Summary
Polymer-bound N-tritylhydrazines 4 were easily prepared by reacting polymeric tritylchlorides 3 with hydrazine. Subsequently, compounds 4 have been successfully applied to the solid phase synthesis of partially protected peptide hydrazides using 1-hydroxybenzotriazolyl esters of Fmoc- or Trt-amino acids. The synthesized peptide hydrazides can be quantitatively split off from the resins by mild acidic treatment, while the benzyl- and tert-butyl protecting groups remain unaffected.
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References
Honzl, J. and Rudinger, J., Coll. Czech. Chem. Commun., 26 (1961) 2333.
Hofmann, K., Haas, W., Smithers, M.J., Wells, R.D., Wolman, Y., Yanaihara, N. and Zanetti, G., J. Am. Chem. Soc., 87 (1965) 620.
For a review see: Meienhofer, J., THe Azide Method in Peptide Synthesis, The Peptides, Vol. 1, Academic Press, New York, NY, 1979, pp. 197–239.
Barlos, K., Gatos, D., Kallitsis, J., Papaphotiu, G., Sotiriou, P., Wenqing, Y. and Schäfer, W., Tetrahedron Lett., 30 (1989) 3943.
Barlos, K., Gatos, D., Kapolos, S., Papaphotiu, G., Schäfer, W. and Wenqing, Y., Tetrahedron Lett., 30 (1989) 3947.
Rink, H., Tetrahedron Lett., 28 (1987) 3787.
Barlos, K., Gatos, D., Hondrelis, J., Matsoukas, J., Moore, G.J., Schäfer, W. and Sotiriou, P., Liebigs Ann. Chem., (1989) 951.
Mergler, M., Tanner, R., Gostellil, J. and Grogg, P., Tetrahedron Lett., 29 (1988) 4005.
Barlos, K., Gatos, D. Koutsogianni, S., Schäfer, W., Stavropoulos, G. and Wenqing, Y., Tetrahedron Lett., 32 (1991) 471.
Barlos, K., Chatzi, O., Gatos, D. and Stavropoulos, G., Int. J. Pept. Protein Res., 37 (1991) 513.
Wang, S.S. J. Am. Chem. Soc., 95 (1973) 1328.
Wang, S.S. and Merrifield, R.B., J. Am. Chem. Soc., 91 (1969) 6488.
Van Vliet, A., Rijkers, D.T.S. and Tesser, G.I., In Maia, H.L.S. (Ed.) Peptides 1994 (Proceedings of the 23rd European Peptide Symposuim), ESCOM, Leiden, 1995, p. 153.
Weygand, F. and Steglich, W., Chem. Ber., 92 (1959) 313.
Barlos, K., Gatos, D., Kallitsis, J., Papaioannou, D. and Sotiriou, P., Liebigs Ann. Chem., (1989) 1079.
Barlos, K., Gatos, D., Kallitsis, J., Papaioannou, D. Sotiriou, P., and Schäfer, W., Liebigs Ann. Chem., (1987) 1031.
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Stavropoulos, G., Gatos, D., Magafa, V. et al. Preparation of polymer-bound trityl-hydrazines and their application in the solid phase synthesis of partially protected peptide hydrazides. Lett Pept Sci 2, 315–318 (1996). https://doi.org/10.1007/BF00142245
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DOI: https://doi.org/10.1007/BF00142245