CONFORMATIONAL ANALYSIS AND STEREOCHEMICAL CONTROL IN MACROLIDES BY MOLECULAR MECHANICS AND BOLTZMANN DISTRIBUTION.

Authors

  • Salah Belaidi Group of Computational and Pharmaceutical Chemistry, Laboratory of Molecular Chemistry and Environment, University of Biskra, BP 145 Biskra 07000, Algeria
  • Fatima Daissa Group of Computational and Medicinal Chemistry, LMCE Laboratory, University of Biskra, 07000, Biskra, Algeria
  • Touhami Lanez VTRS Laboratory, University of Echahid Hamma Lakhdar, B.P.789, 39000, El Oued, Algeria

DOI:

https://doi.org/10.4314/jfas.1321

Keywords:

Macrolide, Molecular mechanics, PM3, Boltzmann distribution, Stereoselectivity

Abstract

The Conformational analysis and stereochemical control of 20-Membered Macrolides were investigated using molecular mechanics calculations, PM3 semi-empirical method, and Boltzmann distribution. The results indicate that these macrocycles have a high degree of conformational flexibility. However, in the presence of tricarbonyliron, the number of favorable conformations was reduced to only four. The study also revealed significant diastereoselectivity (73:27) in B-type complexed macrolides. Furthermore, it was observed that the methyl group in position α2 had a local conformational effect that increased the diastereoselectivity of alkylation reactions. The high diastereoselectivity observed was attributed to the combination of stereochemical remote control with Fe(CO)3 and local control by the methyl group.

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Published

2023-09-01

How to Cite

BELAIDI, S.; DAISSA , F. . .; LANEZ , T. . CONFORMATIONAL ANALYSIS AND STEREOCHEMICAL CONTROL IN MACROLIDES BY MOLECULAR MECHANICS AND BOLTZMANN DISTRIBUTION. Journal of Fundamental and Applied Sciences, [S. l.], v. 15, n. 3, p. 194–205, 2023. DOI: 10.4314/jfas.1321. Disponível em: https://jfas.info/index.php/JFAS/article/view/1321. Acesso em: 13 jul. 2024.

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