Introduction of axial chirality in a planar aromatic ligand results in chiral recognition with DNA

✍ Scribed by Marc-André Dubois; Alain Grandbois; Shawn K. Collins; Andreea R. Schmitzer

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 777 KB
• Volume: 24
• Category: Article
• ISSN: 0952-3499
• DOI: 10.1002/jmr.1055

✦ Synopsis

Abstract

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. Copyright © 2010 John Wiley & Sons, Ltd.