Emergence of Solution-Phase Homochirality via Crystal Engineering of Amino Acids

The evolution of homochirality from a prebiotic environment has long intrigued scientists.
Here we report how highly enantioenriched solutions may be produced by manipulation of amino acid
phase behavior, a concept that has far-reaching implications for prebiotic chemistry. We demonstrate
that the eutectic composition of aqueous mixtures of l and d amino acids may be tuned by the addition of
achiral dicarboxylic acids that cocrystallize with chiral amino acids. We find that, in several cases,
these systems yield new eutectic compositions of 98% ee or higher. This work suggests a forerunner
of modern crystal engineering that provides a general and facile mechanism for the evolution of
homochirality as well as a conceptual advance for the separation of enantiomers of molecules forming
racemic compounds.