Synthesis and Properties of mRNA 5′-Cap Analogues with 7-Methylguanine Replaced by Benzimidazole or 3-Methylbenzimidazole

L. Chlebicka Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Warsaw, Poland; Department of Biophysics, University of Warsaw, Warsaw, Poland

Z. Wieczorek Department of Physics and Biophysics, Academy of Agriculture and Technology, Olsztyn, Poland

R. Stolarski Department of Biophysics, University of Warsaw, Warsaw, Poland

J. Stepinski Department of Chemistry, University of Warsaw, Warsaw, Poland

E. Darzynkiewicz Department of Biophysics, University of Warsaw, Warsaw, Poland

D. Shugar Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Warsaw, Poland; Department of Biophysics, University of Warsaw, Warsaw, Poland

Abstract

Several new analogues of the mRNA 5′-cap structure, m⁷G(5′)Pn(5′)N, with n = 2–4, have been synthesized in which the m⁷G component is replaced by 1-(β-D-ribofuranosyl)benzimidazole (RBz) or 3-methyl-RBz. The latter, like m⁷G, has a positively charged imidazole ring and is likewise fluorescent. All compounds have been characterized by various physico-chemical and enzymatic criteria, and by ¹H and ³¹P NMR spectroscopy.

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Synthesis and Properties of mRNA 5′-Cap Analogues with 7-Methylguanine Replaced by Benzimidazole or 3-Methylbenzimidazole

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Synthesis and Properties of mRNA 5′-Cap Analogues with 7-Methylguanine Replaced by Benzimidazole or 3-Methylbenzimidazole

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