Document Detail


Molecular recognition in synthetic polymers. Enantiomeric resolution of amide derivatives of amino acids on molecularly imprinted polymers.
MedLine Citation:
PMID:  2636894     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Molecular imprints were prepared using L-phenylalanine anilide as the print molecule and methacrylic acid as the functional monomer. Methacrylic acid interacts ionically with the primary amine of the print molecule and via hydrogen bonding with the amide function. In the HPLC mode such polymers were shown to exhibit efficient enantiomeric resolution of a racemic mixture of the original print molecule. Enantiomeric resolution was shown to be dependent on the ratio of methacrylic acid to print molecule in the pre-polymerization mixture and specific for the presence of both print molecule and functional monomer. Further analyses showed the importance of both the primary amino and amide functions in the correct stereochemistry for recognition and enantiomeric resolution of compounds on such polymers. Other amide derivatives of amino acids including p-nitroanilides, beta-naphthylamides and amides were recognized by such polymers, and enantiomeric resolution was obtained for amide derivatives of amino acid ranging from alanine to tryptophan on a single polymer. The implications of these findings with respect to the mechanism of recognition and the ability to predict enantiomeric resolution of molecules on molecularly imprinted polymers will be discussed.
Authors:
D J O'Shannessy; L I Andersson; K Mosbach
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of molecular recognition : JMR     Volume:  2     ISSN:  0952-3499     ISO Abbreviation:  J. Mol. Recognit.     Publication Date:  1989 Jul 
Date Detail:
Created Date:  1990-07-09     Completed Date:  1990-07-09     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9004580     Medline TA:  J Mol Recognit     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  1-5     Citation Subset:  IM    
Affiliation:
Department of Pure and Applied Biochemistry, University of Lund, Sweden.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / isolation & purification*
Chemical Phenomena
Chemistry
Chromatography, High Pressure Liquid
Hydrogen Bonding
Methacrylates
Phenylalanine / analogs & derivatives*
Polymers*
Stereoisomerism
Substrate Specificity
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Methacrylates; 0/Polymers; 15423-54-8/phenylalanine anilide; 63-91-2/Phenylalanine; 79-41-4/methacrylic acid

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


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