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Expanding the Repertoire of Natural Product-Inspired Ring Pairs for Molecular Recognition of DNA

Muzikar, Katy A. and Meier, Jordan L. and Gubler, Daniel A. and Raskatov, Jevgenij A. and Dervan, Peter B. (2011) Expanding the Repertoire of Natural Product-Inspired Ring Pairs for Molecular Recognition of DNA. Organic Letters, 13 (20). pp. 5612-5615. ISSN 1523-7060. PMCID PMC3195311. https://resolver.caltech.edu/CaltechAUTHORS:20111122-075248586

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Abstract

A furan amino acid, inspired by the recently discovered proximicin natural products, was incorporated into the scaffold of a DNA-binding hairpin polyamide. While unpaired oligomers of 2,4-disubstituted furan amino acids show poor DNA-binding activity, furan (Fn) carboxamides paired with N-methylpyrrole (Py) and N-methylimidazole (Im) rings demonstrate excellent stabilization of duplex DNA as well as discrimination of noncognate sequences, consistent with function as a Py mimic according to the Py/Im polyamide pairing rules.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol202285yDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol202285yPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3195311/PubMed CentralArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2011 American Chemical Society. ACS AuthorChoice. Received August 30, 2011. Publication Date (Web): September 29, 2011. We are grateful to the National Institutes of Health(GM27681) for research support. J.L.M. (PF-10-015-01-CDD) and D.A.G. (PF-09-262-01-CDD) were supported by postdoctoral fellowships from the American Cancer Society. J.A.R. was supported by an Alexander von Humboldt postdoctoral fellowship.
Funders:
Funding AgencyGrant Number
NIHGM-27681
American Cancer SocietyPF-10-015-01-CDD
American Cancer SocietyPF-09-262-01-CDD
Alexander von Humboldt FoundationUNSPECIFIED
Issue or Number:20
PubMed Central ID:PMC3195311
Record Number:CaltechAUTHORS:20111122-075248586
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20111122-075248586
Official Citation:Expanding the Repertoire of Natural Product-Inspired Ring Pairs for Molecular Recognition of DNA Katy A. Muzikar, Jordan L. Meier, Daniel A. Gubler, Jevgenij A. Raskatov, and Peter B. Dervan Organic Letters 2011 13 (20), 5612-5615
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:27899
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Nov 2011 16:37
Last Modified:03 Oct 2019 03:27

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