Polycyclic Aromatic DNA‐Base Surrogates: High‐Affinity Binding to an Adenine‐Specific Base‐Flipping DNA Methyltransferase

Abstract

Filling the hole is a strategy that confers high-affinity DNA binding to the M⋅TaqI DNA methyltransferase. Aromatic base surrogates (e.g. pyrene, red in picture) were introduced into DNA by means of organocuprate-mediated C-glycosylations. A new competitive binding assay revealed that DNA with aromatic base surrogates placed opposite to the target base binds to M⋅TaqI with up to 400-fold-enhanced affinity.