Racemization of N-Acylaspartic Acids

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

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    du Vigneaud, V., and Meyer, C. E., J. Biol. Chem., 98, 295 (1932).

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    du Vigneaud, V., and Sealock, R. R., J. Biol. Chem., 96, 511 (1932).

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    Baker, W., and Ollis, W. D., J. Chem. Soc., 345 (1949).

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    Harington, C. R., and Overhoff, J., Biochem. J., 27, 338 (1933).

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    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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