Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis

• Elisabeth Mairhofer,
• Elisabeth Fuchs and
• Ronald Micura

Beilstein J. Org. Chem. 2016, 12, 2556–2562, doi:10.3762/bjoc.12.250

• -amino-3-deazapurine and benzoyl-protected 1-O-acetylribose. The novel path is superior to previously described syntheses in terms of efficacy and ease of laboratory handling. Keywords: deazapurine nucleoside; nucleosidation; protection groups; ribozymes; Introduction The synthesis of 3-deazaadenosine

• nucleosidation of 4-chloroimidazo[4,5-c]pyridine and 1,2,3,5-tetraacetyl-ß-D-ribofuranose in the presence of chloro acetic acid to yield the corresponding 6-chloro-3-deazapurine nucleoside (Scheme 1) [22]. Subsequent attempts to convert the chlorine atom directly by amination under various conditions failed

• , p-toluenesulfonic acid (cat.), melt (160 °C), 5 to 10 min. b) NH3 in ethanol (saturated at −30 °C), 140 °C, 89 h [23] or NH3 (30% aq), 200 °C, 5 d, 80% [24]. Synthesis of tribenzoylated 6-azido-3-deazapurine nucleoside 2. a) LiN3 (1.3 equiv), N,N-dimethylformamide, 120 °C, 18 h, 76%. b) 1-O-Acetyl

Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ₀)

• Sabin Llona-Minguez and
• Simon P. Mackay

Beilstein J. Org. Chem. 2014, 10, 1333–1338, doi:10.3762/bjoc.10.135

• medicinal chemistry literature reveals >200 publications in the field. Additionally, PreQ0 meets all the criteria dictated by the “2-0” rule of kinase-likeness proposed by Aronov et al. [8]. It is likely that compounds derived from PreQ0 display kinase activity. 7-Deazapurine nucleoside chemistry has been