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Optimization of the hairpin polyamide design for recognition of the minor groove of DNA

Parks, Michelle E. and Baird, Eldon E. and Dervan, Peter B. (1996) Optimization of the hairpin polyamide design for recognition of the minor groove of DNA. Journal of the American Chemical Society, 118 (26). pp. 6147-6152. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20160510-103524820

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Abstract

In order to optimize the hairpin design for ligands which bind the minor groove of DNA, a series of four pyrrole−imidazole polyamides substituted at the C-terminus with aliphatic amino acids have been prepared using solid phase synthetic methodology. Addition of a C-terminal β-alanine residue is found to enhance both the DNA binding affinity and sequence specificity, while addition of a C-terminal glycine residue is found to reduce DNA binding affinity and sequence specificity. These effects are modulated by the addition of an N-terminal acetyl group. Insertion of a C-terminal aliphatic amino acid residue makes the hairpin polyamide motif compatible with solid phase synthetic methods, allowing the rapid design of new polyamides for high-affinity specific recognition of a broad sequence repertoire in the minor groove of DNA.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja960721rDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja960721rPublisherArticle
Additional Information:© 1996 American Chemical Society. Received March 5, 1996. Publication Date (Web): July 3, 1996. Abstract published in Advance ACS Abstracts, June 15, 1996. We are grateful to the National Institutes of Health (GM-27681) for grant support and a research service award to M.E.P., and to the Howard Hughes Medical Institute for a predoctoral fellowship to E.E.B.
Funders:
Funding AgencyGrant Number
NIHGM-27681
NIH Predoctoral FellowshipUNSPECIFIED
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Record Number:CaltechAUTHORS:20160510-103524820
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160510-103524820
Official Citation:Optimization of the Hairpin Polyamide Design for Recognition of the Minor Groove of DNA Michelle E. Parks, Eldon E. Baird, and Peter B. Dervan Journal of the American Chemical Society 1996 118 (26), 6147-6152 DOI: 10.1021/ja960721r
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66888
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:18 May 2016 21:14
Last Modified:18 May 2016 21:14

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