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Enantioselective Fluorescent Recognition of Amino Acids in Aqueous Solution by Using a Chiral Aldehyde Probe
Author(s) -
Zhao Feng,
Du Yi,
Tian Jun,
Shi Dan,
Wang Yachen,
Hu Lingling,
Yu Shanshan,
Yu Xiaoqi,
Pu Lin
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701773
Subject(s) - enantioselective synthesis , chemistry , aldehyde , enantiomer , imine , amino acid , fluorescence , aqueous solution , chiral derivatizing agent , combinatorial chemistry , organic chemistry , catalysis , chiral column chromatography , biochemistry , physics , quantum mechanics
A BINOL‐based chiral aldehyde containing hydrophilic PEG groups was synthesized. It was found that in HEPES buffer solution at neutral pH this compound in combination with Zn 2+ ions shows a highly enantioselective fluorescent response toward various amino acids and can be used to determine their enantiomeric composition. The 1 H NMR and mass spectroscopic analyses have shown that the BINOL‐based chiral aldehyde can react with one enantiomer of an amino acid and Zn 2+ to form the corresponding imine‐zinc complex more than the other enantiomer, giving the observed highly enantioselective fluorescence enhancement.