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Highlighting the role of the chlorine substituents in the glycopeptide antibiotic balhimycin for chiral recognition in capillary electrophoresis
Author(s) -
Jiang Zhengjin,
Bertazzo Marcelo,
Süssmuth Roderich D.,
Yang Zhuohong,
Smith Norman Williams,
Schurig Volker
Publication year - 2006
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.200500625
Subject(s) - glycopeptide , capillary electrophoresis , antibiotics , glycopeptide antibiotic , chromatography , chemistry , combinatorial chemistry , chlorine , electrophoresis , stereochemistry , biochemistry , vancomycin , organic chemistry , bacteria , biology , genetics , staphylococcus aureus
Abstract 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.