Document Detail

Simultaneous enantiomeric determination of dansyl-D,L-phenylalanine by fluorescence spectroscopy in the presence of alpha-acid glycoprotein.
MedLine Citation:
PMID:  10361495     Owner:  NLM     Status:  MEDLINE    
Few techniques are amenable to real-time analysis of enantiomers. In this paper, total complexation by alpha-acid glycoprotein (AGP) is shown to discriminate between enantiomers of dansyl-D,L-phenylalanine (DPs) by changing the local environment of the D and L enantiomers (DDP and DLP, respectively) from hydrophilic to hydrophobic. DDP and DLP show the same native fluorescence at lambda ex/lambda em = 200/544 nm in the absence of AGP, but show shifted emissions with a component at lambda ex/lambda em = 220/497 nm in the presence of AGP and in lipophilic solutions. The conditions for an analytical determination have been optimized, and the method has been used to measure the enantiomeric composition of DDP/DLP mixtures with concentration ratios varying over 2 orders of magnitude. The mechanism of chiral recognition for DDP and DLP by AGP is discussed and should be equally applicable to other dansyl-derivative amino acid enantiomers. The association constants for AGP with DDP and with DLP have been determined to be 1.33 x 10(2) L g-1 and 2.29 x 10(2) L g-1, respectively.
Y Yan; M L Myrick
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Analytical chemistry     Volume:  71     ISSN:  0003-2700     ISO Abbreviation:  Anal. Chem.     Publication Date:  1999 May 
Date Detail:
Created Date:  1999-07-27     Completed Date:  1999-07-27     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0370536     Medline TA:  Anal Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1958-62     Citation Subset:  IM    
Department of Chemistry and Biochemistry, University of South Carolina, Columbia 29208, USA.
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MeSH Terms
Dansyl Compounds / analysis*
Indicators and Reagents
Orosomucoid / analysis*
Phenylalanine / analogs & derivatives*,  analysis
Spectrometry, Fluorescence
Reg. No./Substance:
0/Dansyl Compounds; 0/Indicators and Reagents; 0/Orosomucoid; 0/dansyl-phenylalanine; 63-91-2/Phenylalanine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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