Difficulties in synthesis and characterization of viral capsid peptides

Difficulties in synthesis and characterization of viral capsid peptides

Peptides and proteins play a central role in numerous biological and physiological processes in living organisms. Viral capsid pepdides are part of the viruses outer shell of genetic materials. Viruses are recognized by immune system via capsid peptides. Depending on this property of capsid peptides, totally synthetic vaccine prototypes can be developed. In this work we synthesised 3 different viral peptide sequences with microwave enhanced Solid Phase Peptide Synthesis (SPPS) method and characerized with LC-ESI-MS system. We briefly describe the difficulties in synthesis and characterization.

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  • 1. Fischer, E. & Fourneau, E. (1901) Ueber einige Derivate des Glykokolls. Ber. Dtsch. Chem. Ges. 34, 2868–2879.
  • 2. Curtius, T. (1882) Ueber einige neue Hippursa¨ureanalog constituierte synthetisch dargestellte Aminosa¨uren. J. Prakt. Chemie 26, 145–208.
  • 3. Kimmerlin, T. & Seebach, D. ‘100 years of peptide synthesis’: ligation methods for peptide and protein synthesis with applications to bpeptide assemblies. J. Peptide Res., 2005, 65, 229–260.
  • 4. Merrifield, R. B. Solid Phase Synthesis. Nobel lecture, 8 December, 1984, The Rockefeller University, 1230 York Avenue, New York, N.Y. 10021-6399
  • 5. Merrifield, R. B. (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149–2154.
  • 6. Carpino, L.A. (1957) Oxidative reactions of hydrazines. IV. Elimination of nitrogen from 1,1- disubstituted-2-arensulfonhydrazides. J. Am. Chem. Soc. 79, 4427–4430.
  • 7. McKay, F.C. & Albertson, N.F. (1957) New amine-masking groups for peptide synthesis. J. Am. Chem. Soc. 79, 4686–4690.
  • 8. Carpino, L.A. & Han, G.Y. (1970) The 9- fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group. J. Am. Chem. Soc. 92, 5748–5749.
  • 9. Palese P (2006). “Making better influenza virus vaccines?”. Emerging Infect. Dis. 12 (1): 61–5.
  • 10. Alberts, B., Bray, D., Lewis, J., Raff, M., Roberts, K., Watson, J. D., (1994). Molecular Biology of the Cell, 4, 280.
  • 11. Petrov R. V., Mustafaev, M. I., Norimov A., Physicochemical criteria for the construction of artificial immunomodulators and immunogens on the basis of polyelectrolyte complexes. In: Sov Med Rev D Immunol. UK: Harwood Academic Publishers GmbH; 1992. p. 1–113.
  • 12. Mustafaev M., , “Functionally Biopolymer Systems”, Sigma Journal of Engineering and Natural Science, 4, 2004, pp. 1-201.
  • 13. van Lierop, M. J. C., Wagenaar, J.A., van Noort, J.M., Hensen, E.J., Journal of Virology, 1995, 69, p. 4511–4514.
  • 14. Yedidia, T. B., Arnon, R., Synthetic peptidebased vaccines against influenza,1997, International Journal of Peptide Research and Therapeutics.
  • 15. Chapman, J.R. (2000) Mass Spectrometry of Proteins and Peptides. Sale, Manchester, UK.
  • 16. Chakraborty, A. B. and Berger, S. J., Optimization of Reversed-Phase Peptide Liquid Chromatography Ultraviolet Mass Spectrometry Analyses Using an Automated Blending Methodology, Journal of Biomolecular Techniques 16:325–333, 2005 ABRF
  • 17. Aguilar, M.-I. (2004) HPLC of Peptides and Proteins: Methods and Protocols. Monash University, Clayton, Victoria, Australia.
  • 18. Kappe, C. O. “Controlled microwave heating in modern organic synthesis.” Angew. Chem. Int. Ed. 2004, 43, 6250.
  • 19. Kappe, C. O.; Stadler, A. “Microwaves in organic and medicinal chemistry”, Wiley-VCH, 2005.