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Synthesis and evaluation of N-acetylneuraminic acid-based affinity matrices for the purification of sialic acid-recognizing proteins

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Abstract

The synthesis of 2-S-(2-aminoethyl) 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidon ic acid (1) has been successfully achieved from the precursors methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosonate (2) and 2-bromo-N-(tert-butoxycarbonyl)-ethylamine (5). Compounds 1 and 2 were coupled, via amino and thioglycosidic linkages, respectively, to epoxy-activated Sepharose 6B. The resultant affinity adsorbents have proved efficient in purifying the sialic acid-recognizing enzyme Vibrio cholerae sialidase, in a one-step process with yields in the order of 60%.

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References

  1. Schauer R (1985) Trends Biochem Sci 10: 357-60.

    Google Scholar 

  2. Roggentin P, Schauer R, Hoyer LL, Vimr ER (1993) Mol Microbiol 9: 915-21.

    Google Scholar 

  3. Liu DY, Petschek KD, Remold HG, David JR (1982) J Biol Chem 257: 159-62.

    Google Scholar 

  4. Schengrund CL, Jensen DS, Rosenberg A (1972) J Biol Chem 247: 2742-6.

    Google Scholar 

  5. Suzuki J, Murakami K, Nishimura Y (1993) J Carbohydr Chem 12: 201-8.

    Google Scholar 

  6. Reinhard B, Götz C, Faillard H (1992) Biol Chem Hoppe-Seyler 373: 1243-8.

    Google Scholar 

  7. Schauer R, Wember M (1989) Biol Chem Hoppe-Seyler 370: 183-90.

    Google Scholar 

  8. Glasgow LR, Paulson JC, Hill RL (1977) J Biol Chem 252: 8615-23.

    Google Scholar 

  9. Crampen M, von Nicolai H, Zilliken F (1979) Hoppe-Seyler's Z Physiol Chem 360: 1703-12.

    Google Scholar 

  10. Ohta Y, Tsukada Y, Sugimori T (1989) J Biochem 106: 1086-9.

    Google Scholar 

  11. Narayanan SR (1994) J Chromatogr A 658: 237-58.

    Google Scholar 

  12. Holmquist L (1974) Acta Chem Scand Ser B 28: 1065-8.

    Google Scholar 

  13. Holmquist L, Östman B (1975) FEBS Lett 60: 327-30.

    Google Scholar 

  14. van Dessel G, De Wolf M, Lagrou A, Hilderson H, Dierick W (1984) J Biochem 96: 937-47.

    Google Scholar 

  15. Michalski J-C, Corfield AP, Schauer R (1982) Hoppe-Seyler's Z Physiol Chem 363: 1097-1102.

    Google Scholar 

  16. Geisow MJ (1975) Biochem J 151: 181-3.

    Google Scholar 

  17. Corfield AP, Parker TL, Schauer R (1979) Anal Biochem 100: 221-32.

    Google Scholar 

  18. Brossmer R, Ziegler D, Keilich G (1977) Hoppe-Seyler's Z Physiol Chem 358: 397-400.

    Google Scholar 

  19. Cuatrecasas P, Illiano G (1971) Biochem Biophys Res Commun 44: 178-84.

    Google Scholar 

  20. Suzuki Y, Sato K, Kiso M, Hasegawa A (1990) Glycoconjugate J 7: 349-56.

    Google Scholar 

  21. Chong AKJ, Pegg MS, von Itzstein M (1991) Biochim Biophys Acta 1077: 65-71.

    Google Scholar 

  22. Tiralongo J, Pegg MS, von Itzstein M (1995) FEBS Lett 372: 148-50.

    Google Scholar 

  23. Bennett S, von Itzstein M, Kiefel MJ (1994) Carbohydr Res 259: 293-9.

    Google Scholar 

  24. Kiefel MJ, Beisner B, Bennett S, Holmes ID, von Itzstein M (1996) J Med Chem 39: 1314-20.

    Google Scholar 

  25. Angus DI, von Itzstein M (1995) Carbohydr Res 274: 279-83.

    Google Scholar 

  26. Smalec B, von Itzstein M (1995) Carbohydr Res 266: 269-72.

    Google Scholar 

  27. Hasegawa A, Nakamura J, Kiso M(1986) J Carbohydr Chem 5: 11-19.

    Google Scholar 

  28. Myers RW, Lee RT, Lee YC, Thomas GH, Reynolds LW, Uchida Y (1980) Anal Biochem 101: 166-74.

    Google Scholar 

  29. Vimr ER, Lawrisuk L, Galen J, Kaper JB (1988) J Bacteriol 170: 1495-504.

    Google Scholar 

  30. Taylor G, Vimr E, Garman E, Laver G (1992) J Mol Biol 226: 1287-90.

    Google Scholar 

  31. Potier M, Mameli L, Belisle M, Dallaire L, Melancon SB (1979) Anal Biochem 94: 287-96.

    Google Scholar 

  32. Holzer CT, von Itzstein M, Jin B, Pegg MS, Stewart WP, Wu W-Y (1993) Glycoconjugate J 10: 40-4.

    Google Scholar 

  33. Silverstein RM, Bassler GC, Morrill TC (1991) Spectrometric Identification of Organic Compounds, 5th ed. New York: Wiley.

    Google Scholar 

  34. Warner TG, Lee LA (1988) Carbohydr Res 176: 211-18.

    Google Scholar 

  35. Crennel S, Garmen E, Taylor G (1994) Structure 2: 535-44.

    Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Medicinal Chemistry, Monash University (Parkville Campus), 381 Royal Parade, Parkville, 3052, Victoria, Australia

    Silvana Ciccotosto, Milton J Kiefel, Samia Abo, Wendy Stewart, Kaylene Quelch & Mark von Itzstein

Authors
  1. Silvana Ciccotosto
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  2. Milton J Kiefel
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  3. Samia Abo
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  4. Wendy Stewart
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  5. Kaylene Quelch
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  6. Mark von Itzstein
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Ciccotosto, S., Kiefel, M.J., Abo, S. et al. Synthesis and evaluation of N-acetylneuraminic acid-based affinity matrices for the purification of sialic acid-recognizing proteins. Glycoconj J 15, 663–669 (1998). https://doi.org/10.1023/A:1006932330367

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