. Chem., 1958, 611, 236 Search PubMed.
  20. P. J. Garegg, H. Hultberg and S. Wallin, Carbohydr. Res., 1982, 108, 97 CrossRef.
  21. S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371 RSC.
  22. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34, 2039 CrossRef CAS.
  23. G. Brooks, P. D. Edwards, J. D. I. Hatto, T. C. Smale and R. Southgate, Tetrahedron, 1995, 51, 7999 CrossRef CAS.
  24. H. W. Fehlhaber, M. Girg, G. Seibert, K. Hobert, P. Welzel, Y. van Heijenoort and J. van Heijenoort, Tetrahedron, 1990, 46, 1557 CrossRef CAS.
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