Potential carcinostatics. Synthesis and biological properties of d- and l-.beta.,.beta.-difluoroaspartic acid and .beta.,.beta.-difluoroasparagine

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Abstract
Di-tert-butyl .beta.,.beta.-difluorooxaloacetate, prepared by fluorination of di-tert-butyl oxaloacetate with perchloryl fluoride, was converted to di-tert-butyl .beta.,.beta.-difluoroaspartate via its O-methyl oxime, followed by reduction. The tert-butyl ester was hydrolyzed to give a mixture of dl-.beta.,.beta.-difluoroaspartic acid, which was resolved via its brucine salts. dl-Difluoroaspartic acid was converted into .beta.,.beta.-difluoroasparagine by monoesterification and subsequent ammonolysis. Racemic .beta.,.beta.-difluoroaspartic acid inhibits aspartate aminotransferase. Cell growth of 3T3-F [mouse fibroblast] cells was slightly inhibited by l-.beta.,.beta.-difluoroaspartic acid while the d enantiomer was without effect in this test system.

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