Title page for ETD etd-11142007-183128

Type of Document Master's Thesis
Author Richard, Gerald I.
Author's Email Address gricha9@lsu.edu
URN etd-11142007-183128
Title The Use of a Chiral Fluorescent Resorcinarene for the Enantiomeric Recognition of Amino Acids
Degree Master of Science (M.S.)
Department Chemistry
Advisory Committee
Advisor Name Title
Isiah M. Warner Committee Chair
Michael Paul Tolocka Committee Member
Steven F. Watkins Committee Member
  • fluorescence spectroscopy
  • chemometrics
  • fluorescent sensor
  • chiral analysis
Date of Defense 2007-11-13
Availability unrestricted
The spectroscopic properties of a chiral boronic acid based resorcinarene macrocycle employed for chiral analysis were investigated. Specifically, the emission and excitation characteristics of tetraarylboronate resorcinarene macrocycle (TBRM) and its quantum yield were evaluated. The chiral selector TBRM was investigated as a chiral reagent for the enantiomeric discrimination of amino acids using steady-state fluorescence spectroscopy. Chiral recognition of amino acids in the presence of the macrocycle was based on diastereomeric complexes. Results demonstrated that TBRM had better chiral discrimination ability for lysine as compared to the other amino acids. Partial-least-squares regression modeling (PLS-1) of spectral data for macrocycle-lysine host-guest complexes was used to correlate the changes in the fluorescence emission for a set of calibration samples consisting of TBRM in the presence of varying enantiomeric compositions of lysine. In addition, validation studies were performed using an independently prepared set of samples with different enantiomeric compositions of lysine. The results of multivariate regression modeling indicated good prediction ability of lysine which was confirmed by a root-mean-square percent relative error (RMS%RE) of 5.8%.
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