通过形成酰胺对氨基酸进行对映选择性荧光识别：一种不寻常的浓度效应。
Enantioselective Fluorescent Recognition of Amino Acids by Amide Formation: An Unusual Concentration Effect.
机构信息
Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319 United States.
Key Laboratory of Cluster Science of Ministry of Education, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology , 5 Zhongguancun Road, Beijing 100081, P. R. China.
出版信息
J Org Chem. 2017 Dec 1;82(23):12669-12673. doi: 10.1021/acs.joc.7b02456. Epub 2017 Nov 15.
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.
一种基于联二萘酚的全氟烷基酮在存在各种氨基酸-TBA 盐的情况下表现出高度对映选择性的荧光增强，可用于测定这些化合物的对映体组成。研究发现，氨基酸-TBA 盐可以作为亲核试剂，在室温下在 DMSO 中切断酮上的全氟烷基，形成相应的酰胺。这是首例在非常温和的条件下通过形成酰胺键来识别氨基酸的对映选择性荧光传感器。该研究还揭示了一种不寻常的浓度效应，导致传感器对一种氨基酸对映体的荧光响应呈现“关-开-关”。
Zotero 插件