Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements |
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Authors: | Alicia A Williams Sayo O Fakayode Onur Alptürk Christina M Jones Mark Lowry Robert M Strongin Isiah M Warner |
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Institution: | (1) Department of Chemistry, Louisiana State University, 434 Choppin Hall, Baton Rouge, LA 70803, USA;(2) Department of Chemistry, Winston-Salem State University, Winston-Salem, NC 27110, USA;(3) Department of Chemistry, Portland State University, Portland, OR 97207, USA |
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Abstract: | Novel fluorescent chiral molecular micelles (FCMMs) were synthesized, characterized, and employed as chiral selectors for
enantiomeric recognition of non-fluorescent chiral molecules using steady state fluorescence spectroscopy. The sensitivity
of the fluorescence technique allowed for investigation of low concentrations of chiral selector (3.0 × 10−5 M) and analyte (5.0 × 10−6 M) to be used in these studies. The chiral interactions of glucose, tartaric acid, and serine in the presence of FCMMs poly(sodium
N-undecanoyl-l-tryptophanate) poly-l-SUW], poly(sodium N-undecanoyl-l-tyrosinate) poly-l-SUY], and poly(sodium N-undecanoyl-l-phenylalininate) poly-SUF] were based on diastereomeric complex formation. Poly-l-SUW had a significant fluorescence emission spectral difference as compared to poly-l-SUY and poly-l-SUF for the enantiomeric recognition of glucose, tartaric acid, and serine. Studies with the hydrophobic molecule α-pinene
suggested that poly-l-SUY and poly-l-SUF had better chiral discrimination ability for hydrophobic analytes as compared to hydrophilic analytes. Partial-least-squares
regression modeling (PLS-1) was used to correlate changes in the fluorescence emission spectra of poly-l-SUW due to varying enantiomeric compositions of glucose, tartaric acid, and serine for a set of calibration samples. Validation
of the calibration regression models was determined by use of a set of independently prepared samples of the same concentration
of chiral selector and analyte with varying enantiomeric composition. Prediction ability was evaluated by use of the root-mean-square
percent relative error (RMS%RE) and was found to range from 2.04 to 4.06%.
Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
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Keywords: | Chiral analysis Fluorescence spectroscopy Multivariate regression analysis Molecular micelle |
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