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Journal articles
An expedient synthesis of flexible nucleosides via a regiocontrolled enzymatic glycosylation of functionalized imidazoles
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.
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 : Monday, January 11, 2021 - 2:30:05 PM
Contributor : Sophie Vichier-Guerre <>
Submitted on : Wednesday, October 11, 2017 - 9:53:49 AM
Last modification on : Monday, January 11, 2021 - 2:30:05 PM