Advertisement

Synthesis of the β-amyloid fragment 5RHDSGY10 and its isomers

  • E. Yu. Aleshina
  • N. V. Pyndyk
  • A. A. Moisa
  • M. A. Sanzhakov
  • O. N. Kharybin
  • E. N. Nikolaev
  • E. F. Kolesanova
Experimental Studies

Abstract

The peptide RHDSGY, a fragment of the human β-amyloid Zn-binding site, and its isomers RH(D-Asp)SGY and RH(β-Asp)SGY have been obtained as amides by means of solid-phase synthesis and analyzed by HPLC and various mass spectrometric methods. The problem of low yield of the RHDSGY peptide and its isomers attributed to 9-fluorenylmethoxycarbonyl (Fmoc)-amino acids and/or formation of such side-products as RH(β-Asp)SGY (or RHDSGY during synthesis of RH(β-Asp)SGY) and RH(Asp-imide) SGY was solved via selection of individual reagents for removal of Fmoc groups from α-amino groups of the growing peptide chain.

Key words

β-amyloid solid-phase peptide synthesis β-Asp Fmoc-group removal 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Clippingdale, A.B., Wade, J.D., and Barrow, C.J., J. Pept. Sci., 2001, vol. 7, no. 5, pp. 227–249.CrossRefGoogle Scholar
  2. 2.
    Hardy, J., and Selkoe, D.J., Science, 2002, vol. 297(5580), pp. 353–356.CrossRefGoogle Scholar
  3. 3.
    Zirah, S., Kozin, S.A., Mazur, A.K., Blond, A., Cheminant, M., Segalas-Milazzo, I., Debey, P., and Rebuffat, S., J. Biol. Chem., 2006, vol. 281(4), pp. 2151–2161.CrossRefGoogle Scholar
  4. 4.
    Meyer-Luehmann, M., Coomaraswamy, J., Bolmont, T., Kaeser, S., Schaefer, C., Kilger, E., Neuenschwander, A., Abramowski, D., Frey, P., Jaton, A.L., Vigouret, J.M., Paganetti, P., Walsh, D.M., Mathews, P.M., Ghiso, J., Staufenbiel, M., Walker, L.C., and Jucker, M., Science, 2006, vol. 313(5794), pp. 1781–1784.CrossRefGoogle Scholar
  5. 5.
    Galasko, D., J. Alzheimers Dis., 2005, vol. 8(4), pp. 339–346.Google Scholar
  6. 6.
    Lloyd-Williams, P., Albericio, F., and Giralt, E., in Chemical Approaches to the Synthesis of Peptides and Proteins, New York: CRC Press LLC, 1997, p. 280.Google Scholar
  7. 7.
    Wade, J.D., Mathieu, M.N., Macris, M., and Tregear, G.W., Letters in Peptide Science, 2000, vol. 7(2), pp. 107–112(6).Google Scholar
  8. 8.
    Cebrian, J., Domingo, V., and Reig, F., J. Peptide Res., 2003, vol. 62, pp. 238–244.CrossRefGoogle Scholar
  9. 9.
    Becker, H., Domschke, G., Fanghanel, E. et al., Organicum (Russian translation), Moscow: Mir, 1992, vol. 2.Google Scholar
  10. 10.
    SynPhase Technical Notes (STN) 002-1, http://www.mimotopes.com.
  11. 11.
    Teixeira, A., Benckhuijsen, W.E., de Koning, P.E., Valentijn, A.R.P.M., and Drijfhout, J.W., Protein Pept. Lett., 2002, vol. 9, pp. 379–385.CrossRefGoogle Scholar
  12. 12.
    Gonzalez, L.J., Shimizu, T., Satomi, Y., Betancourt, L., Besada, V., Padron, G., Orlando, R., Shirasawa, T., Shimonishi, Y., and Takao, T., Rapid Commun. Mass Spectrom., 2000, vol. 14(22), pp. 2092–2102.CrossRefGoogle Scholar
  13. 13.
    Hyde, C., Johnson, T., Owen, D., Quibell, M., and Sheppard, R.C., Int. J. Pept. Protein Res., 1994, vol. 43, pp. 431–440.Google Scholar
  14. 14.
    Larsen, B.D. and Holm, A., Int. J. Pept. Protein Res., 1994, vol. 43(1), pp. 1–9.Google Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • E. Yu. Aleshina
    • 1
  • N. V. Pyndyk
    • 1
  • A. A. Moisa
    • 1
  • M. A. Sanzhakov
    • 1
  • O. N. Kharybin
    • 1
  • E. N. Nikolaev
    • 1
  • E. F. Kolesanova
    • 1
  1. 1.Orekhovich Institute of Biomedical ChemistryRussian Academy of Medical SciencesMoscowRussia

Personalised recommendations