title: A computational approach to the synthesis of dirithromycin.
abstract: Dirithromycin is a macrolide antibiotic derived from erythromycin A. Dirithromycin is synthesized by the condensation of 9(S)-erythromycylamine with 2-(2-methoxyethoxy)-acetaldehyde. To gain insight into the synthesis, the condensation mechanism has been analyzed computationally by the AM1 method in the gas phase. First, the formation of the Schiff bases of dirithromycin and epidirithromycin from 9(S)-erythromycylamine and 2-(2-methoxyethoxy)-acetaldehyde were modeled. Then, the tautomerization of the Schiff bases to dirithromycin and epidirithromycin were considered. Finally, the epimerization of the Schiff base of epidirithromycin to the Schiff base of dirithromycin was investigated. Our results show that, even though carbinolamine forms faster for epidirithromycin than the corresponding structure for dirithromycin, dirithromycin is the major product of the synthesis.
authors.affiliation: Chemistry Department, Faculty of Art and Sciences, Boğaziçi University, Bebek, 34342 Istanbul, Turkey.
authors.forename: Dilek
authors.initials: D
authors.lastname: Duran
authors.forename: Viktorya
authors.initials: V
authors.lastname: Aviyente
authors.forename: Canan
authors.initials: C
authors.lastname: Baysal
mesh_terms: D019295:Computational Biology / Q000379:methods*; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D012545:Schiff Bases; C053853:dirithromycin; D004917:Erythromycin