Abstract
IN 1947, Ehrensvärd suggested the use of a new protective group for peptide synthesis1. According to his investigations, the phenylthiocarbonyl grouping (C6H5—S—C—O—) can be used advantageously for the protection of the amino-groups of amino-acids. The phenylthiocarbonyl-group could be split off from the N-phonylthiocarbonyl -peptide derivatives by means of lead acetate. Lindenmann, Khan and Hofmann2 confirmed Ehrensvard's observations ; but according to their investigations hydantoins, not peptides, resulted under the influence of lead acetate. As no method was given for splitting off the phenylthiocarbonyl-group, we attempted the application of oxidative methods, and with complete success. The oxidation is carried out with 2.5 moles of perbenzoic acid at − 5° in acetic acid – benzene, benzene – tetra hydrofurane, dioxane or dioxane containing preferably 2 per cent of water. The products of oxidation probably represent a type of mixed anhydrides of carbamic acids with sulphinic acids hitherto unknown:
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References
Ehrensvärd, G. C. H., Nature, 159, 500 (1947).
Lindenmann, A., Khan, N. H., and Hofmann, K., J. Amer. Chem. Soc., 74, 476 (1952).
Schuller, W. H., and Niemann, C., J. Amer. Chem. Soc., 75, 3425 (1953). Crosby, D. G., and Niemann, C., J. Amer. Chem. Soc., 76, 4458 (1954).
Arndt, F., Milde, E., and Eckert, G., Ber., 56, 1983 (1923).
Sheehan, J. C., and Hess, G. P., J. Amer. Chem. Soc., 77, 139 (1955).
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KOLLONITSCH, J., GÁBOR, V. & HAJÓS, A. New Methods for the Synthesis of Peptides. Nature 177, 841–842 (1956). https://doi.org/10.1038/177841a0
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DOI: https://doi.org/10.1038/177841a0
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