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

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 specifi...

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Published inSynthetic communications Vol. 44; no. 7; pp. 968 - 975
Main Authors Satam, Vijay, Patil, Pravin, Babu, Balaji, Rice, Toni, Porte, Alexander, Alger, Shannon, Zeller, Matthias, Lee, Moses
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis Group 03.04.2014
Taylor & Francis Ltd
Subjects
Diamino polyamides
DNA binding
imidazole
pyrrole
sequence specificity
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Summary: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.]
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2013.839795