New Efficient Synthesis of tRNA Related Adenosines Bearing the Hydantoin Ring (ct6 A, ms2 ct6 A) by Intramolecular Cyclization of N6 -(N-Boc-α-aminoacyl)-adenosine Derivatives.

Katarzyna Frankowska, Elzbieta Sochacka

Chembiochem : a European journal of chemical biology 2022 Mar 04

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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, Tf2 O-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 (ct6 A) and 2-methylthio-N6 -threonylcarbamoyladenosine (ms2 ct6 A) were prepared in good yields. © 2022 Wiley-VCH GmbH.

Citation

Katarzyna Frankowska, Elzbieta Sochacka. New Efficient Synthesis of tRNA Related Adenosines Bearing the Hydantoin Ring (ct6 A, ms2 ct6 A) by Intramolecular Cyclization of N6 -(N-Boc-α-aminoacyl)-adenosine Derivatives. Chembiochem : a European journal of chemical biology. 2022 Mar 04;23(5):e202100655