H. Miyazaki et al., OPTICAL RESOLUTION BY PREFERENTIAL CRYSTALLIZATION AND REPLACING CRYSTALLIZATION OF DL-ALLOTHREONINE, Bulletin of the Chemical Society of Japan, 67(7), 1994, pp. 1899-1903
The ternary solubility diagram, X-ray diffraction pattern, and infrare
d spectra have suggested that DL-allothreonine [DL-aThr] exists as a c
onglomerate. The optical resolution by successive preferential crystal
lization gave both D- and L-aThr of 95% optical purities in 9-13% degr
ees of resolution. The successive replacing crystallization was more s
uccessfully achieved by the coexisting 4-hydroxy-L-proline, as an opti
cally active cosolute, in a racemic supersaturated solution. D-aThr of
94% optical purity was allowed to crystallize preferentially without
seeding D-aThr in 24% degree of resolution, whereas L-aThr of 81% opti
cal purity from the mother liquor was allowed to crystallize by seedin
g L-aThr in 22% degree of resolution. Recystallization of the obtained
D- and L-aThr from water gave an optically pure form.