1. From MonoBINOL to BisBINOL: Expanded Enantioselective Fluorescent Recognition of Amino Acids
- Author
-
Bingyi Huo, Lin Pu, Xiao-Qi Yu, Jun Tian, Yalin Wang, Shanshan Yu, Feng Zhao, and Kai Lu
- Subjects
chemistry.chemical_classification ,Molecular Structure ,Base (chemistry) ,010405 organic chemistry ,Organic Chemistry ,Triphenyl phosphonium ,Diastereomer ,Enantioselective synthesis ,Substrate (chemistry) ,Stereoisomerism ,010402 general chemistry ,01 natural sciences ,Fluorescence ,Medicinal chemistry ,0104 chemical sciences ,Amino acid ,chemistry.chemical_compound ,Spectrometry, Fluorescence ,chemistry ,Amines ,Amino Acids ,Methylene - Abstract
Condensation of the methoxymethyl-protected (R)-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 (R,R)-4. 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 (R,R)-4 with l- and d-valine, and the reactions of these imines with Zn(OAc)2 were investigated by various spectroscopic methods for a better understanding of the enantioselective fluorescent recognition process.
- Published
- 2021