Document Detail


Comparison of the separation efficiencies of chirobiotic T and TAG columns in the separation of unusual amino acids.
MedLine Citation:
PMID:  15058579     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Two macrocyclic antibiotic type chiral stationary phases (CSPs), based on native teicoplanin and teicoplanin aglycone, Chirobiotic T and Chirobiotic TAG, respectively, were evaluated for the high-performance liquid chromatographic separation of enantiomers of 15 unnatural conformationally constrained alpha-amino acids, Phe and Tyr analogs, and 12 beta-amino acids having cycloalkane or cycloalkene skeletons. The chromatographic results are given as the retention, separation and resolution factors along with the enantioselective free energy difference corresponding to the separation of the enantiomers. It is clearly established that in most cases the aglycone is responsible for the enantioseparation of amino acids. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP was between 0.02 and 0.30 kcal mol(-1) for these particular amino acids. The resolution factors are higher with the aglycone CSP. Although the sugar units generally decrease the resolution of amino acid enantiomers, they can contribute significantly to the resolution of some unusual amino acid analogs. By application of these two CSPs excellent resolutions were achieved for most of the investigated compounds by using reversed phase or polar organic mobile mode systems. The separation conditions were optimized by variation of the mobile phase composition.
Authors:
Antal Péter; Anita Arki; Dirk Tourwé; Eniko Forró; Ferenc Fülöp; Daniel W Armstrong
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of chromatography. A     Volume:  1031     ISSN:  0021-9673     ISO Abbreviation:  J Chromatogr A     Publication Date:  2004 Mar 
Date Detail:
Created Date:  2004-04-02     Completed Date:  2004-10-07     Revised Date:  2009-01-15    
Medline Journal Info:
Nlm Unique ID:  9318488     Medline TA:  J Chromatogr A     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  159-70     Citation Subset:  IM    
Affiliation:
Department of Inorganic and Analytical Chemistry, University of Szeged, Dómtér 7, H-6720 Szeged, Hungary. apeter@chem.u-szeged.hu
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry,  isolation & purification*
Anti-Bacterial Agents / chemistry*
Carbohydrates / chemistry
Chemistry, Physical
Chromatography, High Pressure Liquid
Indicators and Reagents
Kinetics
Molecular Conformation
Physicochemical Phenomena
Solvents
Stereoisomerism
Teicoplanin / chemistry*
Grant Support
ID/Acronym/Agency:
R01 GM53825-08/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Anti-Bacterial Agents; 0/Carbohydrates; 0/Indicators and Reagents; 0/Solvents; 61036-62-2/Teicoplanin

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


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