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Nucleic Acids Research, 2001, Vol. 29, No. 10 2199-2204
© 2001 Oxford University Press

Efficient new ribozyme mimics: direct mapping of molecular design principles from small molecules to macromolecular, biomimetic catalysts

William C. Putnam, Andrew T. Daniher, Bobby N. Trawick and James K. Bashkin*

Department of Chemistry, Washington University, St Louis, MO 63130-4899, USA

Dramatic improvements in ribozyme mimics have been achieved by employing the principles of small molecule catalysis to the design of macromolecular, biomimetic reagents. Ribozyme mimics derived from the ligand 2,9-dimethylphenanthroline (neocuproine) show at least 30-fold improvements in efficiency at sequence-specific RNA cleavage when compared with analogous o-phenanthroline- and terpyridine-derived reagents. The suppression of hydroxide-bridged dimers and the greater activation of coordinated water by Cu(II) neocuproine (compared with the o-phananthroline and terpyridine complexes) better allow Cu(II) to reach its catalytic potential as a biomimetic RNA cleavage agent. This work demonstrates the direct mapping of molecular design principles from small-molecule cleavage to macromolecular cleavage events, generating enhanced biomimetic, sequence-specific RNA cleavage agents.

* To whom correspondence should be addressed at present address: Pharmacia Corporation R3A, 800 North Lindbergh Boulevard, St Louis, MO 63167, USA. Tel: +1 314 694 3244; Fax: +1 314 694 3479; Email: james.k.bashkin{at}pharmacia.com Present addresses:William C. Putnam, Midwest Research Institute, 425 Volker Boulevard, Kansas City, MO 64110, USABobby N. Trawick, MetaPhore Pharmaceuticals, Inc., 1910 Innerbelt Business Center Drive, St Louis, MO 63114, USA


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