New Efficient Synthesis of tRNA Related Adenosines Bearing the Hydantoin Ring (ct6A, ms2ct6A) by Intramolecular Cyclization of N6-(N-Boc-α-aminoacyl)-adenosine Derivatives

A novel and efficient way for the synthesis of N-6-hydantoin-modified adenosines, which utilizes readily available N-6-(N-Boc-alpha-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 N-6-threonylcarbamoyl-adenosine (ct(6)A) and 2-methylthio-N-6-threonylcarbamoyladenosine (ms(2)ct(6)A) were prepared in good yields.

Automated summary

A novel and efficient method for synthesizing N-6-hydantoin-modified adenosines has been developed. The method utilizes readily available adenosine derivatives and involves a series of reactions to obtain the desired products.