| Title | A computational approach to the synthesis of dirithromycin. | | Author(s) | Duran D, Aviyente V, Baysal C | | Institution | Chemistry Department, Faculty of Art and Sciences, Boğaziçi University, Bebek, 34342 Istanbul, Turkey. | | Source | J Mol Model (Online) 2004 Apr; 10(2):94-101. | | MeSH | Computational Biology
Erythromycin
Models, Chemical
Models, Molecular
Molecular Conformation
Research Support, Non-U.S. Gov't
Schiff Bases
| | 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. | | Language | eng | | Pub Type(s) | Journal Article
| | PubMed ID | 14722740 |
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