An expedient synthesis of flexible nucleosides via a regiocontrolled enzymatic glycosylation of functionalized imidazoles

S. Vichier-Guerre 1 L. Dugué 1 F. Bonhomme 1 S. Pochet 1, *
* Auteur correspondant
Abstract : A versatile two-step synthesis of C4- and C5-arylated 2′-deoxyribosylimidazoles was elaborated using enzymatic N-transglycosylation followed by microwave-assisted Pd-catalysed arylation reactions. We report herein the reaction conditions that permit managing regioselectivity (N3 versus N1-isomers) in the enzymatic glycosylation of 4-iodoimidazole using the nucleoside N-deoxyribosyltransferase from L. leichmannii. Regiocontrolled glycosylation was also observed among several other imidazole derivatives studied, providing simple access to isomers not readily accessible by chemical routes. Finally, a series of flexible nucleosides was obtained in one step from 4- or 5-iodo-imidazole nucleosides by the Suzuki–Miyaura cross-coupling reaction with (hetero)aryl-boronic acids in aqueous media. Moreover, this chemoenzymatic approach is compatible with a one-pot two-step process affording a straightforward access to a broad array of potential anticancer and antiviral drugs as well as new DNA building blocks.
Type de document :
Article dans une revue
Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2017, 15 (38), pp.8193 - 8203. 〈10.1039/C7OB01850A〉
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https://hal-pasteur.archives-ouvertes.fr/pasteur-01614533
Contributeur : Sophie Vichier-Guerre <>
Soumis le : mercredi 11 octobre 2017 - 09:53:49
Dernière modification le : jeudi 11 janvier 2018 - 06:25:29

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S. Vichier-Guerre, L. Dugué, F. Bonhomme, S. Pochet. An expedient synthesis of flexible nucleosides via a regiocontrolled enzymatic glycosylation of functionalized imidazoles. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2017, 15 (38), pp.8193 - 8203. 〈10.1039/C7OB01850A〉. 〈pasteur-01614533〉

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