Journal of Molecular Modeling

, Volume 10, Issue 2, pp 94–101

A computational approach to the synthesis of dirithromycin

Original Paper

DOI: 10.1007/s00894-003-0172-7

Cite this article as:
Duran, D., Aviyente, V. & Baysal, C. J Mol Model (2004) 10: 94. doi:10.1007/s00894-003-0172-7

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.

Figure Synthesis of dirithromycin

Keywords

DirithromycinEpidirithromycinSchiff baseRing–chain tautomerizationEpimerization

Copyright information

© Springer-Verlag 2004

Authors and Affiliations

  1. 1.Chemistry Department, Faculty of Art and SciencesBoğaziçi UniversityIstanbulTurkey
  2. 2.Laboratory of Computational Biology, Faculty of Engineering and Natural SciencesSabanci UniversityIstanbulTurkey