Chenoweth, David M. and Harki, Daniel A. and Dervan, Peter B. (2009) Oligomerization Route to Py-Im Polyamide Macrocycles. Organic Letters, 11 (16). pp. 3590-3593. ISSN 1523-7060 http://resolver.caltech.edu/CaltechAUTHORS:20090826-112850226
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Cyclic eight-ring pyrrole−imidazole polyamides are sequence-specific DNA-binding small molecules that are cell permeable and can regulate endogenous gene expression. Syntheses of cyclic polyamides have been achieved by solid-phase and solution-phase methods. A rapid solution-phase oligomerization approach to eight-ring symmetrical cyclic polyamides yields 12- and 16-membered macrocycles as well. A preference for DNA binding by the 8- and 16-membered oligomers was observed over the 12-ring macrocycle, which we attributed to a conformational constraint not present in the smaller and larger systems.
|Additional Information:||Copyright © 2009 American Chemical Society. Received June 11, 2009. Publication Date (Web): July 23, 2009. This work was supported by the National Institutes of Health (GM27681). D.M.C. is grateful for a Caltech Kanel predoctoral fellowship. D.A.H. thanks the California Tobacco-Related Disease Research Program (16FT-0055) for a postdoctoral fellowship. Supporting Information: Compound characterization, Figure S1, Figure S2, and experimental procedures. This material is available free of charge via the Internet at http://pubs.acs.org.|
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|Deposited By:||George Porter|
|Deposited On:||11 Sep 2009 18:38|
|Last Modified:||26 Dec 2012 11:15|
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