Original scientific paper

Conformational Behaviour of 11-O-Methylazithromycin in the Solid and Solution State

Nada Košutić-Hulita ; Laboratorj of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Ulica kralja Zvonimira 8, 10000 Zagreb, Croatia
Dijana Matak-Vinković ; Laboratorj of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Ulica kralja Zvonimira 8, 10000 Zagreb, Croatia
Mladen Vinković ; Analytical Centre, PLIVA-Research & Development, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia
Predrag Novak ; Analytical Centre, PLIVA-Research & Development, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia
Gabrijela Kobrehel ; Antiinfectives, PLIVA-Research & Development, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia
Gorjana Lazarevski ; Antiinfectives, PLIVA-Research & Development, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia

Abstract

Conformational behaviour of azithromycin 11-OMe derivative 2 (Scheme 1) has been studied in the solid and solution state. In the CDCl₃ and DMSO solution, 2 mainly adopts the »folded-in« conformation. 11-OMe group is oriented toward the centre of aglycone ring. The crystal structure of DMSO solvate of 2 has been solved by the molecular replacement method using the solution state conformation as the search model. Conformation of 2 in the solid and solution state is very similar. Molecules of 2 are held together in the crystal by van der Waals interactions, forming a solvent channel along the b axis. The DMSO molecule is found to be disordered and bound to cladinose moiety of 2 by H-bond O4"-H...01s.

Keywords

azithromycin; crystal structure; molecular replacement; NMR

Hrčak ID:

131826

URI

https://hrcak.srce.hr/131826

Publication date:

2.4.2001.

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