Synthesis of <i>O</i> ⁶-alkylated preQ₁ derivatives.

ABSTRACT: A naturally occurring riboswitch can utilize 7-aminomethyl-O ⁶-methyl-7-deazaguanine (m⁶preQ₁) as cofactor for methyl group transfer resulting in cytosine methylation. This recently discovered riboswitch-ribozyme activity opens new avenues for the development of RNA labeling tools based on tailored O ⁶-alkylated preQ₁ derivatives. Here, we report a robust synthesis for this class of pyrrolo[2,3-d]pyrimidines starting from readily accessible N ²-pivaloyl-protected 6-chloro-7-cyano-7-deazaguanine. Substitution of the 6-chloro atom with the alcoholate of interest proceeds straightforward. The transformation of the 7-cyano substituent into the required aminomethyl group turned out to be challenging an

SUBMITTER: Flemmich L 

PROVIDER: S-EPMC8450960 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature