| Determination of enantiomeric compositions of analytes using novel fluorescent chiral molecular micelles and steady state fluorescence measurements. | |
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MedLine Citation:
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PMID: 17985217 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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%. |
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Authors:
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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:
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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:
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Title: Journal of fluorescence Volume: 18 ISSN: 1053-0509 ISO Abbreviation: J Fluoresc Publication Date: 2008 Mar |
Date Detail:
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Created Date: 2008-03-11 Completed Date: 2008-06-16 Revised Date: 2011-09-26 |
Medline Journal Info:
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Nlm Unique ID: 9201341 Medline TA: J Fluoresc Country: United States |
Other Details:
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Languages: eng Pagination: 285-96 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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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:
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R01 EB002044-07/EB/NIBIB NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Micelles; 0/N-undecanoylphenylalanine; 0/N-undecanoyltryptophan; 0/N-undecanoyltyrosine; 0/Surface-Active Agents; 0/Tartrates; 50-99-7/Glucose; 526-83-0/tartaric acid; 55520-40-6/Tyrosine; 56-45-1/Serine; 63-91-2/Phenylalanine; 73-22-3/Tryptophan |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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