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 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.
Jiang
Zhengjin
Z
Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany.
Bertazzo
Marcelo
M
Süssmuth
Roderich D
RD
Yang
Zhuohong
Z
Smith
Norman Williams
NW
Schurig
Volker
V
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001665:Binding Sites; D001667:Binding, Competitive; D002713:Chlorine / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000737:chemistry
D000900:Anti-Bacterial Agents; D008024:Ligands; C087127:balhimycin; D002713:Chlorine; D014640:Vancomycin