Introduction of axial chirality in a planar aromatic ligand results in chiral recognition with DNA.
Dimerization of a hydroxycarbazole produces an axially chiral biaryl, BICOL (2). One enantiomer (R)-2, is capable of enantioselective binding to different polymorphs of DNA. The biaryl (R)-2 was shown by fluorescence and circular dichroism to induce a shift of Z-DNA to B-DNA. The opposite enantiomer (S)-2 shows no specific binding. The significant difference in behaviour between the two enantiomers (S)-2 and (R)-2 is in line with molecular modelling studies which show two very different binding geometries between the enantiomers with each polymorph of DNA.
Dubois
Marc-André
MA
Department of Chemistry, Université de Montréal, C.P. 6128 Station Downtown, Montréal, Québec H3C 3J7, Canada.
Grandbois
Alain
A
Collins
Shawn K
SK
Schmitzer
Andreea R
AR
D002227:Carbazoles / Q000737:chemistry*; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D043542:DNA, Z-Form / Q000737:chemistry; D008024:Ligands; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics
D002227:Carbazoles; D043542:DNA, Z-Form; D008024:Ligands; D004247:DNA