Skip to main content
Log in

Facile synthesis of chiral N-glycosylated amino acids

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

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.

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.

Institutional subscriptions

Scheme 1
Scheme 2

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. H. Hojo, Y. Nakahara, Curr. Prot. Pept. Sci. 1, 23 (2000)

    Article  CAS  Google Scholar 

  3. R. Polt, M.M. Palian, Drugs Future 26, 561 (2001)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  8. B.G. Donzelli, G. Ostroff, G.E. Harman, Carbohydr. Res. 338, 1823 (2003)

    Article  CAS  Google Scholar 

  9. S. Hanessian, Tetrahedron Lett. 16, 1549 (1967)

    Article  CAS  Google Scholar 

  10. I. Yoshiyuki, O. Konoshin, K. Shozaburo et al., J. Am. Chem. Soc. 79, 4218 (1957)

    Article  Google Scholar 

  11. M. Avalos, R. Babiano, P. Cintas et al., J. Chem. Soc., Perkin Trans. 1, 495 (1990)

    Article  Google Scholar 

  12. M. Bergmann, L. Zervas, J. Chem. Ber. 64, 973 (1931)

    Google Scholar 

  13. X.U. Jin-feng, F. Zhi-jie, J. Chang-li, Chin. J. Synth. Chem. 11, 379 (2003)

    Google Scholar 

  14. L. Yongcheng, W. Zhicai, Chin. J. Mar. Drugs 59, 1 (1996)

    Google Scholar 

  15. G. Rui-xia, L. Wei, F. Zhi-jie, C. Xiao-bing, G. Jian, Chin. J. Synth. Chem. 12 (1), 6 (2004)

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Da Cheng Yang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, L.F., Kong, L.Q., Fan, L. et al. Facile synthesis of chiral N-glycosylated amino acids. Res Chem Intermed 36, 237–243 (2010). https://doi.org/10.1007/s11164-010-0133-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-010-0133-6

Keywords

Navigation