Isolation and identification of a fluorophore from ampicillin degradation.
A fluorescent impurity in ampicillin has been isolated and identified as 2-hydroxy-3-phenylpyrazine. The product is formed under acidic conditions similar to those employed in some fluorometric assay procedures. The mechanism of the reaction is proposed to involve cyclization by condensation of the penilloaldehyde of ampicillin. The structure was confirmed by independent synthesis.
D000667:Ampicillin / Q000032:analysis*; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004355:Drug Stability; D011719:Pyrazines / Q000032:analysis* / Q000138:chemical synthesis; D013050:Spectrometry, Fluorescence
D011719:Pyrazines; C020364:2-hydroxy-3-phenylpyrazine; D000667:Ampicillin