Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Department of Chemistry, University of Virginia, McCormick Road, Charlottesville, Virginia 22904, United States.
J Org Chem. 2021 May 7;86(9):6780-6786. doi: 10.1021/acs.joc.1c00507. Epub 2021 Apr 26.
Condensation of the methoxymethyl-protected ()-3,3'-diformyl-1,1'-bi-2-naphthol (BINOL) with (pyridine-2,6-diylbis(methylene))bis(triphenyl phosphonium)dibromide in the presence of a base followed by deprotection gave a new bisBINOL-based fluorescent probe (,)-. This compound showed expanded substrate scope in the recognition of amino acids with good enantioselective fluorescence responses toward 17 common amino acids. Two diastereomeric imines were synthesized from the condensation of (,)- with l- and d-valine, and the reactions of these imines with Zn(OAc) were investigated by various spectroscopic methods for a better understanding of the enantioselective fluorescent recognition process.
将（）-3,3'-二醛基-1,1'-联萘二醇（BINOL）的甲氧基甲基保护物与（吡啶-2,6-二基双亚甲基）双（三苯基膦）二溴化物在碱存在下缩合，然后脱保护，得到一种新的基于双 BINOL 的荧光探针（，）-。该化合物在识别氨基酸方面表现出扩展的底物范围，对 17 种常见氨基酸具有良好的对映选择性荧光响应。通过各种光谱方法研究了（，）-与 L-和 D-缬氨酸缩合得到的两个非对映异构体亚胺与 Zn(OAc)的反应，以更好地理解对映选择性荧光识别过程。
