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A novel and efficient way for the synthesis of N6‐hydantoin‐modified adenosines, which utilizes readily available N6‐(N‐Boc‐α‐aminoacyl)‐adenosine derivatives, was developed. The procedure is based on the epimerization‐free, Tf2O‐mediated conversion of the… Click to show full abstract
A novel and efficient way for the synthesis of N6‐hydantoin‐modified adenosines, which utilizes readily available N6‐(N‐Boc‐α‐aminoacyl)‐adenosine derivatives, was developed. The procedure is based on the epimerization‐free, Tf2O‐mediated conversion of the Boc group into an isocyanate moiety, followed by intramolecular cyclization. Using this method two recently discovered hydantoin modified tRNA adenosines, that is, cyclic N6‐threonylcarbamoyl‐adenosine (ct6A) and 2‐methylthio‐N6‐threonylcarbamoyladenosine (ms2ct6A) were prepared in good yields.
Journal Title: ChemBioChem
Year Published: 2022
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