Abstract
THE o-nitrophenylsulphenyl (NPS) residue has recently been introduced as an amine-protecting group for amino-acids and peptides during peptide synthesis by Zervas et al.1. It is readily cleaved by mild acidolysis using 2–3 equivalents of hydrochloric acid in ether. Although this treatment allows the selective cleavage of the o-nitrophenylsulphenamide group in the presence of acid-labile tert-butylesters in the peptide moiety under carefully controlled conditions2 another cleavage procedure avoiding the use of acid altogether might prove useful.
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References
Zervas, L., Borovas, D., and Gazis, E., J. Amer. Chem. Soc., 85, 3660 (1963).
Zervas, L., Photaki, I., Poduska, K., and Sheppard, B. C., Proc. Seventh European Peptide Symp., Budapest, 1964, Acta Chim. Acad. Sci. Hung. (in the press).
For reviews compare Pettit, G. R., and Van Tamelen, E. E., in Org. Reactions, 12, 356 (1962). Hauptmann, H., and Walther, W. F., Chem. Rev., 62, 347 (1962).
McKay, F. C., and Albertson, N. F., J. Amer. Chem. Soc., 79, 4686 (1957); Anderson, G. W., and McGregor, A. C., 79, 6180 (1957).
Roeske, R., Chem. and Indust., 1121 (1959). Anderson, G. W., and Callahan, F. M., J. Amer. Chem. Soc., 82, 3359 (1960).
Beyerman, H. C., and Bontekoe, J. S., Proc. Chem. Soc., 249 (1961); Rec. Trav. Chim. Pays-Bas, 81, 691, 699 (1962). Schröder, E., Liebigs Ann. Chem., 670, 127 (1963). Callahan, F. M., Anderson, G. W., Paul, R., and Zimmerman, J. A., J. Amer. Chem. Soc., 85, 201 (1963).
Dane, E., Drees, F., Konrad, P., and Dockner, T., Angew. Chem., 74, 873 (1962).
Anderson, G. W., Zimmerman, J. E., and Callahan, F. M., J. Amer. Chem. Soc., 85, 3039 (1963); 86, 1839 (1964).
Anderer, F. A., et al., Nature, 186, 922 (1960); Z. Naturforschg., 17, b, 536 (1962). Tsugita, A., et al., Proc. U. S. Nat. Acad. Sci., 46, 1463 (1960).
Prepared according to Billica, H. R., and Adkins, H., Organic Syntheses Coll., 3, 176 (1955).
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MEIENHOFER, J. Cleavage of o-Nitrophenylsulphenamides by Raney Nickel and Applications for Peptide Synthesis. Nature 205, 73–75 (1965). https://doi.org/10.1038/205073b0
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DOI: https://doi.org/10.1038/205073b0
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