Highlighting the role of the chlorine substituents in the glycopeptide antibiotic balhimycin for chiral recognition in capillary electrophoresis

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 si...

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Bibliographic Details
Published in:Electrophoresis 2006-03, Vol.27 (5-6), p.1154-1162
Main Authors: Jiang, Zhengjin, Bertazzo, Marcelo, Süssmuth, Roderich D., Yang, Zhuohong, Smith, Norman Williams, Schurig, Volker
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
Balhimycin
Binding Sites
Binding, Competitive
Capillary electrophoresis
Chlorine - chemistry
Electrophoresis, Capillary - methods
Enantioseparation
Glycopeptide antibiotics
Ligands
Molecular Structure
Stereoisomerism
Vancomycin - analogs & derivatives
Vancomycin - chemistry
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Summary: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.
ISSN:0173-0835
1522-2683
DOI:10.1002/elps.200500625