Abstract
AbstractA simple and efficient synthesis of dinucleotide mRNA 5′ cap analogues functionalised by the addition of an amine or carboxylic acid group onto one of the ribose rings is reported. Selection of the modification sites was dictated by the recognition specificity for the 5′ cap by various cap‐binding proteins, including eIF4E, DcpS, and Dcp2, as well as by bacteriophage RNA polymerase, which enables the incorporation of the synthetic cap into the mRNA chain. Some analogues were further modified by O‐to‐CH2 substitution in the triphosphate bridge to confer resistance to specific hydrolases. Spatial crowding and structural rigidity were balanced by use of diamines and amino acids of different lengths attached to the ribose through a carbamate moiety. The impact of these substitutions on the conformational equilibria of the ribose components was investigated by 1H NMR spectroscopy. The utility of the analogues for labelling with fluorescent dyes and affinity tags was demonstrated with the aid of NHS activation chemistry.
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