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A versatile chiral selector for determination of enantiomeric composition of fluorescent and nonfluorescent chiral molecules using steady‐state fluorescence spectroscopy
Author(s) -
Williams Alicia A.,
Fakayode Sayo O.,
Lowry Mark,
Warner Isiah M.
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20580
Subject(s) - chemistry , enantiomer , chirality (physics) , fluorescence , analyte , fluorescence spectroscopy , molecule , diastereomer , methanol , micelle , analytical chemistry (journal) , chromatography , organic chemistry , aqueous solution , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A fluorescent chiral molecular micelle (FCMM), poly (sodium N ‐undecanoyl‐ L ‐phenylalaninate) (poly‐ L ‐SUF), was developed as a chiral selector for enantiomeric recognition and determination of enantiomeric composition of four fluorescent and four nonfluorescent chiral molecules by use of steady‐state fluorescence spectroscopy. The influence of FCMM concentration, buffer pH and complexation medium on FCMM‐analyte host–guest complexation, and the emission spectral properties of the resulting complexes were investigated. The chiral interactions of the analytes,1,1′‐binaphthyl‐2,2′‐diamine, 1‐(9‐anthryl)‐2,2,2‐trifluoroethanol, propranolol, naproxen, chloromethyl menthyl ether (CME), citramalic acid, tartaric acid, and limonene (LIM), in the presence of poly‐ L ‐SUF were based on diastereomeric complex formation. The figures of merit obtained from the partial‐least‐squares regression modeling of the calibration samples suggested good prediction ability for the validation of six of the eight chiral analytes. Better host–guest complexation of the more hydrophobic molecules, CME and LIM, were obtained in methanol/water mixtures, resulting in better predictability of the regression models. Prediction ability of the models was evaluated by use of the root‐mean‐square percent relative error ( RMS%RE ) and was found to range from 1.77 to 15.80% (buffer), 1.26 to 7.95% (25:75 methanol/water), and 1.21 to 4.28% (75:25 methanol/water). Chirality, 2009. © 2008 Wiley‐Liss, Inc.