Klussmann Martin, Izumi Toshiko, White Andrew J P, Armstrong Alan, Blackmond Donna G
Department of Chemistry, Imperial College London, London SW7 2AZ, U.K.
J Am Chem Soc. 2007 Jun 20;129(24):7657-60. doi: 10.1021/ja0708870. Epub 2007 May 26.
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.
同手性从益生元环境中的演化长期以来一直吸引着科学家。在此，我们报告了如何通过操纵氨基酸的相行为来制备高度对映体富集的溶液，这一概念对益生元化学具有深远影响。我们证明，L型和D型氨基酸的水性混合物的低共熔组成可通过添加与手性氨基酸共结晶的非手性二羧酸来调节。我们发现，在几种情况下，这些体系会产生对映体过量（ee）为98%或更高的新低共熔组成。这项工作表明了现代晶体工程的一个先驱，它为同手性的演化提供了一种通用且简便的机制，同时也为形成外消旋化合物的分子对映体的分离带来了概念上的进展。
