title: Determination of enantiomeric compositions of analytes using novel fluorescent chiral molecular micelles and steady state fluorescence measurements.
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%.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Alicia A
authors.initials: AA
authors.lastname: Williams
authors.forename: Sayo O
authors.initials: SO
authors.lastname: Fakayode
authors.forename: Onur
authors.initials: O
authors.lastname: Alptürk
authors.forename: Christina M
authors.initials: CM
authors.lastname: Jones
authors.forename: Mark
authors.initials: M
authors.lastname: Lowry
authors.forename: Robert M
authors.initials: RM
authors.lastname: Strongin
authors.forename: Isiah M
authors.initials: IM
authors.lastname: Warner
mesh_terms: D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002942:Circular Dichroism; D005947:Glucose / Q000378:metabolism*; D008823:Micelles; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012694:Serine / Q000378:metabolism*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D013644:Tartrates / Q000378:metabolism*; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D008823:Micelles; C529515:N-undecanoylphenylalanine; C529513:N-undecanoyltryptophan; C529514:N-undecanoyltyrosine; D013501:Surface-Active Agents; D013644:Tartrates; D014443:Tyrosine; D012694:Serine; D010649:Phenylalanine; D014364:Tryptophan; D005947:Glucose; C029768:tartaric acid