Preparation of Optically Active Allothreonine via Optical Resolution by Replacing Crystallization

概要

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An attempt was made to use a simple procedure to obtain D-and L-allothreonine(D-and L-aThr), which are non-proteinogenic α-amino acids and are useful as chiral reagents in asymmetric syntheses. DL-aThr that exists as a conglomerate was optically resolved by replacing crystallization with L-alanine(L-Ala)as an optically active co-solute. D-aThr was preferentially crystallized from an aqueous solution of DL-aThr in the presence of L-Ala, as was L-aThr in the presence of D-Ala. Furthermore, a diasteroisomeric mixture of D-aThr and L-threonine(L-Thr)and one of L-aThr and D-Thr were prepared, respectively, by epimerization of L-and D-Thr using salicylaldehyde as the catalyst in acetic acid. Based on the result of the replacing crystallization, D-and L-aThr were separated from aqueous solutions of the diastereoisomeric mixtures in the presence of L-and D-Ala. The partially resolved D-and L-aThr were recrystallized from water to yield the corresponding enantiomers in optically pure forms.
公益社団法人日本薬学会の論文
2002-02-01