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Calix[4]arene‐Based Enantioselective Fluorescent Sensors for the Recognition of N‐Acetyl‐aspartate
Author(s) -
QING GuangYan,
CHEN ZhiHong,
WANG Feng,
YANG Xi,
MENG LingZhi,
HE YongBing
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890135
Subject(s) - chemistry , fluorescence , fluorophore , enantiomer , hydrogen bond , enantioselective synthesis , receptor , stereochemistry , stoichiometry , ion , medicinal chemistry , molecule , organic chemistry , biochemistry , catalysis , physics , quantum mechanics
Two‐armed chiral anion receptors ( 1 and 2 ), calix[4]arenes bearing dansyl fluorophore and (1 R ,2 R )‐ or (1 S ,2 S )‐1,2‐diphenylethylenediamine binding sites, were prepared and examined for their chiral amino acid anion binding abilities by the fluorescence spectra in dimethylsulfoxide (DMSO). The results of non‐linear curve fitting indicate that 1 or 2 forms a 1:1 stoichiometry complex with N ‐acetyl‐ L ‐ or D ‐aspartate by multiple hydrogen bonding interactions, exhibiting good enantioselective fluorescent recognition for the enantiomers of N ‐acetyl‐aspartate, [receptor 1 : K ass( D ) / K ass( L ) =6.74; receptor 2 : K ass( L ) / K ass( D ) =6.48]. The clear fluorescent response difference indicates that receptors 1 and 2 could be used as a fluorescent chemosensor for N ‐Acetyl‐aspartate.
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