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Controlling binding orientation in hairpin polyamide DNA complexes

Hawkins, Cheryl A. and Peláez de Clairac, Rafael and Dominey, Raymond N. and Baird, Eldon E. and White, Sarah and Dervan, Peter B. and Wemmer, David E. (2000) Controlling binding orientation in hairpin polyamide DNA complexes. Journal of the American Chemical Society, 122 (22). pp. 5235-5243. ISSN 0002-7863. doi:10.1021/ja0001198.

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The effects of N-terminal acetylation and C-terminal tail structure on the orientation of binding of imidazole/pyrrole polyamide DNA ligands has been investigated. We find that N-terminal acetylation leads to an intramolecular steric clash for hairpin ligands bound in the minor groove, promoting a rotation of the spatially close C-terminal pyrrole ring. This in turn leads to loss of contacts between the tail and the groove, removing the preference for 5‘-to-3‘ orientational binding typical of this class of ligand. Similarly, introduction of a glycine linker into the tail leads to a direct steric clash with the groove, again promoting rotation of the attached ligand ring. The effects of acetylation and a glycine in the tail are additive. The implications for the design of sequence-specific ligands are discussed.

Item Type:Article
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Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2000 by the American Chemical Society. Received January 10, 2000. Publication Date (Web): May 18, 2000.
Issue or Number:22
Record Number:CaltechAUTHORS:20160510-084721396
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Official Citation:Controlling Binding Orientation in Hairpin Polyamide DNA Complexes Cheryl A. Hawkins, Rafael Peláez de Clairac, Raymond N. Dominey, Eldon E. Baird, Sarah White, Peter B. Dervan,and David E. Wemmer Journal of the American Chemical Society 2000 122 (22), 5235-5243 DOI: 10.1021/ja0001198
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66838
Deposited By: Victoria Brennan
Deposited On:10 May 2016 19:17
Last Modified:11 Nov 2021 00:04

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