Cyclic Analogue of Human Heat Shock Protein 70(29-42) Fragment. Synthesis, Conformational Studies and Evaluation of Its Immunogenicity

• Autorzy: Karawajczyk B. , Wirkus-Romanowska I. , Wysocki J. , Rolka K. , Maćkiewicz Z. , Głośnicka R. , Kupryszewski G.
• Języki publikacji: EN

Abstrakty

EN

The cyclic hexadecapeptide containing human heat shock protein 70(29-42) fragment cyclized by the disulfide bridge between two L-cysteine residues introduced at the N- and C-termini was synthesized by the solid phase method. It was established that the cyclic analogue, contrary to its linear counterpart, had much lower ability to generate immune response in rabbits. Conformational studies of cyclic peptide performed using 1D and 2D 1H-NMR spectroscopy in conjunction with theoretical conformational analysis revealed that the cyclization constrained the 3D structure of this peptide, reflected by the observed rate of cis/trans isomerization of Arg9-Thr10 peptide bond and the presence of Gly7-Asn8 peptide bond in cis geometry.We, therefore, postulate that the conformational flexibility in the case of Human Heat Shock Protein fragments is a key element for their immunogenicity.

Słowa kluczowe

EN

solid phase peptide synthesis; cyclic analogue of human heat shoc protein70 fragment; immunogenicity; conformational studies; 2D NMR

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 2
• Strony: 265--273
• Opis fizyczny: Bibliogr. 16 poz., rys.

Twórcy

autor

Karawajczyk B.

• Faculty of Chemistry, University of Gdansk, 80-952 Gdansk, Poland

autor

Wirkus-Romanowska I.

• Faculty of Chemistry, University of Gdansk, 80-952 Gdansk, Poland

autor

Wysocki J.

• Institute of Maritime and Tropical Medicine, 80-915 Gdynia, Poland

autor

Rolka K.

• Faculty of Chemistry, University of Gdansk, 80-952 Gdansk, Poland

autor

Maćkiewicz Z.

• Faculty of Chemistry, University of Gdansk, 80-952 Gdansk, Poland

autor

Głośnicka R.

• Institute of Maritime and Tropical Medicine, 80-915 Gdynia, Poland

autor

Kupryszewski G.

• Faculty of Chemistry, University of Gdansk, 80-952 Gdansk, Poland

Bibliografia

• 1. Lindquist S., Ann. Rev. Biochem., 55, 1151 (1986).
• 2. Skowyra Z. and Żylicz M., Post. Bioch,, 33, 259 (1987).
• 3. Lipińska B., Post. Bioch., 36, 32 (1990).
• 4. Karawajczyk B., Wysocki J., Kunikowska D,, Mackiewicz Z., Głośnicka R., Korzeniowski A., Górski J. and Kupryszewski G., Polish J. Chem., 72, 1017 (1998).
• 5. Rizo J. and Gierasch L.M., Ann. Rev. Biochem., 61, 387 (1992).
• 6. Barany B.F. and Merrifield R.B., The Peptides Analysis, Synthesis, Biology. Vol. 2, (Eds. Gross E. and Mainenhofer J.), Acad. Press, N Y, 1980, p. 3.
• 7. Gism B.F., Helv. Chim. Acta, 56, 1476 (1973).
• 8. Kaiser E., Colescoft R,, Bossinger C.D. and Cool P.J., Anal Biochem., 34, 595 (1977).
• 9. Tam J.P., Health W.F. and Merrifield R.B., J. Am. Chem. Soc., 105, 6442 (1983).
• 10. Veber D.F., Milkowski J.D., Varga S., Denkewalter R.G. and Hirschmann R., J. Am. Chem. Soc., 94, 5456 (1972).
• 11. Kamber B., Helv, Chim. Acta, 54, 927 (1971),
• 12. Bruenger A., X-PLOR 3.2, Yale Univ. Press, New Haven (1993).
• 13. Brooks B., Bruccoleri R., Olafson B.O., States D.J., Swaminathan S. andKarplusM., J. Comp. Chem.,4, 187(1993).
• 14. Powell M.J.D., Math. Prog., 12, 241 (1977).
• 15. Lewis P.N., Momany F.A. and Scheraga H.A., Biochim. Biophys. Acta, 303, 211 (1973).
• 16. Cresswell P. and Howard J., Curr. Opin Immunol, 11, 61 (1999).