Advertisement

Research on Chemical Intermediates

, Volume 36, Issue 3, pp 237–243 | Cite as

Facile synthesis of chiral N-glycosylated amino acids

  • Lin Fa Wang
  • Ling Qiang Kong
  • Li Fan
  • Da Cheng Yang
Article

Abstract

Five designed chiral glycosylated amino acids have been synthesized for the first time by coupling of 1,3,4,6-tetra-O-acetyl-β-D-glucosamine sulfate (2), previously prepared by direct acetylation of D-glucosamine hydrochloride with acetic anhydride, with chiral Fmoc-protected amino acids and DIC, HOBt, and DIEA under mild conditions. The structures of these new compounds were characterized by IR, 1H NMR, and 13C NMR spectroscopy and ESI MS.

Keywords

N-Glycosylated amino acid Fmoc-protected amino acid Glucosamine Chiral 

References

  1. 1.
    A. Varki, Glycobiology 3, 97 (1993)CrossRefGoogle Scholar
  2. 2.
    H. Hojo, Y. Nakahara, Curr. Prot. Pept. Sci. 1, 23 (2000)CrossRefGoogle Scholar
  3. 3.
    R. Polt, M.M. Palian, Drugs Future 26, 561 (2001)CrossRefGoogle Scholar
  4. 4.
    R. Polt, F. Porreca, L.Z. Szabo, E.J. Bilsky, P. Davis, T.J. Abbruscato, T.P. Davis, R. Horvath, H.I. Yamamura, V.J. Hruby, Proc. Natl. Acad. Sci. USA 91, 7114–7118 (1994)CrossRefGoogle Scholar
  5. 5.
    E.J. Bilsky, R.D. Egleton, S.A. Mitchell, M.M. Palian, P. Davis, J.D. Huber, H. Jones, H.I. Yamamura, J. Janders, T.P. Davis, F. Porreca, V.J. Hruby, R. Polt, J. Med. Chem. 43, 2586 (2000)CrossRefGoogle Scholar
  6. 6.
    R.D. Egleton, S.A. Mitchell, J.D. Huber, M.M. Palian, R. Polt, T.P. Davis, J. Pharmacol. Exp. Ther. 299, 967 (2001)Google Scholar
  7. 7.
    J.Y. Reginster, R. Deroisy, L.C. Rovati, R.L. Lee, E. Lejeune, O. Bruyere, G. Glacovelli, Y. Henrotin, J.E. Dacre, C. Gossett, Lancet 357, 251 (2001)CrossRefGoogle Scholar
  8. 8.
    B.G. Donzelli, G. Ostroff, G.E. Harman, Carbohydr. Res. 338, 1823 (2003)CrossRefGoogle Scholar
  9. 9.
    S. Hanessian, Tetrahedron Lett. 16, 1549 (1967)CrossRefGoogle Scholar
  10. 10.
    I. Yoshiyuki, O. Konoshin, K. Shozaburo et al., J. Am. Chem. Soc. 79, 4218 (1957)CrossRefGoogle Scholar
  11. 11.
    M. Avalos, R. Babiano, P. Cintas et al., J. Chem. Soc., Perkin Trans. 1, 495 (1990)CrossRefGoogle Scholar
  12. 12.
    M. Bergmann, L. Zervas, J. Chem. Ber. 64, 973 (1931)Google Scholar
  13. 13.
    X.U. Jin-feng, F. Zhi-jie, J. Chang-li, Chin. J. Synth. Chem. 11, 379 (2003)Google Scholar
  14. 14.
    L. Yongcheng, W. Zhicai, Chin. J. Mar. Drugs 59, 1 (1996)Google Scholar
  15. 15.
    G. Rui-xia, L. Wei, F. Zhi-jie, C. Xiao-bing, G. Jian, Chin. J. Synth. Chem. 12 (1), 6 (2004)Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  • Lin Fa Wang
    • 1
  • Ling Qiang Kong
    • 1
  • Li Fan
    • 1
  • Da Cheng Yang
    • 1
  1. 1.College of Chemistry and Chemical EngineeringSouthwest UniversityChongqingChina

Personalised recommendations