To date, the concept of DNA-based
asymmetric catalysis has been
successfully applied to various synthetic transformations by way of
hybrid catalysts involving either an intercalator or an integrated
ligand anchored through supramolecular interactions. We report here
a new anchoring strategy based on the well-known groove-binder Hoechst
33258. The interaction between calf thymus DNA (ct-DNA) and poly[d(A-T)2] with a series of Hoechst 33258-derived ligands was studied
by UV–vis absorption spectroscopy, thermal melting analysis,
fluorescence emission, CD spectroscopy, mass spectrometry, and molecular
docking. The results clearly show that a groove-binding anchoring
strategy can be envisioned for DNA-based asymmetric catalysis, offering
additional mechanistic insight on how the intrinsic chirality of DNA
can be transferred to a reaction product. Most importantly, this new
anchoring strategy offers interesting compartmentalization possibilities
and provides a new way to reverse the enantioselectivity outcome of
a given reaction.
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