Abstract
AN exception to the general applicability of the method devised by du Vigneaud and Meyer1 for the racemization of N-acyl-α-amino-acids has been discovered in the course of an attempt to racemize N-acetyl- and N-benzoyl-L-aspartic acids. The method of du Vigneaud and Meyer depends for its success upon the intermediate formation of a readily racemizable oxazolone when an aqueous solution of the sodium salt of such an acid is stirred with acetic anhydride. This treatment, which leads to the complete racemization of the N-acetyl derivatives of optically active methionine, cystine, arginine, tyrosine, phenylalanine, tryptophane and glutamic acid1,2, achieves, however, only 13 per cent and 24 per cent racemization when applied to N-acetyl- and N-benzoyl-L-aspartic acids respectively.
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References
du Vigneaud, V., and Meyer, C. E., J. Biol. Chem., 98, 295 (1932).
du Vigneaud, V., and Sealock, R. R., J. Biol. Chem., 96, 511 (1932).
Baker, W., and Ollis, W. D., J. Chem. Soc., 345 (1949).
Harington, C. R., and Overhoff, J., Biochem. J., 27, 338 (1933).
Carter, H. E., and Stevens, C. M., J. Biol. Chem., 133, 117 (1940).
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BARKER, C. Racemization of N-Acylaspartic Acids. Nature 168, 908–909 (1951). https://doi.org/10.1038/168908a0
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DOI: https://doi.org/10.1038/168908a0
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