Efficient access to N-trifluoroacetylated 2′-amino-2′-deoxyadenosine phosphoramidite for RNA solid-phase synthesis

ABSTRACT: Here, we present a robust synthetic route to a 2′-amino-2′-deoxyadenosine phosphoramidite building block for automated RNA solid-phase synthesis. The thus accessible 2′-amino-modified RNA finds applications in the evaluation of hydrogen-bond networks in folded RNA, such as riboswitches or ribozymes. In this context, we previously implemented the here described 2′-amino-2′-deoxyadenosine building block in a comparative study on self-cleaving pistol ribozymes to shed light on structural versus catalytic roles of active-site 2′-OH groups in the reaction mechanism. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-019-02390-x) contains supplementary material, which is available to authorized users.