Russian Chemical Bulletin

, Volume 63, Issue 2, pp 507–510 | Cite as

Synthesis of N-glycyl-β-glycopyranosyl amines, derivatives of natural oligosaccharides — glucose analogs of Lex antigen

  • L. M. Likhosherstov
  • O. S. Novikova
  • N. G. Kolotyrkina
  • I. A. Yamskov
  • V. E. Piskarev
Full Articles


Treatment of the natural tri-, tetra-, and pentasaccharides, β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp, α-l-Fucp-(1→2)-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp, and α-l-Fucp-(1→2)-[α-d-GalNAcp-(1→3)]-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp, which are glucose analogs of Lex, with ammonium carbamate in aqueous methanol gave the corresponding β-glycopyranosyl amines. After their N-acylation with N-Z-glycine N-hydroxysuccinimidyl ester (Z is benzyloxycarbonyl) with subsequent hydrogenolytic removal of Z-group, corresponding N-glycyl-β-glycopyranosyl amines were obtained in yields up to 70%.


β-glycopyranosyl amines oligosaccharides human milk human urine α-l-fucose glucose analog of Lex antigen N-acylation N-glycyl-β-glycopyranosyl amines 


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • L. M. Likhosherstov
    • 1
  • O. S. Novikova
    • 1
  • N. G. Kolotyrkina
    • 1
  • I. A. Yamskov
    • 2
  • V. E. Piskarev
    • 2
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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