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Orthogonally Positioned Diamino Pyrrole- and Imidazole-Containing Polyamides: Synthesis of 1-(3-Substituted-propyl)-4-nitropyrrole-2-carboxylic Acid and 1-(3-Chloropropyl)-4-nitroimidazole-2-carboxylic Acid |
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| Authors: | Vijay Satam Pravin Patil Balaji Babu Toni Rice Alexander Porte Shannon Alger |
| Affiliation: | 1. Department of Chemistry , Hope College , Holland , Michigan , USA;2. Department of Chemistry , Youngstown State University , Youngstown , Ohio , USA |
| Abstract: | Pyrrole- and imidazole-containing polyamides can be tailored to recognize the DNA 6–8 base pair sequence. We found that adding a second amino group via the N1-position of pyrrole or imidazole in polyamides could enhance their DNA binding affinity and water solubility while retaining sequence specificity. Synthesis of the key 1-substituted-4-nitropyrrole (and imidazole)-2-carboxylic acid building blocks are described. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] |
| Keywords: | Diamino polyamides DNA binding imidazole pyrrole sequence specificity |