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

S. Vichier-Guerre; L. Dugué; F. Bonhomme; S. Pochet

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, *}

* Corresponding author

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.

Document type :

Journal articles

Domain :

Chemical Sciences

Complete list of metadatas

https://hal-pasteur.archives-ouvertes.fr/pasteur-01614533
Contributor : Sophie Vichier-Guerre <>
Submitted on : Wednesday, October 11, 2017 - 9:53:49 AM
Last modification on : Thursday, January 11, 2018 - 6:25:29 AM

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

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

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