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Alternative Heterocycles for DNA Recognition: A 3-Pyrazole/Pyrrole Pair Specifies for G·C Base Pairs

Zhan, Zheng-Yun J. and Dervan, Peter B. (2000) Alternative Heterocycles for DNA Recognition: A 3-Pyrazole/Pyrrole Pair Specifies for G·C Base Pairs. Bioorganic and Medicinal Chemistry, 8 (10). pp. 2467-2474. ISSN 0968-0896. https://resolver.caltech.edu/CaltechAUTHORS:20160510-091108944

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Abstract

Synthetic ligands comprising three aromatic amino acids, pyrrole (Py), imidazole (Im), and hydroxypyrrole (Hp), specifically recognize predetermined sequences as side-by-side pairs in the minor groove of DNA. To expand the repertoire of aromatic rings that may be utilized for minor groove recognition, three five-membered heterocyclic rings, 3-pyrazolecarboxylic acid (3-Pz), 4-pyrazolecarboxylic acid (4-Pz), and furan-2-carboxylic acid (Fr), were examined at the N-terminus of eight-ring hairpin polyamide ligands. The DNA binding properties of 3-Pz, 4-Pz, and Fr each paired with Py were studied by quantitative DNase I footprinting titrations on a 283 bp DNA restriction fragment containing four 6-bp binding sites 5′-A TNCCTAA-3′ (N=G, C, A, or T; 6-bp polyamide binding site is underlined). The pair 3-Pz/Py has increased binding affinity and sequence specificity for G·C bp compared with Im/Py.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0968-0896(00)00182-6DOIArticle
http://www.sciencedirect.com/science/article/pii/S0968089600001826PublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2000 Elsevier Science Ltd. Received 3 April 2000; accepted 16 June 2000. We are grateful to the National Institutes of Health (GM-27681) for research support.
Funders:
Funding AgencyGrant Number
NIHGM-27681
Issue or Number:10
Record Number:CaltechAUTHORS:20160510-091108944
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160510-091108944
Official Citation:Zheng-Yun J Zhan, Peter B Dervan, alternative heterocycles for dna recognition: a 3-pyrazole/pyrrole pair specifies for g·c base pairs, Bioorganic & Medicinal Chemistry, Volume 8, Issue 10, October 2000, Pages 2467-2474, ISSN 0968-0896, http://dx.doi.org/10.1016/S0968-0896(00)00182-6. (http://www.sciencedirect.com/science/article/pii/S0968089600001826)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66846
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:18 May 2016 20:44
Last Modified:26 Nov 2019 11:15

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