Issue 66, 2018

A new water soluble copper N-heterocyclic carbene complex delivers mild O6G-selective RNA alkylation

Abstract

We show here that copper carbenes generated from diazo acetamides alkylate single RNAs, mRNAs, or pools of total transcriptome RNA, delivering exclusively alkylation at the O6 position in guanine (O6G). Although the reaction is effective with free copper some RNA fragmentation occurs, a problem we resolve by developing a novel water-stable copper N-heterocyclic carbene complex. Carboxymethyl adducts at O6G are known mutagenic lesions in DNA but their relevance in RNA biochemistry is unknown. As a case-in-point we re-examine an old controversy regarding whether O6G damage in RNA is susceptible to direct RNA repair.

Graphical abstract: A new water soluble copper N-heterocyclic carbene complex delivers mild O6G-selective RNA alkylation

Supplementary files

Article information

Article type
Communication
Submitted
05 Jun 2018
Accepted
24 Jul 2018
First published
25 Jul 2018

Chem. Commun., 2018,54, 9174-9177

A new water soluble copper N-heterocyclic carbene complex delivers mild O6G-selective RNA alkylation

D. Rasale, K. Patil, B. Sauter, S. Geigle, S. Zhanybekova and D. Gillingham, Chem. Commun., 2018, 54, 9174 DOI: 10.1039/C8CC04476G

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