Jump to main content
Jump to site search

Issue 38, 2017
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Jul 2017, accepted on 12 Sep 2017 and first published on 12 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01850A
Citation: Org. Biomol. Chem., 2017,15, 8193-8203
  •   Request permissions

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

    S. Vichier-Guerre, L. Dugué, F. Bonhomme and S. Pochet, Org. Biomol. Chem., 2017, 15, 8193
    DOI: 10.1039/C7OB01850A

Search articles by author

Spotlight

Advertisements