Department of Chemistry , University of Virginia , Charlottesville , Virginia 22904 , United States.
J Am Chem Soc. 2019 Jan 9;141(1):175-181. doi: 10.1021/jacs.8b07803. Epub 2018 Dec 26.
A novel fluorescent probe based on a bisbinaphthyl structure has been designed and synthesized. This compound in combination with Zn(II) has exhibited highly enantioselective fluorescence enhancement with 13 common free amino acids. For example, its enantiomeric fluorescent enhancement ratios ( ef or Δ I/Δ I) in the presence of the following amino acids are extremely high: 177 for valine, 199 for methionine, 186 for phenylalanine, 118 for leucine, and 89 for alanine. The observed high enantioselectivity and the extent of the substrate scope are unprecedented in the fluorescent recognition of free amino acids. This fluorescent probe can be applied to determine the enantiomeric composition of the structurally diverse chiral amino acids. NMR and mass spectroscopic investigations have provided clues to elucidate the observed high enantioselectivity.
一种基于双萘并[2,1- b : 2 ',1 '- f ]噻吩结构的新型荧光探针已被设计和合成。该化合物与 Zn(II) 结合，对 13 种常见的游离氨基酸表现出高度的对映选择性荧光增强。例如，其在以下氨基酸存在时的对映体荧光增强比（ ef 或 Δ I/Δ I）非常高：缬氨酸为 177，蛋氨酸为 199，苯丙氨酸为 186，亮氨酸为 118，丙氨酸为 89。在游离氨基酸的荧光识别中，观察到的高对映选择性和底物范围是前所未有的。这种荧光探针可用于测定结构多样的手性氨基酸的对映体组成。NMR 和质谱研究为阐明观察到的高对映选择性提供了线索。
