Skip to main content

Accessing carbohydrate-based combinatorial libraries through solid phase and solution phase approaches

  • Chapter

Part of the book series: Annual Reports in Combinatorial Chemistry and Molecular Diversity ((ARCC,volume 2))

Abstract

The pursuit of chemical diversity for the purpose of drug discovery has focused primarily on the generation of peptide and heterocyclic small molecule combinatorial libraries [1–3]. With genomics initiatives beginning to dramatically increase the number of interesting biomolecular targets, a great need has arisen for expanding the universe of molecular structures available for screening. Although carbohydrates play fundamental roles in many biological processes [4,5] and are found as structural units in many drugs [6,7], they are poorly represented in the historical structurally biased chemical sample collections being used by most drug discovery organizations in their screening programs. However, it is because of their biological importance and unique chemical characteristics that carbohydrates are valuable in generating leads through drug discovery screening efforts.

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

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Gordon, E. M., Barrett, R. W., Dower, W. J., Fodor, S. P. A. and Gallop, M. A., J. Med. Chem., 37 (1994) 1385.

    Google Scholar 

  2. Gallop, M. A., Barrett, R. W., Dower, W. J., Fodor, S. P. A. and Gordon, E. M., J. Med. Chem., 37 (1994) 1233.

    Google Scholar 

  3. Nefzi, A., Ostresh, J. M. and Houghten, R. A., Chem. Rev., 97 (1997) 449.

    Article  CAS  Google Scholar 

  4. Varki, A., Glycobiology, 3 (1993) 97.

    Article  CAS  Google Scholar 

  5. Rademacher, T. W., Parekh, R. B. and Dwek, R. A., Annu. Rev. Biochem., 57 (1988) 785.

    Article  CAS  Google Scholar 

  6. Petitou, M., In Kovac, P. (Ed.), Synthetic Oligosaccharides: Indispensable Probes for the Life Sciences, ACS Symposium Series 560, American Chemical Society, Washington, DC, 1994, p. 19.

    Book  Google Scholar 

  7. Musser, J. H., Anderson, M. B. and Fugedi, P., Pharmaceutical News, 3 (1996) 11.

    CAS  Google Scholar 

  8. Yan, L., Taylor, C. M., Goodnow Jr., R. and Kahne, D., J. Am. Chem. Soc., 116 (1994) 6953.

    Article  CAS  Google Scholar 

  9. Danishefsky, Si.,. McClure, K. F., Randolph, J. T. and Ruggeri, R. B., Science, 260 (1993) 1307.

    Google Scholar 

  10. Randolph, J. T., McClure, K. F. and Danishefsky, S. J., J. Am. Chem. Soc., 117 (1995) 5712.

    Article  CAS  Google Scholar 

  11. Hunt, J. A. and Roush, W. R., J. Am. Chem. Soc., 118 (1996) 9998.

    Article  CAS  Google Scholar 

  12. Rademann, J. and Schmidt, R. R., J. Org. Chem., 62 (1997) 3650.

    Article  CAS  Google Scholar 

  13. Nicolaou, K. C., Winssinger, N., Pastor, J. and DeRoose, F., J. Am. Chem. Soc., 119 (1997) 449.

    Article  CAS  Google Scholar 

  14. Ito, Y. and Ogawa, T., J. Am. Chem. Soc., 119 (1997) 5562.

    Article  CAS  Google Scholar 

  15. Rodebaugh, R., Joshi, S., Fraser-Reid, B. and Geysen, H. M., J. Org. Chem., 62 (1997) 5660.

    Article  CAS  Google Scholar 

  16. Frechet, J. M. and Schuerch, C., J. Am. Chem. Soc., 93 (1971) 492.

    Article  Google Scholar 

  17. Frechet, J. M. and Schuerch, C., Carbohydr. Res., 22 (1972) 399.

    Article  CAS  Google Scholar 

  18. Frechet, J. M. and Schuerch, C., J. Am. Chem. Soc., 94 (1972) 604.

    Article  CAS  Google Scholar 

  19. Halcomb, R. L., Huang, H. and Wong, C. -H., J. Am. Chem. Soc., 116 (1994) 11315.

    Article  CAS  Google Scholar 

  20. Wong, C. -H., Halcomb, R. L., Ichikawa, Y. and Kajimoto, T., Angew. Chem., Int. Ed. Engl., 34 (1995) 521.

    Google Scholar 

  21. Schuster, M., Wang, P., Paulson, J. C. and Wong, C. -H., J. Am. Chem. Soc., 116 (1994) 1135.

    Google Scholar 

  22. Liang, R., Yan, L., Loebach, J., Ge, M., Uozumi, Y., Sekanina, K., Horan, N., Gildersleeve, J., Thompson, C., Smith, A., Biswas, K., Still, W. C. and Kahne, D., Science, 274 (1996) 1520.

    Article  CAS  Google Scholar 

  23. Ohlmeyer, M. J., Swanson, R. N., Dillard, L. W., Reader, J. C., Asouline, G., Kobayashi, R., Wigler, M. and Still, W. C., Proc. Natl. Acad. Sci. USA, 90 (1993) 10922.

    Article  CAS  Google Scholar 

  24. Muller, C., Kitas, E. and Wessel, H. P., J. Chem. Soc., Chem. Commun., 11 (1995) 2425.

    Article  Google Scholar 

  25. Nicolaou, K. C., Florke, H., Egan, M. G., Barth, T. and Estevez, V. A., Tetrahedron Lett., 36 (1995) 1775.

    Article  CAS  Google Scholar 

  26. Suhara, Y., Hildreth, J. E. K. and Ichikawa, Y., Tetrahedron Lett., 37 (1996) 1575.

    Article  CAS  Google Scholar 

  27. Kanie, O., Barresi, F., Ding, Y., Labbe, J., Otter, A., Forsberg, L. S., Ernst, B. and Hindsgaul, O., Angew. Chem., Int. Ed. Engl., 34 (1995) 2720.

    Google Scholar 

  28. Ding, Y., Kanie, O., Labbe, J., Palcic, M. M., Ernst, B. and Hindsgaul, O., In Alavi, A. and Axford, J. S. (Eds.) Glycoimmunology, Plenum, New York, NY, 1995, p. 261.

    Chapter  Google Scholar 

  29. Boons, G. -J., Heskamp, B. and flout, F., Angew. Chem., Int. Ed. Engl., 35 (1996) 2845.

    Google Scholar 

  30. Sutherlin, D. P. and Armstrong, R. W., J. Org. Chem., 62 (1997) 5267.

    Article  CAS  Google Scholar 

  31. Sofia, M. J., Mol. Div., 3 (1997) 75.

    Article  CAS  Google Scholar 

  32. Sofia, M. J., Drug Discos,. Today, 1 (1996) 27.

    CAS  Google Scholar 

  33. Meldal, M., Curr. Opin. Struct. Biol., 4 (1994) 710.

    Article  CAS  Google Scholar 

  34. Andrews, D. M. and Seale, P. W., Int. J. Pept. Protein Res., 42 (1993) 165.

    Article  CAS  Google Scholar 

  35. Vetter, D. and Gallop, M. A., Bioconj. Chem., 6 (1995) 316.

    Article  CAS  Google Scholar 

  36. Vetter, D., Tumelty, D., Singh, S. K. and Gallop, M. A., Angew. Chem., Int. Ed. Engl., 34 (1995) 60.

    Google Scholar 

  37. Vetter, D., Tate, E. M. and Gallop, M. A., Bioconj. Chem., 6 (1995) 319.

    Article  CAS  Google Scholar 

  38. Chan, T. Y., Chen, A., Allanson, N., Chen, R., Liu, D. and Sofia, M. J., Tetrahedron Lett., 37 (1996) 8097.

    Article  CAS  Google Scholar 

  39. Allanson, N., Chan, T. Y., Chen, A., Chen, R., Liu, D., Baizman, E., Mintz, C., Axelrod, H. and Sofia, M. J., 211th ACS National Meeting, Abstract No. 199, New Orleans, LA, U. S. A., March 24–28, 1996.

    Google Scholar 

  40. Jansson, A. M., Meldal, M. and Bock, K., Tetrahedron Lett., 31 (1990) 6991.

    Article  CAS  Google Scholar 

  41. Meldal, M. and Bock, K., Tetrahedron Lett., 31 (1990) 6987.

    Article  CAS  Google Scholar 

  42. Bielfeldt, T., Peters, S., Meldal, M., Bock, K. and Paulsen, H., Angew. Chem., Int. Ed. Engl., 31 (1992) 857.

    Google Scholar 

  43. Jansson, A. M., Meldal, M. and Bock, K., J. Chem. Soc., Perkin Trans. 1 (1992) 1699.

    Google Scholar 

  44. Reimer, K. B., Meldal, M., Kusumoto, S., Fukase, K. and Bock, K., J. Chem. Soc., Perkin Trans. 1 (1993) 925.

    Google Scholar 

  45. Christensen, M. K., Meldal, M. and Bock, K., J. Chem. Soc., Perkin Trans. 1 (1993) 1453.

    Google Scholar 

  46. Christiansen-Brams, I., Meldal, M. and Bock, K., J. Chem Soc., Perkin Trans. 1 (1993) 1461.

    Google Scholar 

  47. Jensen, K. J., Meldal, M. and Bock, K., J. Chem. Soc., Perkin Trans. 1 (1993) 2119.

    Google Scholar 

  48. Christensen, M. K., Meldal, M., Bock, K., Cordes, H., Mouritsen, S. and Elsner, H., J. Chem. Soc., Perkin Trans. 1 (1994) 1299.

    Google Scholar 

  49. Meldal, M., Auzanneau, F. -1., Hindsgaul, O. and Palcic, M. M., J. Chem. Soc., Chem. Commun., 10 (1994) 1849.

    Google Scholar 

  50. Paulsen, H., Bielfeldt, T., Peters, S., Meldal, M. and Bock, K., Liebigs Ann. Chem., 10 (1994) 369.

    Article  Google Scholar 

  51. Seitz, O. and Kunz, H., Angew. Chem., Int. Ed. Engl., 34 (1995) 803.

    Google Scholar 

  52. Polt, R., Szabo, L., Treiberg, J., Li, Y. and Hmby, V. J., J. Am. Chem. Soc., 114 (1992) 10249.

    Article  CAS  Google Scholar 

  53. Szabo, L, Li, Y. and Polt, R., Tetrahedron Lett, 32 (1991) 585.

    Article  CAS  Google Scholar 

  54. Broddefalk, J., Bergquist, K: E. and Kihlberg, J., Tetrahedron Lett., 37 (1996) 3011.

    Article  CAS  Google Scholar 

  55. Peters, S., Bielfeldt, T., Meldal, M., Bock, K. and Paulsen, H., J. Chem. Soc., Perkin Trans. 1 (1992) 1163.

    Google Scholar 

  56. Meldal, M., Bisgaard Holm, C., Bojesen, G., Jakobsen, M. H. and Holm, A., Int. J. Pept. Res., 41 (1993) 250.

    Article  CAS  Google Scholar 

  57. Rio-Anneheim, S., Paulsen, H., Melds!, M. and Bock, K., J. Chem. Soc., Perkin Trans. 1 (1995) 1071.

    Google Scholar 

  58. Frische, K., Meldal, M., Werdelin, O., Mouritsen, S., Jensen, T., Galli-Stampino, L. and Bock, K., J. Pept. Sci., 2 (1996) 212.

    CAS  Google Scholar 

  59. Sutherlin, D. P., Stark, T. M., Hughes, R. and Armstrong, R. W., J. Org. Chem., 61 (1996) 8350.

    Article  CAS  Google Scholar 

  60. Armstrong, R. W., Combs, A. P., Tempest, P. A., Brown, S. D. and Keating, T. A., Acc. Chem. Res., 29 (1996) 123.

    Article  CAS  Google Scholar 

  61. Gravert, D. J. and Janda, K. D., Chem. Rev., 97 (1997) 489.

    Article  CAS  Google Scholar 

  62. Park, W. K. C., Auer, M., Jaksche, H. and Wong, C. -H., J. Am. Chem. Soc., 118 (1996) 10150.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Sofia, M.J. (1999). Accessing carbohydrate-based combinatorial libraries through solid phase and solution phase approaches. In: Moos, W.H., Pavia, M.R. (eds) Annual Reports in Combinatorial Chemistry and Molecular Diversity. Annual Reports in Combinatorial Chemistry and Molecular Diversity, vol 2. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0735-0_6

Download citation

  • DOI: https://doi.org/10.1007/978-94-017-0735-0_6

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-90-481-5227-8

  • Online ISBN: 978-94-017-0735-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics