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.
journal_name
J Mol Modeljournal_title
Journal of molecular modelingauthors
Duran D,Aviyente V,Baysal Cdoi
10.1007/s00894-003-0172-7subject
Has Abstractpub_date
2004-04-01 00:00:00pages
94-101issue
2eissn
1610-2940issn
0948-5023journal_volume
10pub_type
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