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Resolution of DL-Glutamic Acid with Optically Active Neutral Amino Acid Amides

1962; Oxford University Press; Volume: 26; Issue: 8 Linguagem: Inglês

10.1080/00021369.1962.10858002

1881-1280

Tetsuya Kato, Yoshio Tsuchiya,

Carbohydrate Chemistry and Synthesis

DL-Glutamic acid has been resolved into optically active forms as the diastereoisomeric salt of optically active neutral amino acid amides, and the salt is easily converted to the sodium salt of the active forms. By resolution with L-tyrosinamide and L-leucinamide, sodium L-glutamate was obtained in 65 and 80 per cent yield respectively. Attempts to extend this method to resolution of DL-glutamic acid using L-phenylalaninamide as resolving agent resulted in poor yield of less pure D-glutamic acid. By the infrared spectroscopy and X-ray diffraction analysis it has been confirmed that the diastereoisomeric salts of L-leucinamide or L-tyrosinamide with L- or D-glutamic acid compose a combined salt structure in solid state, whereas L-phenylalaninamide with L- or D-glutamic acid does not compose a characteristic diastereoisomeric salt but rather the mechanical mixture of L-phenylalaninamide and L- or D-glutamate anion in solid state. In the previous study1), it was reported that L-leucinamide forms the characteristic diastereoisomeric salts with racemic N-acyl mono amino acids, most of which are fairly resolved into their antipodes.