Summary
The oxidation of thioether bonds in peptides is still one of the major side reactions during peptide synthesis and it is easily detected by electrospray mass spectrometry. A fast reduction of oxidized methionine, biotin and tripalmitoyl-S-glyceryl-cysteine in synthetic peptides is possible using mixtures of trimethylsilylbromide and ethanedithiol as additives in trifluoroacetic acid. Simple procedures have been worked out which are especially suitable for handling the reduction of large numbers of peptides, prepared by multiple peptide synthesis, and of peptide libraries.
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References
Bodanszky, M. and Martinez, J., Synthesis, (1981) 333.
Jung, G. and Beck-Sickinger, A.G., Angew. Chem., Int. Ed. Engl., 31 (1992) 367.
Schnorrenberg, G. and Gerhardt, H., Tetrahedron, 45 (1989) 7759.
Norris, K., Halstrom, J. and Brunfeldt, K., Acta Chem. Scand., 25 (1971) 945.
Drabowiecz, J., Numata, T. and Oae, S., Org. Prep. Proced. Int., 9 (1977) 63.
Drabowiecz, J., Togo, H., Mikolajczyk, M. and Oae, S., Org. Prep. Proced. Int., 16 (1984) 171.
Madesclarie, M., Tetrahedron, 44 (1988) 6537.
Grossert, J.S. In Patai, S., Rappoport, Z. and Stirling, C. (Eds.) The Chemistry of Sulphones and Sulphoxides, Wiley, Chichester, 1988, pp. 925–968.
Polzhofer, K.P. and Ney, K.H., Tetrahedron, 27 (1971) 1997.
Houghten, R.A. and Li, V.H., Anal. Biochem., 98 (1979) 3646.
Mapelli, C. and Leftheris, K., In Schneider, C.H. and Eberle, A.N. (Eds.) Peptides 1992 (Proceedings of the Twenty-Second European Peptide Symposium), ESCOM, Leiden, 1992, pp. 207–208.
Beck, W., Benz, I., Jung, G. and Kohlhardt, M., Biochim. Biophys. Acta, (1994) in press.
Obermeier, A., Halfter, H., Wiesmüller, K.-H., Jung, G., Schlessinger, J. and Ullrich, A., EMBO J., 12 (1993) 933.
Kitas, E.A., Perich, J.W., Tregear, G.W. and Johns, R.B., J. Org. Chem., 55 (1990) 4181.
Olah, G.A., Husain, A., Singh, B.P. and Mehrotra, A.K., J. Org. Chem., 48 (1983) 3667.
Olah, G.A., Gupta, B.G. and Narang, S.C., Synthesis, (1977) 583.
Numata, T., Togo, G. and Oae, S., Chem. Lett., (1979) 329.
Yaijma, H., Fujii, N., Funakoshi, S., Watanabe, T., Murayama, E. and Otaka, A., Tetrahedron, 44 (1988) 805.
Wiesmüller, K.-H., Ph.D. Thesis, University of Tübingen, Tübingen, 1991.
Metzger, J.W., Beck, W. and Jung, G., Angew. Chem., 104 (1992) 235.
Metzger, J.W., Beck, W. and Jung, G., Angew. Chem., Int. Ed. Engl., 31 (1992) 226.
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Beck, W., Jung, G. Convenient reduction of S-oxides in synthetic peptides, lipopeptides and peptide libraries. Lett Pept Sci 1, 31–37 (1994). https://doi.org/10.1007/BF00132760
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DOI: https://doi.org/10.1007/BF00132760