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Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

Journal of Fluorescence volume 18, pages 285–296 (2008)Cite this article

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%.

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Acknowledgements

I. M. Warner acknowledges the National Institutes of Health, the National Science Foundation, and the Philip W. West Endowment for support of this research.

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Authors and Affiliations

  1. Department of Chemistry, Louisiana State University, 434 Choppin Hall, Baton Rouge, LA, 70803, USA

    Alicia A. Williams, Onur Alptürk, Christina M. Jones, Mark Lowry & Isiah M. Warner

  2. Department of Chemistry, Winston-Salem State University, Winston-Salem, NC, 27110, USA

    Sayo O. Fakayode

  3. Department of Chemistry, Portland State University, Portland, OR, 97207, USA

    Robert M. Strongin

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  1. Alicia A. Williams
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  2. Sayo O. Fakayode
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  3. Onur Alptürk
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  4. Christina M. Jones
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  5. Mark Lowry
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  6. Robert M. Strongin
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  7. Isiah M. Warner
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Correspondence to Isiah M. Warner.

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Supporting Information Available

1H-NMR and 13C-NMR spectra of undecanoyl-l-tryptophan, undecanoyl-l-tyrosine, and undecanoyl-l-phenylalanine. This material is available free of charge via the Internet at http://pubs.acs.org (PDF 38.1 KB).

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Williams, A.A., Fakayode, S.O., Alptürk, O. et al. Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements. J Fluoresc 18, 285–296 (2008). https://doi.org/10.1007/s10895-007-0268-z

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  • DOI: https://doi.org/10.1007/s10895-007-0268-z

Keywords

  • Chiral analysis
  • Fluorescence spectroscopy
  • Multivariate regression analysis
  • Molecular micelle