Document Detail

Effect of alkylimidazolium substituents on enantioseparation ability of single-isomer alkylimidazolium-beta-cyclodextrin derivatives in capillary electrophoresis.
MedLine Citation:
PMID:  17386669     Owner:  NLM     Status:  MEDLINE    
A family of 6-mono(3-alkylimidazolium)-beta-cyclodextrins with one primary hydroxyl group replaced by an alkylimidazolium cation has been developed. The effect of alkyl substitutents on the enantioresolution ability of these single-isomer cyclodextrins towards dansyl amino acids has been studied by capillary electrophoresis. Systematical investigations on the effect of buffer pH and selector concentration on the enatioseparation show that chiral selectors with a shorter alkyl chain (R=C(n)H(2n+1), n</=4) presented more powerful chiral recognition ability. These newly introduced single-isomer beta-cyclodextrin derivatives proved to be effective chiral selectors for most selected dansyl amino acids at low buffer pH (e.g. pH 5.0) with selector concentration no less than 3mM. The apparent complex stability constants between alkylimidazolium beta-CDs and dansyl amino acids were also theoretically determined by using the mobility difference model proposed by Wren and Rowe. The side alkyl chains from both dansyl amino acids and alkylimidazolium beta-CDs displayed significant effect on the apparent complex stability constants. Both the optimum selector concentrations calculated according to the model, however, were much lower than the experimental values giving the maximum chiral resolution of enantiomers.
Weihua Tang; Teng-Teng Ong; I Wayan Muderawan; Siu Choon Ng
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-01-07
Journal Detail:
Title:  Analytica chimica acta     Volume:  585     ISSN:  1873-4324     ISO Abbreviation:  Anal. Chim. Acta     Publication Date:  2007 Mar 
Date Detail:
Created Date:  2007-03-27     Completed Date:  2007-07-06     Revised Date:  2009-11-19    
Medline Journal Info:
Nlm Unique ID:  0370534     Medline TA:  Anal Chim Acta     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  227-33     Citation Subset:  IM    
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
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MeSH Terms
Acetates / chemistry
Amino Acids / chemistry
Chemistry Techniques, Analytical / methods*
Electrophoresis, Capillary / methods*
Hydrogen-Ion Concentration
Imidazoles / chemistry*
Models, Chemical
beta-Cyclodextrins / chemistry*,  isolation & purification*
Reg. No./Substance:
0/Acetates; 0/Amino Acids; 0/Buffers; 0/Electrolytes; 0/Imidazoles; 0/beta-Cyclodextrins; 7585-39-9/betadex

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

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