Reactions of 6-aminopenicillanic acid with carbohydrates and related substances

Abstract

6-Aminopenicillanic acid (6-APA) reacts with reducing sugars at room temperature and neutral pH to produce derivatives that are probably the N-glycosyl compounds of 6-APA. The properties of glu cosyl, maltosyl and lactosyl derivatives of 6-APA prepared as their Na salts were examined. These derivatives of 6-APA which are stable to both staphylococcal and Bacillus cereus penicillinase are readily hydrolyzed to the parent compounds by acid. Compounds behaving like those prepared from 6-APA and sugars were identified in both the culture filtrates and the mycelium of a culture of Penicillium chrysogenum grown under conditions in which it produced 6-APA.