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

Authors

Alicia A. Williams, Louisiana State University
Sayo O. Fakayode, Winston-Salem State University
Onur Alptürk, Louisiana State UniversityFollow
Christina M. Jones, Louisiana State University
Mark Lowry, Louisiana State UniversityFollow
Robert M. Strongin, Portland State UniversityFollow
Isiah M. Warner, Louisiana State UniversityFollow

Document Type

Post-Print

Publication Date

3-2008

Subjects

Fluorescence spectroscopy, Multivariate analysis, Hydrophobic surfaces, Fluorescence

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 x 10(-5) M) and analyte (5.0 x 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 alpha-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%.

Description

This is an Author's Original Manuscript of an article whose final and definitive form, the Version of Record, has been published in the Journal of Fluorescence, March 2008. Copyright Taylor & Francis, available online at: http://link.springer.com/article/10.1007%2Fs10895-007-0268-z

DOI

10.1007/s10895-007-0268-z

Persistent Identifier

http://archives.pdx.edu/ds/psu/11136

Citation Details

Williams, Alicia A.; Fakayode, Sayo O.; Alptürk, Onur; Jones, Christina M.; Lowry, Mark; Strongin, Robert M.; and Warner, Isiah M., "Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements" (2008). Chemistry Faculty Publications and Presentations. 60.
http://archives.pdx.edu/ds/psu/11136