A BINOL-based perfluoroalkyl ketone shows a highly enantioselective fluorescence enhancement in the presence of various amino acid-TBA salts and can be used to determine the enantiomeric composition of these compounds. It was found that the amino acid-TBA salts can act as nucleophiles to cleave the perfluoroalkyl group off of the ketones to form the corresponding amides at room temperature in DMSO. This is the first example of an enantioselective fluorescent sensor for the recognition of amino acids by forming amide bonds under very mild conditions. This study has also revealed an unusual concentration effect leading to an “off-on-off” fluorescence response of the sensor toward one enantiomer of the amino acids.

中文翻译：

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通过酰胺形成氨基酸的对映体选择性荧光识别：异常的浓度效应

在各种氨基酸-TBA盐存在下，基于BINOL的全氟烷基酮显示出高度的对映选择性荧光增强，可用于确定这些化合物的对映体组成。已经发现，氨基酸-TBA盐可以充当亲核试剂，以在DMSO中在室温下将全氟烷基从酮上裂解形成相应的酰胺。这是对映选择性荧光传感器的第一个示例，该传感器通过在非常温和的条件下形成酰胺键来识别氨基酸。这项研究还揭示了一种异常的浓度效应，该效应导致传感器对氨基酸的一种对映异构体产生“开-关-关”的荧光响应。