67616-36-8Relevant academic research and scientific papers
An expedient synthesis of flexible nucleosides: Via a regiocontrolled enzymatic glycosylation of functionalized imidazoles
Vichier-Guerre,Dugué,Bonhomme,Pochet
, p. 8193 - 8203 (2017)
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.
Recognition of all four base pairs of double-helical DNA by triple-helix formation: Design of nonnatural deoxyribonucleosides for pyrimidine-purine base pair binding
Griffin, Linda C.,Kiessling, Laura L.,Beal, Peter A.,Gillespie, Paul,Dervan, Peter B.
, p. 7976 - 7982 (2007/10/02)
The sequence-specific recognition of double-helical DNA by oligonuclcotide-directed triple-helix formation is limited mostly to purine tracts. Design leads that could expand the recognition code to all four Watson-Crick base pairs would provide one step t
