Document Detail


Determination of enantiomeric compositions of analytes using novel fluorescent chiral molecular micelles and steady state fluorescence measurements.
MedLine Citation:
PMID:  17985217     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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:
Alicia A Williams; Sayo O Fakayode; Onur Alptürk; Christina M Jones; Mark Lowry; Robert M Strongin; Isiah M Warner
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2007-11-06
Journal Detail:
Title:  Journal of fluorescence     Volume:  18     ISSN:  1053-0509     ISO Abbreviation:  J Fluoresc     Publication Date:  2008 Mar 
Date Detail:
Created Date:  2008-03-11     Completed Date:  2008-06-16     Revised Date:  2013-06-06    
Medline Journal Info:
Nlm Unique ID:  9201341     Medline TA:  J Fluoresc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  285-96     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
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MeSH Terms
Descriptor/Qualifier:
Chemistry, Physical
Circular Dichroism
Glucose / metabolism*
Micelles*
Molecular Structure
Phenylalanine / analogs & derivatives*,  chemical synthesis,  chemistry
Physicochemical Phenomena
Serine / metabolism*
Spectrometry, Fluorescence*
Stereoisomerism
Surface-Active Agents / chemistry*
Tartrates / metabolism*
Tryptophan / analogs & derivatives*,  chemical synthesis,  chemistry
Tyrosine / analogs & derivatives*,  chemical synthesis,  chemistry
Grant Support
ID/Acronym/Agency:
R01 EB002044/EB/NIBIB NIH HHS; R01 EB002044-07/EB/NIBIB NIH HHS
Chemical
Reg. No./Substance:
0/Micelles; 0/N-undecanoylphenylalanine; 0/N-undecanoyltryptophan; 0/N-undecanoyltyrosine; 0/Surface-Active Agents; 0/Tartrates; 50-99-7/Glucose; 55520-40-6/Tyrosine; 56-45-1/Serine; 63-91-2/Phenylalanine; 73-22-3/Tryptophan; W4888I119H/tartaric acid
Comments/Corrections

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