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

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• 作者：Martin Klussmann ; Toshiko Izumi ; Andrew J. P. White ; Alan Armstrong ; Donna G. Blackmond
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：June 20, 2007
• 年：2007
• 卷：129
• 期：24
• 页码：7657 - 7660
• 全文大小：225K
• 年卷期：v.129,no.24(June 20, 2007)
• ISSN：1520-5126

文摘

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 acidphase behavior, a concept that has far-reaching implications for prebiotic chemistry. We demonstratethat the eutectic composition of aqueous mixtures of L and D amino acids may be tuned by the addition ofachiral 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 forerunnerof modern crystal engineering that provides a general and facile mechanism for the evolution ofhomochirality as well as a conceptual advance for the separation of enantiomers of molecules formingracemic compounds.