About this Journal Submit a Manuscript Table of Contents
International Journal of Carbohydrate Chemistry
Volume 2010 (2010), Article ID 594247, 8 pages
Research Article

Koenigs-Knorr Glycosylation with Neuraminic Acid Derivatives

1Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow 117997, Russia
2Biochemistry Center Heidelberg, University of Heidelberg, 69120 Heidelberg, Germany

Received 13 July 2010; Revised 15 September 2010; Accepted 21 October 2010

Academic Editor: Richard D. Cummings

Copyright © 2010 Galina Pazynina et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Schauer, “Achievements and challenges of sialic acid research,” Glycoconjugate Journal, vol. 17, no. 7-9, pp. 485–499, 2000. View at Publisher · View at Google Scholar
  2. A. Varki, “Sialic acids in human health and disease,” Trends in Molecular Medicine, vol. 14, no. 8, pp. 351–360, 2008. View at Publisher · View at Google Scholar · View at PubMed
  3. G.-J. Boons and A. V. Demchenko, “Recent advances in O-sialylation,” Chemical Reviews, vol. 100, no. 12, pp. 4539–4565, 2000. View at Publisher · View at Google Scholar
  4. R. L. Halcomb and M. D. Chappell, “Recent developments in technology for glycosylation with sialic acid,” Journal of Carbohydrate Chemistry, vol. 21, no. 7–9, pp. 723–768, 2002. View at Publisher · View at Google Scholar
  5. Y. Liu, X. Ruan, X. Li, and Y. Li, “Efficient synthesis of a sialic acid α(2→3)galactose building block and its application to the synthesis of ganglioside GM3,” Journal of Organic Chemistry, vol. 73, no. 11, pp. 4287–4290, 2008. View at Publisher · View at Google Scholar · View at PubMed
  6. G. Pazynina, A. Tuzikov, A. Chinarev, P. Obukhova, and N. Bovin, “Simple stereoselective synthesis of α2-6 sialooligosaccharides,” Tetrahedron Letters, vol. 43, no. 45, pp. 8011–8013, 2002. View at Publisher · View at Google Scholar
  7. T. Yamaji, T. Teranishi, M. S. Alphey, P. R. Crocker, and Y. Hashimoto, “A small region of the natural killer cell receptor, Siglec-7, is responsible for its preferred binding to α2,8-disialyl and branched α2,6-sialyl residues. A comparison with Siglec-9,” Journal of Biological Chemistry, vol. 277, no. 8, pp. 6324–6332, 2002. View at Publisher · View at Google Scholar · View at PubMed
  8. L. A. Simeoni, A. B. Tuzikov, N. E. Byramova, and N. V. Bovin, “Neu5Ac and Neu5Gc ethylthioglycoside derivatives as glycosyl donors. Synthesis of aminopropyl glycosides of N-acetyl and N-glycolylneuraminic acid,” Russian Journal of Bioorganic Chemistry, vol. 23, pp. 139–146, 1997.
  9. A. Hasegawa, H. Ishida, and M. Kiso, “Synthetic studies on sialoglycoconjugates 46: a facile total synthesis of ganglioside GD3,” Journal of Carbohydrate Chemistry, vol. 12, pp. 371–376, 1993.
  10. H. Ando, H. Ishida, M. Kiso, and A. Hasegawa, “A synthetic approach to the c-series gangliosides containing sialyl-α(2 → 8) sialyl-α(2 → and) sialic acid: synthesis of ganglioside GT4, α(2 → 6) GT4 and GT3,” Carbohydrate Research, vol. 300, no. 3, pp. 207–217, 1997. View at Publisher · View at Google Scholar
  11. A. B. Tuzikov, A. S. Gambaryan, L. R. Juneja, and N. V. Bovin, “Conversion of complex sialooligosaccharides into polymeric conjugates and their anti-influenza virus inhibitory potency,” Journal of Carbohydrate Chemistry, vol. 19, no. 9, pp. 1191–1200, 2000.
  12. S. Z. Abbas, S. Sugiyama, J. Diakur, R. A. Pon, and R. Roy, “Synthesis of α- and β-methyl Neu5Acα-(2→8)Neu5Ac disaccharides,” Journal of Carbohydrate Chemistry, vol. 9, no. 6, pp. 891–901, 1990.
  13. A. A. Sherman, O. N. Yudina, A. S. Shashkov, V. M. Menshov, and N. E. Nifant'ev, “Synthesis of Neu5Ac- and Neu5Gc-α-(26)-lactosamine 3-aminopropyl glycosides,” Carbohydrate Research, vol. 330, no. 4, pp. 445–458, 2001. View at Publisher · View at Google Scholar
  14. H. J. Gross, A. Bünsch, J. C. Paulson, and R. Brossmer, “Activation and transfer of novel synthetic 9-substituted sialic acids,” European Journal of Biochemistry, vol. 168, no. 3, pp. 595–602, 1987.
  15. F. Michon, J.-R. Brisson, and H. J. Jennings, “Conformational differences between linear α(28)-linked homosialooligosaccharides and the epitope of the group B meningococcal polysaccharide,” Biochemistry, vol. 26, no. 25, pp. 8399–8405, 1987.
  16. E. M. Rapoport, G. V. Pazynina, M. A. Sablina, P. R. Crocker, and N. V. Bovin, “Probing sialic acid binding Ig-like lectins (siglecs) with sulfated oligosaccharides,” Biochemistry, vol. 71, no. 5, pp. 496–504, 2006. View at Publisher · View at Google Scholar
  17. O. A. Kost, N. V. Bovin, E. E. Chemodanova, V. V. Nasonov, and T. A. Orth, “New feature of angiotensin-converting enzyme: carbohydrate-recognizing domain,” Journal of Molecular Recognition, vol. 13, no. 6, pp. 360–369, 2000.
  18. E. M. Rapoport, YU. B. Sapot'ko, G. V. Pazynina, V. K. Bojenko, and N. V. Bovin, “Sialoside-binding macrophage lectins in phagocytosis of apoptotic bodies,” Biochemistry, vol. 70, no. 3, pp. 330–338, 2005. View at Publisher · View at Google Scholar
  19. R. Brossmer and H. J. Gross, “Sialic acid analogs and application for preparation of neoglycoconjugates,” Methods in Enzymology, vol. 247, pp. 153–176, 1994. View at Publisher · View at Google Scholar · View at Scopus