An expedient synthesis of flexible nucleosides via a regiocontrolled enzymatic glycosylation of functionalized imidazoles - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2017

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

(1) , (1) , (1) , (1)
1
S. Vichier-Guerre
L. Dugué
  • Function : Author
S. Pochet
  • Function : Correspondent author
  • PersonId : 852562

Connectez-vous pour contacter l'auteur

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.
Not file

Dates and versions

pasteur-01614533 , version 1 (11-10-2017)

Identifiers

Cite

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

Collections

PASTEUR CNRS
32 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More