Identification and Synthesis of an Oxidation Product of Tilmicosin

• Published in: Journal of agricultural and food chemistry Vol. 46; no. 8; pp. 3265 - 3271
• Main Authors: Willard, Kevin E, Kirst, Herbert A, Leeds, James P, Readnour, Robin S, Klink, Paul R, Cleveland, Christine M, Kiehl, Douglas E
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.08.1998; Amer Chemical Soc
• Subjects: 12,13-EPOXYTILMICOSIN; Agriculture; Agriculture, Multidisciplinary; Analysis; Antibacterial agents; ANTIBIOTICOS; ANTIBIOTICS; Antibiotics. Antiinfectious agents. Antiparasitic agents; ANTIBIOTIQUE; Biological and medical sciences; CHEMICAL STRUCTURE; Chemistry; Chemistry, Applied; DESARROLLO DE UN PRODUCTO; DEVELOPPEMENT DE PRODUIT; DRUG FORMULATION DEVELOPMENT; ESTRUCTURA QUIMICA; Food Science & Technology; General pharmacology; IDENTIFICACION; IDENTIFICATION; Life Sciences & Biomedicine; MACROLIDE ANTIBIOTICS; Medical sciences; OXIDACION; OXIDATION; OXYDATION; Pharmacology. Drug treatments; Physical Sciences; PRODUCT DEVELOPMENT; Science & Technology; STRUCTURE CHIMIQUE; synthesis; epoxytilmicosin; SWINE; oxidation; EL-870; tilmicosin; PHOSPHATE; DISEASE; liquid chromatography ion spray mass spectrometry; CALVES; DERIVATIVES; FEED; macrolide; ACTINOBACILLUS-PLEUROPNEUMONIAE; Chemical analysis; Coupled method; Reaction product; Ion beam sputtering; Fragmentation pattern; Liquid chromatography; Veterinary medicine; In vitro; Macrolide; Biological activity; Antibiotic; Epoxide; Oxidation; Antibacterial agent; Mass spectrometry; Tilmicosin
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf9710746

During formulation development of the veterinary macrolide antibiotic tilmicosin, an oxidation product of the parent molecule was identified. Use of liquid chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy characterized the structure as 12,13-epoxytilmicosin, resulting from the oxidation of the double bond at the 12,13-position of the macrolide dienone. The synthesis of this oxidation product for confirmation of structural identity is described. The synthetic compound was identical to the isolated oxidation product, 12,13-epoxytilmicosin. Keywords: Tilmicosin; epoxytilmicosin; macrolide; oxidation; synthesis; liquid chromatography/ion spray mass spectrometry