基于呋喃并联萘酚的冠醚作为对苯乙胺和缬氨酸乙酯进行对映选择性识别的荧光手性传感器。
Furo-fused BINOL based crown as a fluorescent chiral sensor for enantioselective recognition of phenylethylamine and ethyl ester of valine.
作者信息
Upadhyay Sunil P, Pissurlenkar Raghuvir R S, Coutinho Evans C, Karnik Anil V
机构信息
Department of Chemistry, University of Mumbai, Vidyanagari, Kalina, Santacruz (East), Mumbai 400 098, India.
出版信息
J Org Chem. 2007 Jul 20;72(15):5709-14. doi: 10.1021/jo070850y. Epub 2007 Jun 20.
A furo-fused BINOL based chiral crown was developed as an enantioselective chiral sensor for phenylethylamine and ethyl ester of valine. Fusion of furan to BINOL has resulted in a highly stereo-discriminating backbone for the chiral crown developed. This chiral crown exhibited a fluorescence enhancement difference of 2.97 times between two enantiomers of phenylethylamine and 2.55 times between two enantiomers of ethyl ester of valine. The ratio of association constants for two diastereomeric complexes of two enantiomers of phenylethylamine was found to be 11.30, and the ratio for two enantiomers of ethyl ester of valine was 7.02.
一种基于呋喃稠合联萘酚的手性冠醚被开发用作苯乙胺和缬氨酸乙酯的对映选择性手性传感器。呋喃与联萘酚的稠合为所开发的手性冠醚产生了一个高度立体区分的主链。这种手性冠醚在苯乙胺的两种对映体之间表现出2.97倍的荧光增强差异，在缬氨酸乙酯的两种对映体之间表现出2.55倍的荧光增强差异。发现苯乙胺两种对映体的两种非对映体配合物的缔合常数之比为11.30，缬氨酸乙酯两种对映体的缔合常数之比为7.02。
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