Skip to main content
SpringerLink
Log in

Antibacterial glycopeptide antibiotics (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The structures of the most important antibacterial glycopeptide antibiotics and the mechanisms of their activity and resistance to them are examined. Researches on the total synthesis of antibiotics and model compounds are discussed. The chemical modification of antibiotics (changing the amino acid composition) and also the modification of fragments of the molecule that do not take part in interaction with the target but make it possible to overcome the resistance of bacteria to antibiotics of this group are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. N. V. Beloborodova, Rus. Med. Zh.,6, 832 (1998).

    Google Scholar 

  2. T. I. Nicas, M. L. Zeckel, and D. K. Braun, Trends Miocrobiol.,5, 240 (1997).

    CAS  Google Scholar 

  3. F. Parenti and B. Cavalleri, J. Antibiot.,42, 1882 (1989).

    CAS  Google Scholar 

  4. J. C. J. Barna and D. H. Williams, Ann. Rev. Microbiol.,38, 339 (1984).

    CAS  Google Scholar 

  5. N. Woodford, A. P. Johnson, D. Morrison, and D. C. E. Speller, Clin. Microbiol. Rev.,8, 585 (1995).

    CAS  Google Scholar 

  6. T. D. H. Bugg, G. D. Wright, S. Dutka-Mallen, M. Arthur, P. Courvalin, and C. T. Walsh, Biochemistry,30, 1048 (1991).

    Google Scholar 

  7. U. Gerhard, J. P. Mackay, R. A. Maplestone, and D. H. Williams, J. Am. Chem. Soc.,115, 232 (1993).

    Article  CAS  Google Scholar 

  8. E. N. Olsuf'eva (Olsufyeva), T. J. D. Jorgensen, O. A. Mirgorodskaya, A. Y. Pavlov, O. V. Miroshnikova, and M. N. Preobrazhenskaya, ICCA-1, Bologna, Italy, August 30 to September 4, 1998, PC 12.

  9. J. P. Mackay, U. Gerhard, D. A. Beauregard, M. S. Wastwell, M. S. Searle, and D. H. Williams, J. Am. Chem. Soc.,116, 4581 (1994).

    CAS  Google Scholar 

  10. D. T. W. Chu, J. J. Plattner, and L. Katz, J. Med. Chem.,39, 3853 (1996).

    Article  CAS  Google Scholar 

  11. A. S. Trenin and E. N. Olsuf'eva, Bioorgan. Khim.,23, 851 (1997).

    CAS  Google Scholar 

  12. R. Beugelmans, A. Bigot, and J. Zhu, Tetrahedron Lett.,35, 5649 (1994).

    CAS  Google Scholar 

  13. A. V. Rama Rao, M. K. Gurjar, K. L. Reddy, and A. S. Rao, Chem. Rev.,95, 2135 (1995).

    Google Scholar 

  14. J. Zhu,Synlett., 133 (1997).

  15. C. Vergne, M. Bois-Choussy, R. Beugelmans, and J. Zhu, Tetrahedron Lett.,38, 1403 (1997).

    Article  CAS  Google Scholar 

  16. J. Zhu, T. Laib, J. Chastanet, and R. Beugelmans, Angew. Chem. Int. Ed. Engl.,35, 2517 (1996).

    CAS  Google Scholar 

  17. D. L. Bogerd, R. M. Borzilleri, and S. Nukui, Bioorg. Med. Chem. Lett.,5, 3091 (1995).

    Google Scholar 

  18. A. V. Rama Rao, K. L. Reddy, A. S. Rao, T. V. S. K. Vittal, M. M. Reddy, and P. L. Pathy, Tetrahedron Lett.,37, 3023 (1996).

    Article  Google Scholar 

  19. D. A. Evans and P. S. Watson, Tetrahedron Lett.,37, 3251 (1996).

    CAS  Google Scholar 

  20. D. L. Boger, Y. Nomoto, and B. R. Teegarden, J. Org. Chem.,58, 1425 (1993).

    CAS  Google Scholar 

  21. Y. Suzuki, S. Nishiyama, and S. Yamamura, Tetrahedron Lett.,30, 6043 (1989).

    CAS  Google Scholar 

  22. D. A. Evans, J. A. Elleman, and K. M. DeVries, J. Am. Chem. Soc.,111, 8912 (1989).

    CAS  Google Scholar 

  23. D. A. Evans, C. J. Dinsmore, D. A. Evrard, and K. M. DeVries, J. Am. Chem. Soc.,115, 6426 (1993).

    CAS  Google Scholar 

  24. K. C. Nicolaou, J. M. Ramanjulu, S. Natarajan, S. Brase, H. Li, C. N. C. Boddy, and F. Rubsam, J. Am. Chem. Soc.,119, 3421 (1997).

    CAS  Google Scholar 

  25. N. Pant and A. D. Hamilton, J. Am. Chem. Soc.,110, 2002 (1988).

    Article  CAS  Google Scholar 

  26. S. Nishiyama, K. Nakamura, Y. Suzuki, and S. Yamamura, Tetrahedron Lett.,27, 4481 (1986).

    CAS  Google Scholar 

  27. A. J. Pearson, P. Zhang, and G. Bignan, J. Org. Chem.,62, 4536 (1997).

    CAS  Google Scholar 

  28. S. Nishiyama, Y. Suzuki, and S. Yamamura, Tetrahedron Lett.,30, 379 (1989).

    CAS  Google Scholar 

  29. K. Nakamura, S. Nishiyama, and S. Yamamura, Tetrahedron Lett.,36, 8621 (1995).

    CAS  Google Scholar 

  30. R. Beugelmans, M. Bois-Choussy, C. Vergne, J. P. Bouillon, and J. Zhu, J. Chem. Soc. Chem. Commun., 1029 (1996).

  31. D. A. Evans and C. J. Dinsmore, Tetrahedron Lett.,34, 6029 (1993).

    CAS  Google Scholar 

  32. K. C. Nicolaou, X. J. Chu, J. M. Ramanjulu, S. Natarajan, S. Brase, F. Rubsam, and C. N. C. Boddy, Angew. Chem.,109, 1518 (1997).

    Google Scholar 

  33. A. G. Brown, M. J. Crimmin, and P. D. Edwards, J. Chem. Soc. Perkin Trans. I, 123 (1992).

    Google Scholar 

  34. D. A. Evans, C. J. Dinsmore, A. M. Ratz, D. A. Evrard, and J. C. Barrow, J. Am. Chem. Soc.,119, 3417 (1997).

    CAS  Google Scholar 

  35. R. Beugelmans, S. Bourdet, and J. Zhu, Tetrahedron Lett.,36, 1279 (1995).

    CAS  Google Scholar 

  36. R. Beugelmans, L. Neuville, M. Bois-Choussy, and J. Zhu, Tetrahedron Lett.,36, 8787 (1995).

    CAS  Google Scholar 

  37. M. Bois-Choussy, C. Vergne, L. Neuville, R. Beugelmans, and J. Zhu, Tetrahedron Lett.,38, 5795 (1997).

    Article  CAS  Google Scholar 

  38. D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorrow, J. Am. Chem. Soc.,112, 4011 (1990).

    CAS  Google Scholar 

  39. D. A. Evans, D. A. Evrard, S. D. Rychnovsky, T. Froh, W. G. Whittingham, and K. M. DeVries, Tetrahedron Lett.,33, 1189 (1992).

    Article  CAS  Google Scholar 

  40. D. A. Evans and A. E. Weber, J. Am. Chem. Soc.,109, 7151 (1987).

    CAS  Google Scholar 

  41. D. A. Evans, C. J. Dinsmore, and C. J. Ratz, Tetrahedron Lett.,38, 3189 (1997).

    CAS  Google Scholar 

  42. D. A. Evans, J. C. Barrow, P. S. Watson, A. M. Ratz, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. A. Ellman, S. D. Rychnovsky, and J. Lacour, J. Am. Chem. Soc.,119, 3419 (1997).

    CAS  Google Scholar 

  43. J. L. Radkiewicz, H. Zipse, S. Clarke and K. N. Houk, J. Am. Chem. Soc.,118, 9148 (1996).

    Article  CAS  Google Scholar 

  44. L. A. Carpino and A. El-Faham, J. Org. Chem.,60, 3561 (1995).

    CAS  Google Scholar 

  45. A. M. Wageningen, P. N. Kirkpatrick, D. H. Williams, B. R. Harris, J. Kershaw, N. J. Lennard, M. Jones, S. J. M. Jones, and P. J. Solenberg, Chem. Biol.,5, 155 (1998).

    Google Scholar 

  46. P. J. Solenberg, P. Matsushima, D. R. Stack, S. C. Wilkie, R. C. Tompson, and R. H. Baltz, Chem. Biol.,4, 195 (1997).

    Article  CAS  Google Scholar 

  47. M. F. Cristofaro, D. A. Beauregard, H. Yan, N. J. Osborn, and D. H. Williams, J. Antibiot.,48, 805 (1995).

    CAS  Google Scholar 

  48. O. V. Miroshnikov, T. F. Berdnikov, E. N. Olsuf'eva, A. Y. Pavlov, M. I. Reznikova, M. N. Preobrazhenskaya, R. Ciabatti, A. Malabarba, and L. Colombo, J. Antibiot.,49, 1157 (1996).

    Google Scholar 

  49. A. Malabarba and R. Ciabatti, J. Med. Chem.,37, 2988 (1994).

    Article  CAS  Google Scholar 

  50. A. Malabarba, R. Ciabatti, J. Kettenring, P. Ferrari, K. Vekey, E. Bellasio, and M. Denaro, J. Org. Chem.,61, 2137 (1996).

    CAS  Google Scholar 

  51. A. Malabarba, R. Ciabatti, E. Gerli, F. Ripamonti, P. Ferrari, L. Colombo, and M. Denaro, J. Org. Chem.,61, 2151 (1996).

    CAS  Google Scholar 

  52. A. Malabarba, R. Ciabatti, E. Gerli, F. Ripamonti, P. Ferrari, L. Colombo, E. N. Olsuf'eva, A. Y. Pavlov, M. I. Reznikova, E. I. Lazhko, and M. N. Preobrazhenskaya, J. Antibiot.,49, 70 (1996).

    Google Scholar 

  53. A. Yu. Pavlov, E. N. Olsuf'eva, O. V. Miroshnikova, M. I. Reznikova, É. I. Lazhko, A. Malabarba, R. Ciabatti (Chabatti), and M. N. Preobrazhenskaya, Bioorgan. Khim.,23, 410 (1997).

    CAS  Google Scholar 

  54. G. S. Katrukha and A. B. Silaev, Chem. Pept. Proteins,3, 289 (1986).

    CAS  Google Scholar 

  55. A. Malabarba and F. Parenti, Curr. Antimicrob. Patents,2, 263 (1990).

    Google Scholar 

  56. R. D. G. Cooper and R. C. Thompson, Ann. Rep. Med. Chem., Chap. 14, 131 (1996).

    Google Scholar 

  57. A. Malabarba, T. I. Nicas, and R. C. Thompson, Med. Res. Rev.,17, 69 (1997).

    Article  CAS  Google Scholar 

  58. A. Malabarba, T. I. Nicas, and R. Ciabatti, Eur. J. Med. Chem.,32, 459 (1997).

    Article  CAS  Google Scholar 

  59. A. Yu. Pavlov and M. N. Preobrazhenskaya, Bioorgan. Khim.,24, 644 (1998).

    CAS  Google Scholar 

  60. R. Nagarajan, A. A. Schabel, J. L. Occolowitz, F. T. Counter, J. L. Ott, and A. M. Felty-Duckworth, J. Antibiot.,42, 63 (1989).

    CAS  Google Scholar 

  61. E. N. Olsuf'eva, T. F. Berdnikova, N. Yu. Dokshina, N. N. Lomakina, G. I. Orlova, I. V. Malkova, and I. N. Prozorova, Antibiotiki i Khimioterapiya,34, 352 (1989).

    Google Scholar 

  62. A. Yu. Pavlov, T. F. Berdnikova, E. N. Olsuf'eva, G. I. Orlova, and M. N. Preobrazhenskaya, Khim-farm. Zh.,29, 46 (1995).

    CAS  Google Scholar 

  63. T. I. Nicas, C. T. Cole, D. A. Preston, A. A. Schabel, and R. Nagarajan, Antimicrob Agents Chemother.,33, 1477 (1989).

    CAS  Google Scholar 

  64. R. Nagarajan, D. M. Berry, and A. A. Schabel, Eur. Pat. Appl. 0.435.503 (1991).

  65. R. D. G. Cooper, N. J. Snyder, M. J. Zweifel, M. A. Staszak, S. C. Wilkie, T. I. Nicas, D. L. Mullen, T. F. Butler, M. J. Rodrigues, B. E. Huff, and R. C. Thompson, J. Antibiot.,49, 575 (1996).

    CAS  Google Scholar 

  66. M. J. Rodriguez, N. J. Snyder, M. J. Zweifel, S. C. Wilkie, D. R. Stack, R. D. G. Cooper, T. I. Nicas, D. L. Mullen, T. F. Butler, and R. C. Thompson, J. Antibiot.,51, 560 (1998).

    CAS  Google Scholar 

  67. T. I. Nicas, D. L. Mullen, J. E. Flokowitsch, D. A. Preston, N. J. Snyder, M. J. Zweifel, S. C. Wilkie, M. J. Rodriguez, R. C. Thompson, and R. D. G. Cooper, Antimicrob. Agents Chemother.,40, 2194 (1996).

    CAS  Google Scholar 

  68. A. Y. Pavlov, M. N. Preobrazhenskaya, A. Malabarba, and R. Ciabatti, J. Antibiot.,51, 525 (1998).

    CAS  Google Scholar 

  69. A. Malabarba, A. Trani, P. Ferrari, R. Pallanza, and B. Cavalleri, J. Antibiot.,40, 1572 (1987).

    CAS  Google Scholar 

  70. A. Y. Pavlov, E. N. Olsuf'eva, T. F. Berdnikova, I. V. Malkova, M. N. Preobrazhenskaya and G. D. Risbridger, J. Antibiot.,47, 225 (1994).

    CAS  Google Scholar 

  71. A. Yu. Pavlov, E. N. Olsuf'eva, T. F. Berdnikova, B. V. Rozynov, L. G. Aleksandrova, I. V. Malkova, and M. N. Preobrazhenskaya Bioorgan. Khim.,17, 849 (1991).

    CAS  Google Scholar 

  72. A. Trani, A. Malabarba, P. Ferrari, R. Pallanza, M. Berti, and R. Ciabatti,43, 1471 (1990).

  73. A. Malabarba, P. Ferrari, G. Cietto, R. Pallanza, and M. Berti, J. Antibiot.,42, 1800 (1989).

    CAS  Google Scholar 

  74. A. Y. Pavlov, T. F. Berdnikova, E. N. Olsuf'eva, O. V. Miroshnikova, S. T. Filipposyants, and M. N. Preobrazhenskaya, J. Antibiot.,49, 194 (1996).

    CAS  Google Scholar 

  75. A. Malabarba, A. Trani, P. Stazzolini, G. Cietto, P. Ferrari, G. Tarzia, R. Pallanza, and M. Berti, J. Med. Chem.,32, 2450 (1989).

    CAS  Google Scholar 

  76. A. Malabarba, R. Ciabatti, J. Kettenring, R. Scotti, G. Candiani, R. Pallanza, M. Berti, and B. P. Goldstein, J. Med. Chem.,35, 4054 (1992).

    Article  CAS  Google Scholar 

  77. A. Malabarba, R. Ciabatti, R. Scotti, B. P. Goldstein, P. Ferrari, M. Kurz, B. P. Andreini, and M. Denaro, J. Antibiot.,48, 869 (1995).

    CAS  Google Scholar 

  78. M. T. Kenny, M. A. Brackman, and J. K. Dulworth, Antimicrob. Agents Chemother.,39, 1589 (1995).

    CAS  Google Scholar 

  79. N. J. Snyder, M. J. Zweifel, R. D. G. Cooper, M. J. Rodriguez, T. I. Nicas, D. L. Mullen, and T. F. Butler, 37th ICAAC, Toronto, Canada (1997), F-2.

  80. A. Y. Pavlov, E. I. Lazhko, and M. N. Preobrazhenskaya, J. Antibiot.,50, 509 (1997).

    CAS  Google Scholar 

  81. A. Y. Pavlov, M. N. Preobrazhenskaya, A. Malabarba, R. Ciabatti, and L. Colombo, J. Antibiot.,51, 73 (1998).

    CAS  Google Scholar 

  82. N. E. Allen, D. L. LeTourneau, and J. N. Hobbs, J. Antibiot.,50, 677 (1997).

    CAS  Google Scholar 

Download references

Authors
  1. M. N. Preobrazhenskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. V. Miroshnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Yu. Pavlov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. N. Olsuf'eva
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of Research into New Antibiotics, RAMN, Moscow, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1605–1631, December, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Preobrazhenskaya, M.N., Miroshnikova, O.V., Pavlov, A.Y. et al. Antibacterial glycopeptide antibiotics (review). Chem Heterocycl Compd 34, 1359–1381 (1998). https://doi.org/10.1007/BF02317806

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02317806

Keywords

Search

Navigation