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© Institut Pasteur
Cristaux de cellulase, enzyme purifiée de Clostridium thermocellum permettant la digestion de la cellulose. Image colorisée.
Publication : European Journal of Organic Chemistry

Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors: Biological evaluation and conformational analysis of 2 ‘- and 3 ‘-modified thymidine analogues

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in European Journal of Organic Chemistry - 01 Aug 2003

Van Rompaey, P., Nauwelaerts, K., Vanheusden, V., Rozenski, J., Munier-Lehmann, H., Herdewijn, P. and Van Calenbergh, S.

Eur. J. Org. Chem., 2003: 2911–2918. doi: 10.1002/ejoc.200300177

Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) has recently been introduced as a potential target for the structure-based design of anti-tuberculosis drugs. Based on the TMPKmt X-ray structure and previous S.A.R. studies, we synthesised the nucleoside analogues 3ab, 6ab, 7ab, and 8ab, modified in 2′- and 3′-position of the ribofuranose ring moiety. To our surprise, these analogues showed only moderate binding affinity (i.e. Ki between 118 and 1260 μM). This prompted us to investigate the conformational features of these nucleosides. We concluded that compounds of this series, especially 8ab, are strongly biased towards the “Northern” furanose ring conformation, whereas X-ray crystallography reveals a preference of TMPKmt for the opposite “Southern” conformers. This paper covers the synthesis, biological evaluation and conformational features (i.e. preferred ring puckering) of the 2′- and 3′-modified dT analogues.