Summary
Nitrogen indole protection of the β-methyltryptophan side-chain residue is important for avoiding undesired side reactions during peptide synthesis. Of great importance is the choice of a side-chain protecting group for orthogonal peptide synthesis and its stability under a variety of chemical conditions required for synthesis of the four isomers of this unusual amino acid. We report here the successful use of the mesitylenesulfonyl (Mts) protecting group for β-methyltryptophan in the synthesis of melanotropin and CCK peptide analogues and the ready cleavage of this protecting group under HF conditions.
Similar content being viewed by others
References
Boteju, L.W., Wegner, K. and Hruby, V.J., Tetrahedron Lett., 33 (1992) 7491.
Boteju, L.W., Wegner, K., Qian, X. and Hruby, V.J., Tetrahedron, 50 (1994) 2391.
Fujii, N., Futaki, S., Yasumura, K. and Yajima, H., Chem. Pharm. Bull., 32 (1984) 2660.
Stewart, J.M. and Young, J.D., Solid Phase Peptide Synthesis, 2nd ed., Pierce Chemical Co., Rockford, IL, 1984.
Al-Obeidi, F., Castrucci, A.M., Hadley, M.E. and Hruby, V.J., J. Med. Chem., 32 (1989) 2555.
Castro, B., Dormoy, J.R., Evin, G. and Seive, C., Tetrahedron Lett., 14 (1975) 1219.
Hruby, V.J., Al-Obeide, F., Sanderson, D.G. and Smith, D.D., In Epton, R. (Ed.) Innovations and Perspectives in Solid Phase Synthesis, SPCC (UK) Ltd., Oxford, 1989, pp. 197–203.
Kaiser, E., Colescott, R.L., Bossinger, C.D. and Cook, P.I., Anal. Biochem., 34 (1970) 595.
Alakhov, Y.B., Kiryushkin, A.A., Lipkin, V.M. and Milne, G.W.A., J. Chem. Soc., Chem. Commun., (1970) 406.
Wünsch, E., Jaeger, E., Kisfaludy, L. and Löw, M., Angew. Chem., 89 (1977) 330.
Wünsch, E., Jaeger, E., Deffner, M. and Scharf, R.Z., Physiol. Chem., 353 (1972) 1716.
Jaeger, E., Thamm, P., Knof, S., Wünsch, E., Löw, M. and Kisfaludy, L.Z., Physiol. Chem., 359 (1978) 1617.
Omori, Y., Matsuda, Y., Aimoto, S., Shimonishi, Y. and Yamamoto, M., Chem. Lett., (1976) 805.
Hashizume, K. and Shimonishi, Y., Bull. Chem. Soc. Jpn., 54 (1981) 3806.
Bodanszky, M. and Bodanszky, A., The Practice of Peptide Synthesis, Springer, Berlin, 1984.
Tam, J.P. and Merrifield, R.B., In Undenfriend, S. and Meienhofer, J. (Eds.) The Peptides, Vol. 9, Academic Press, New York, NY, 1987, pp. 185–248.
Yajima, H., Fujii, N., Funakoshi, S., Watanabe, T., Murayama, E. and Otaka, A., Tetrahedron, 44 (1988) 805.
White, P., In Smith, J.A. and Rivier, J.E. (Eds.) Peptides: Chemistry and Biology (Proceedings of the 12th American Peptide Symposium), ESCOM, Leiden, 1992, pp. 537–541.
Tam, J.P., Heath, W.F. and Merrifield, R.B., J. Am. Chem. Soc., 105 (1983) 6443.
Irie, H., Fujii, N., Ogawa, H. and Yajima, H., J. Chem. Soc., Chem. Commun., (1967) 922.
Yajima, H., Kanaki, J., Kitajima, M. and Funakoshi, S., Chem. Pharm. Bull., 28 (1980) 1214.
Kiso, Y., Ukawa, K. and Akita, T., J. Chem. Soc., Chem. Commun., (1980) 101.
Kiso, Y., Ukawa, K., Nakamura, S., Ito, K. and Akita, T., Chem. Pharm. Bull., 28 (1980) 673.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Haskell-Luevano, C., Boteju, L.W. & Hruby, V.J. Facile removal of the N-indole-mesitylenesulfonyl protecting group using HF cleavage conditions. Lett Pept Sci 1, 163–170 (1995). https://doi.org/10.1007/BF00117952
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00117952