Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, United States.
J Org Chem. 2020 Apr 3;85(7):4901-4905. doi: 10.1021/acs.joc.0c00064. Epub 2020 Mar 25.
The addition of Mg is found to turn on the fluorescence response of a molecular probe, 3,3'-diformyl-1,1'-bi-2-naphthol, toward chiral amino acids with high enantioselectivity. It is further found that the enantioselective fluorescence responses of the molecular probe in the presence of Mg toward certain amino acids are the opposite of those in the presence of Zn, that is, using Mg with an l-amino acid generates much greater fluorescence enhancement than with the corresponding d-amino acid, but using Zn with the d-amino acid gives much greater fluorescence than with the l-enantiomer. Thus, simply changing the metal cation additive allows the chirality sense of the fluorescence-based molecular recognition to be easily regulated.
添加镁被发现可以开启分子探针 3,3'-二醛基-1,1'-联萘酚对手性氨基酸的荧光响应，具有高对映选择性。进一步发现，分子探针在镁存在下对某些氨基酸的对映选择性荧光响应与锌存在下的情况相反，即在存在镁的情况下，l-氨基酸的分子探针的荧光增强程度远大于相应的 d-氨基酸，但在存在锌的情况下，d-氨基酸的荧光增强程度远大于 l-对映体。因此，只需改变金属阳离子添加剂，就可以轻松调节基于荧光的分子识别的手性感知。
