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Influence of β-Alanine on Hairpin Polyamide Orientation in the DNA Minor Groove

Rucker, Victor C. and Melander, Christian and Dervan, Peter B. (2003) Influence of β-Alanine on Hairpin Polyamide Orientation in the DNA Minor Groove. Helvetica Chimica Acta, 86 (6). pp. 1839-1851. ISSN 0018-019X. doi:10.1002/hlca.200390148. https://resolver.caltech.edu/CaltechAUTHORS:20160510-075438695

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Abstract

Antiparallel polyamides containing 1H-pyrrole, 1H-imidazole, and 3-hydroxy-1H-pyrrole amino acids display a preference for minor-groove binding oriented N-C with respect to the 5′-3′ direction of the DNA helix. We find that replacement of a central Py/Py pair with a β/β pair within a ten-ring hairpin relaxes the orientation preference and, for some DNA sequences, causes the polyamide to prefer the opposite C-N orientation. Substitution of the achiral γ-aminobutanoic acid (γ) with either (R)(or S)-2-(acetylamino)-4-aminobutanoic acid moderates the orientation preference of the 2-β-2-hairpin.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/hlca.200390148DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/hlca.200390148/abstractPublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2003 Schweizerische Chemische Gesellschaft, Switzerland. Received April 14, 2003. Article first published online: 10 JUL 2003. We are grateful to the National Institutes of Health for research support (GM-27681), for a biology training grant to V. C. R. (GM19789-02), and for a postdoctoral fellowship to C. M. (GM19789-02). We also thank G. M. Hathaway for MALDI-TOF mass spectrometry.
Funders:
Funding AgencyGrant Number
NIHGM-27681
NIH Postdoctoral FellowshipGM19789-02
Issue or Number:6
DOI:10.1002/hlca.200390148
Record Number:CaltechAUTHORS:20160510-075438695
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160510-075438695
Official Citation:Rucker, Victor C., Melander, C. and Dervan, Peter B. (2003), Influence of β-Alanine on Hairpin Polyamide Orientation in the DNA Minor Groove. HCA, 86: 1839–1851. doi: 10.1002/hlca.200390148
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66795
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:10 May 2016 19:45
Last Modified:11 Nov 2021 00:03

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