Skip to main content
Log in

Synthesis and activity of phosphono desmuramyldipeptide analogs

  • Section II. Synthesis and Libraries
  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

Summary

Two phosphono desmuramyldipeptide analogs, 6 and 11, were synthesized and evaluated for immunomodulatory activity. Phthalimido-and adamantyl-substituted side chains as a replacement for the N-acetylmuraminic acid were coupled with appropriate dipeptides using DPPA as the coupling reagent. Introduction of a phosphonamidate moiety in compound 6 resulted in lower biological activity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Ellouz, F., Adam, A., Ciobaru, R. and Lederer, E., Biochem. Biophys. Res. Commun., 59 (1974) 1317.

    Google Scholar 

  2. Urleb, U., Krbavčič, A., Sollner, M., Kikelj, D. and Pečar, S., Arch. Pharm., 328 (1995) 113.

    Google Scholar 

  3. Pečar, S., Urleb, U., Sollner, M., Kikelj, D., Marc, G., Krbavčič, A., Kotnik, V., Wraber-Herzog, B., Simčič, S., Ihan, A., Klamfer, L., Kopitar, Z. and Štalc, A., European Patent application 91 116 356.6 (1991).

  4. Hilderbrand, R.L. (Ed.) The Role of Phosphonates in Living Systems, CRC Press, Boca Raton, FL, 1983.

    Google Scholar 

  5. Engel, R. (Ed.) Handbook of Organophosphorus Chemistry, Marcel Dekker, Inc., New York, NY, 1992.

    Google Scholar 

  6. Yamauchi, K., Kinoshita, M. and Imoto, M., Bull. Chem. Soc. Jpn., 45 (1972) 2531.

    Google Scholar 

  7. Kusumoto, S., Tarumi, Y., Ikenaka, K. and Shiba, T., Bull. Chem. Soc. Jpn., 49 (1976) 533.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Urleb, U., Gobec, S. & Prelog, D. Synthesis and activity of phosphono desmuramyldipeptide analogs. Lett Pept Sci 2, 193–197 (1995). https://doi.org/10.1007/BF00119151

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00119151

Keywords

Navigation