Link between biological signaling and increased enantioseparations of acids using glycopeptide antibiotics.
The vancomycin analog A82846B has been shown to provide excellent selectivity as a chiral recognition agent for some acidic test analytes in capillary electrophoresis (CE) and high-performance liquid chromatography (HPLC). In both modes A82846B outperforms vancomycin as a chiral selector. A82846B has enhanced antibacterial activity data in comparison to vancomycin, which is probably due to the increased dimerization constant of over 100 in magnitude in comparison to vancomycin. The link between the electrophoretic and chromatographic separations observed and the biological activity of A82846B is discussed. Dimerization of A82846B in solution was proposed as a theory as to why A82846B gave such enhanced separations for acidic racemates. Further literature and experimental studies support the theory.
Reilly
J
J
Eli Lilly and Company, Erl Wood Manor, Windlesham, Surrey, UK. Reilly_John_x1@lilly.com
Sanchez-Felix
M
M
Smith
N W
NW
D000143:Acids / Q000737:chemistry / Q000302:isolation & purification*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D001665:Binding Sites; D002851:Chromatography, High Pressure Liquid; D019281:Dimerization; D019075:Electrophoresis, Capillary; D006020:Glycopeptides; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006583:Hexadimethrine Bromide; D008024:Ligands; D015398:Signal Transduction; D013237:Stereoisomerism; D014640:Vancomycin / Q000737:chemistry / Q000494:pharmacology
D000143:Acids; D000900:Anti-Bacterial Agents; D006020:Glycopeptides; D008024:Ligands; C053759:eremomycin; D006583:Hexadimethrine Bromide; D014640:Vancomycin