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Synthesis of antiparallel 4α-helix bundle TASP by chemoselective ligation

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Summary

The use of chemoselective ligation methods and orthogonal protection techniques allows access to Template-Assembled Synthetic Protein (TASP) molecules exhibiting a large variety of packing topologies. This is demonstrated for the synthesis of an antiparallel 4α-helical bundle TASP by condensing amphiphilic peptide blocks, containing aldehyde functions at the C- or N-terminus, to a selectively addressable topological template via oxime bond formation. The resulting antiparallel 4α-helix TASP is obtained in high yield and shows a template-induced helical conformation.

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References

  1. Mutter, M., In Marshall, G.R. (Ed.) Peptides: Chemistry and Biology (Proceedings of the 10th American Peptide Symposium), ESCOM, Leiden, 1988, pp. 349–353.

    Google Scholar 

  2. Mutter, M., Trends Biochem. Sci., 13 (1988) 260.

    Google Scholar 

  3. Mutter, M. and Vuilleumier, S., Angew. Chem., Int. Ed. Engl., 28 (1989) 535.

    Google Scholar 

  4. Vilaseca, L.A., Rose, K., Werlen, R., Meunier, A. and Offord, R.E., Bioconj. Chem., 4 (1993) 515.

    Google Scholar 

  5. Rose, K., J. Am. Chem. Soc., 116 (1994) 30.

    Google Scholar 

  6. Dawson, P.E. and Kent, S.B.H., J. Am. Chem. Soc., 115 (1993) 7263.

    Google Scholar 

  7. Tuchscherer, G., Tetrahedron Lett., 34 (1993) 8419.

    Google Scholar 

  8. Robey, F.A. and Fields, R.I., Anal. Biochem., 177 (1989) 373.

    Google Scholar 

  9. Tuchscherer, G., Ernest, I., Rose, K. and Mutter, M., In Hodges, R.S. and Smith, J.A. (Eds.) Peptides (Proceedings of the 13th American Peptide Symposium), ESCOM, Leiden, 1994, pp. 1067–1068.

    Google Scholar 

  10. 10.Bodanszky, M. (Ed.) Principles of Peptide Synthesis, Springer Verlag, Heidelberg, 1984.

    Google Scholar 

  11. Ernest, I., Kalvoda, J., Sigel, C., Rihs, G., Fritz, H., Blommers, M.J.J., Raschdorf, F., Francotte, E. and Mutter, M., Helv. Chim. Acta, 76 (1993) 1539.

    Google Scholar 

  12. Stewart, J.M. and Young, J.D. (Eds.) Solid Phase Peptide Synthesis, 2nd ed., Pierce Chemical Co., Rockford, IL, 1984.

    Google Scholar 

  13. Sheppard, R.C. and Williams, B.J., J. Chem. Soc., Chem. Commun., (1982) 587.

  14. Rink, H., Tetrahedron Lett., 28 (1987) 3787.

    Google Scholar 

  15. Danglas, O., Guibé, F. and Balavoine, G., J. Org. Chem., 52 (1987) 4984.

    Google Scholar 

  16. DeGrado, W.F., Wassermann, Z.R. and Lear, J.D., Science, 243 (1989) 622.

    Google Scholar 

  17. Hecht, M.H., Richardson, J.S., Richardson, D.C. and Ogden, R.C., Science, 249 (1990) 884.

    Google Scholar 

  18. Regan, L. and DeGrado, W.F., Science, 241 (1988) 976.

    Google Scholar 

  19. Mutter, M., Altmann, E., Altmann, K.-H., Hersperger, R., Koziej, P., Nebel, K. and Tuchscherer, G., Helv. Chim. Acta, 71 (1988) 835.

    Google Scholar 

  20. Tuchscherer, G., Dörner, B., Sila, U., Kamber, B. and Mutter, M., Tetrahedron, 49 (1993) 3559.

    Google Scholar 

  21. Mutter, M. and Tuchscherer, G., Makromol. Chem., Rapid Commun., 9 (1988) 437.

    Google Scholar 

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Nyanguile, O., Mutter, M. & Tuchscherer, G. Synthesis of antiparallel 4α-helix bundle TASP by chemoselective ligation. Lett Pept Sci 1, 9–16 (1994). https://doi.org/10.1007/BF00132757

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  • DOI: https://doi.org/10.1007/BF00132757

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