Semiquantitative Visual Chiral Assay with a Pseudoenantiomeric Fluorescent Sensor Pair
Semiquantitative Visual Chiral Assay with a Pseudoenantiomeric Fluorescent Sensor Pair
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DOI：
10.1021/acs.joc.1c00875
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发表时间：
2021-06-24
影响因子：
3.6
通讯作者：
Pu, Lin
中科院分区：
文献类型：
--
作者：
Chen, Yu;Zhao, Feng;Pu, Lin
合成了一种新的红光荧光探针(R)-5。在Zn2+存在下，该化合物在水溶液中与多种氨基酸处理后，在λ = 655 nm处表现出良好的对映选择性荧光增强。该探针与在λ = 505 nm处具有对映选择性荧光增强的绿色发光探针(S)-4结合，由于它们的对映选择性相反，形成了假对映体传感器对。该传感器对可以在两个不同波长（δ = 150 nm）同时检测手性氨基酸的两个对映体。它被用来直观和半定量地测定氨基酸的对映体组成。例如，当(R)-5和(S)-4的1:1混合物用Zn(OAc)(2)和0-100% [D-His]的组氨酸样品处理时，在365 nm的紫外灯下，混合物的颜色从绿色变为黄色、橙色和红色，从而可以快速定量[D-His]%。这是第一个使用荧光可视化量化手性化合物对映体组成的例子。
A new red-light-emitting fluorescent probe (R)-5 was synthesized. In the presence of Zn2+, this compound was found to exhibit good enantioselective fluorescence enhancement at lambda = 655 nm when treated with a variety of amino acids in aqueous solution. This probe in combination with a green-light-emitting probe (S)-4 that has enantioselective fluorescence enhancement at lambda = 505 nm has formed a pseudoenantiomeric sensor pair because of their opposite enantioselectivities. This sensor pair can simultaneously detect both enantiomers of a chiral amino acid at two very different wavelengths (Delta = 150 nm). It was used to visually and semiquantitatively determine the enantiomeric compositions of amino acids. For example, when a 1:1 mixture of (R)-5 and (S)-4 was treated with Zn(OAc)(2) and histidine samples of 0-100% [D-His], the color of the mixtures changed from green to yellow, orange, and red under a UV lamp (365 nm), which allowed a quick quantification of [D-His]%. This is the first example of using fluorescence to visually quantify the enantiomeric composition of chiral compounds.