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Enantioselective Fluorescent Sensor Based on Calix[4]arene and S ‐Binol for the Recognition of N ‐Boc‐glutamate
Author(s) -
HU Chenguang,
HUANG Xiaohuan,
CHEN Zhihong,
HE Yongbing
Publication year - 2009
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.200990009
Subject(s) - chemistry , fluorescence , enantioselective synthesis , enantiomer , hydrogen bond , proton nmr , glutamate receptor , stoichiometry , molecular recognition , stereochemistry , combinatorial chemistry , receptor , organic chemistry , catalysis , molecule , biochemistry , physics , quantum mechanics
A new chiral macrocyclic receptor 4 based on calix[4]arene and S ‐binol units was synthesized. The binding properties for anions were examined by fluorescence and 1 H NMR spectra. The results of non‐linear curve fitting indicated that the receptor 4 formed a 1:1 stoichiometry complex with N ‐Boc‐ L ‐ or D ‐glutamate by multiple hydrogen bonding interactions, exhibiting a good enantioselective fluorescent recognition for the enantiomers of N ‐Boc‐glutamate. The enantioselectivity: K ass( L ) / K ass( D ) =4.65. The different fluorescent response indicates that the receptor 4 could be used as a fluorescent chemosensor for N ‐Boc‐glutamate.