Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Resolution of Amino Acids. VIII. The Preparation of the Four Optical Isomers of β-Hydroxyaspartic Acid
Hideo OkaiNaokazu ImamuraNobuo Izumiya
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1967 Volume 40 Issue 9 Pages 2154-2159


The ammonolysis of cis-epoxy succinic acid yielded threo-hydroxy-DL-aspartic acid exclusively, but that of trans-epoxy acid produced a mixture of 68% erythro- and 32% threo-hydroxyaspartic acid. This mixture was separated into the two pure diastereomers through either a Dowex 1 column chromatography or fractional crystallization after the mixture had been changed to ammonium salt. The threo- and erythro-DL-amino acids so prepared were resolved by optically active lysine and ornithine respectively. The contribution (partial molar rotation) of the α-and β-asymmetric centers to the observed molar rotations of the optically active diastereomeric hydroxyaspartic acids in water and 5 N hydrochloric acid was calculated.

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