Pharmaceutical Research

, Volume 5, Issue 8, pp 523–527 | Cite as

Formulation of Vaccine Adjuvant Muramyldipeptides (MDP). 1. Characterization of Amorphous and Crystalline Forms of a Muramyldipeptide Analogue

  • Tai Wah Chan
  • Allyn Becker


A relatively nonhygroscopic crystalline form of the glycopeptide, N-acetylmuramyl-L-α-aminobu-tyryl-D-isoglutamine (I), containing approximately one molecule of water was prepared from amorphous material. The crystalline material, consisting of a mixture of the α and β anomers, exhibited better physical and chemical stability than the lyophilized amorphous material. The α/β-anomer ratios of I in both the crystalline and the amorphous state were approximately equal but different from that in solution.

muramyldipeptide hydrate crystalline modification mutarotation 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    F. Ellouz, A. Adam, R. Ciorbaru, and E. Lederer. Biochem. Biophys. Res. Comm. 59:1317–1325 (1974).Google Scholar
  2. 2.
    C. Merser and P. Sinay. Biochem. Biophys. Res. Comm. 66:1316–1322 (1975).Google Scholar
  3. 3.
    S. Kotani, Y. Watanabe, F. Kinoshita, T. Shimono, I. Morisaki, T. Shiba, S. Kusumoto, Y. Tarumi, and K. Ikenaka. Biken J. 18:105–111 (1975).Google Scholar
  4. 4.
    S. Kotani, F. Kinoshita, I. Morisaki, T. Shimono, T. Okunaga, H. Takada, M. Tsujimoto, Y. Watanabe, K. Kato, S. Shiba, S. Kusumoto, and S. Okada. Biken J. 20:95–103 (1977).Google Scholar
  5. 5.
    L. Chedid and E. Lederer. Biochem. Pharmacol. 27:2183–2186 (1978).Google Scholar
  6. 6.
    A. Hasegawa, H. Okumura, H. Kiso, M. Kiso, I. Azuma, and Y. Yamamura. Agr. Biol. Chem. 44:1301–1308 (1980).Google Scholar
  7. 7.
    A. Hasegawa, H. Okumura, M. Kiso, I. Azuma, and Y. Yamamura. Agr. Biol. Chem. 44:1309–1313 (1980).Google Scholar
  8. 8.
    A. Hasegawa, Y. Hioki, M. Kiso, H. Okumura, and I. Azuma. Carbohydr. Res. 123:183–199 (1983).Google Scholar
  9. 9.
    A. Adam, M. Devys, V. Souvannavong, P. LeFrancier, J. Choay, and E. Lederer. Biochem. Biophys. Res. Commun. 72:339–346 (1976).Google Scholar
  10. 10.
    S. Kobayashi, T. Fukuda, I. Imada, M. Fujino, I. Azuma, and Y. Yamamura. Chem. Pharm. Bull. 27:3193–3196 (1979).Google Scholar
  11. 11.
    S. Kobayashi, T. Fukuda, H. Yukimasa, M. Fujino, I. Azuma, and Y. Yamamura. Bull. Chem. Soc. Jpn. 53:2570–2577 (1980).Google Scholar
  12. 12.
    G. Jones, J. Moffat, and J. Nestor. Ger. Pat. No. 2718010.Google Scholar
  13. 13.
    T. D. J. Halls, M. S. Raju, E. Wenkert, M. Zubu, P. Lefrancier, and E. Lederer. Carbohydr. Res. 81:173–176 (1980).Google Scholar
  14. 14.
    B. E. Chapman, M. Batley, and J. Redmond. Aust. J. Chem. 35:489–493 (1982).Google Scholar
  15. 15.
    H. Okumura, I. Azuma, M. Kiso, and A. Hasegawa. Carbohydr. Res. 117:298–303 (1983).Google Scholar
  16. 16.
    E. F. McFarland and C. Martinic. Aust. J. Chem. 36:1087–1096 (1983).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • Tai Wah Chan
    • 1
  • Allyn Becker
    • 1
  1. 1.Institute of Pharmaceutical SciencesSyntex ResearchPalo Alto

Personalised recommendations