Erythromycin A Enol Ether (Erythromycin EP Impurity E) is an impurity of Erythromycin.
Erythromycin A enol ether is a degradation product of erythromycin formed under acidic conditions by C6–OH internal attack on the C9 ketone to produce a cyclic enol ether. The rearrangement results in a loss of antibiotic activity. This single reaction was the prime driver for the development of second and third generation erythromycins. Erythromycin A enol ether is an important standard for stability studies.
ChEBI: Erythromycin a enol ether is an aminoglycoside.
erythromycin a enol ether, also known as 8,9-anhydroerythromycin a 6,9 hemiketal, is a kind of catabolite of erythromycin a without its antibiotic properties.erythromycin a enol ether functions as a β-turn mimic of the peptide hormone motilin which leads to duodenal contractions. erythromycin a enol ether is also the agent of gastrointestinal (gi) distress [1].motilin is a kind of polypeptide hormone with 22-amino acid belonging to the motilin family. motilin could increase the migrating myoelectric complex of gastrointestinal motility, and stimulate the pepsin production. motilin could also improve peristalsis in the small intestine and empty the gut for the next meal. besides, motilin could facilitate the release of somatostatin and pancreatic polypeptide.
[1] steinmetz w e, shapiro b l, roberts j j, et al. the structure of erythromycin enol ether as a model for its activity as a motilide.[j]. journal of medicinal chemistry, 2002, 45(22): 4899-4902.
