Document Detail


Highlighting the role of the chlorine substituents in the glycopeptide antibiotic balhimycin for chiral recognition in capillary electrophoresis.
MedLine Citation:
PMID:  16470757     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The vancomycin-type glycopeptide antibiotic balhimycin (I) and its dehaloanalogue dechlorobalhimycin (III), which is characterized by the total substitution of the two chlorine atoms of I by hydrogen, were employed as chiral selectors for the enantioresolution of 11 racemic dansyl amino acids and six 2-arylpropionic acid nonsteroidal anti-inflammatory racemic drugs by CE. The observed enantioresolution capability of I for all test analytes is clearly higher than that observed for III. This result suggests that chlorine substituents of I played a major role in the enantioresolution of these test analytes. A dimerization-based mechanism is proposed in order to explain this phenomenon. The two chlorine substituents of each monomer, which mutually penetrate into the cavity of the adjacent molecule of the dimer, are assumed to promote dimerization and as a consequence also enantioresolution.
Authors:
Zhengjin Jiang; Marcelo Bertazzo; Roderich D Süssmuth; Zhuohong Yang; Norman Williams Smith; Volker Schurig
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Electrophoresis     Volume:  27     ISSN:  0173-0835     ISO Abbreviation:  Electrophoresis     Publication Date:  2006 Mar 
Date Detail:
Created Date:  2006-03-27     Completed Date:  2006-05-25     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8204476     Medline TA:  Electrophoresis     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1154-62     Citation Subset:  IM    
Affiliation:
Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany.
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MeSH Terms
Descriptor/Qualifier:
Anti-Bacterial Agents / chemistry*
Binding Sites
Binding, Competitive
Chlorine / chemistry
Electrophoresis, Capillary / methods*
Ligands
Molecular Structure
Stereoisomerism
Vancomycin / analogs & derivatives*,  chemistry
Chemical
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Ligands; 1404-90-6/Vancomycin; 140932-79-2/balhimycin; 7782-50-5/Chlorine

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


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