Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 50, Issue 2, Pages 287-291Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.50.287
Keywords
allothroonine; optical resolution; alanine; threonine; epimerization
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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 alpha-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.
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