Methylation at specific positions of the nucleobases provides the most common means by which genomic DNA is reversibly marked. Although epigenetic modification occurs most commonly at C in DNA, methylation at the N6-position of A (N6mdA) has also been identified in eukaryotes, including mammals, and could play an important role in gene expression and disease regulation. N6mdA displays the only secondary amine motif in DNA, but no methods exist for its functionalization. Herein, we report the development of a synthetic method that introduces a covalent modification at the methylated DNA residue N6mdA. As a demonstration of the remarkably selective chemistry, we are able to modify and enrich oligonucleotide fragments comprising N6mdA, which is also proof-of-concept for a previously unknown method in which this methylated nucleotide could be detected in DNA.

Chemical method for selective functionalization at N6mdA residues in DNA

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.