Polyene antibiotics. VII. Carbon-13 nuclear magnetic resonance evidence for cyclic hemiketals in the polyene antibiotics amphotericin B, nystatin A1, tetrin A, tetrin B, lucensomycin, and pimaricin1,2.
Carbon magnetic resonance establishes conclusively that six polyene macrolide antibiotics containing keto groups (the heptaene amphotericin B, the tetraene-diene nystatin A1, and the tetraenes tetrin A, tetrin B, pimaricin, and lucensomycin) exist in the hemiketal form in solution. Their spectra all contain a hemiketal carbon's absorption near 97 ppm but lack a keto carbon's absorption near 210 ppm. The non-polyenic macrolide erythromycin, on the other hand, exists in the keto form.
D000666:Amphotericin B / Q000032:analysis*; D000935:Antifungal Agents / Q000032:analysis*; D002247:Carbon Isotopes; D004917:Erythromycin / Q000032:analysis; D007783:Lactones / Q000032:analysis; D008155:Lucensomycin / Q000032:analysis*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D010866:Natamycin / Q000032:analysis*; D009761:Nystatin / Q000032:analysis*
D000935:Antifungal Agents; D002247:Carbon Isotopes; D007783:Lactones; D018942:Macrolides; D009761:Nystatin; C003421:tetrin B; C003420:tetrin A; D008155:Lucensomycin; D004917:Erythromycin; D000666:Amphotericin B; D010866:Natamycin