Mrksich, Milan and Parks, Michell E. and Dervan, Peter B. (1994) Hairpin Peptide Motif. A New Class of Oligopeptides for Sequence-Specific Recognition in the Minor Groove of Double-Helical DNA. Journal of the American Chemical Society, 116 (18). pp. 7983-7988. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20160510-131559184
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Abstract
Peptides which bind in the minor groove of DNA as antiparallel side-by-side dimers can be linked head-to-tail to afford a new class of hairpin oligopeptides with enhanced sequence specificity for DNA. Four hexapeptides were synthesized wherein the terminal amine and carboxyl groups of tris(N-methylpyrrolecarboxamide) (P3) and N-methylimidazole-2-carboxamide-netropsin (2-ImN), respectively, have been connected with glycine (Gly), β-alanine (βAla), 4-aminobutyric acid (GABA), and 5-aminovaleric acid (Ava) amino acids. The hexapeptide 2-ImN-GABA-P3 binds 5'-TGTTA-3' sites with a binding affinity of 7.6 X 10^7 M^(-1) (10 mM Tris·HCl, 10 mM KCl, 10 mM MgCl_2, and 5 mM CaCl_2 at pH 7.0 and 22 °C). The general and efficient synthetic methodology-for preparation of head-to-tail linked peptides should allow the design of a new class of hairpin peptides for specific recognition of many different sequences in the minor groove of DNA.
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Additional Information: | © 1994 American Chemical Society. Received March 7, 1994. We are grateful to the National Institutes of Health (Grant GM-27681) for research support, the Ralph M. Parsons Foundation for a Graduate Fellowship to M.M., and a National Institutes of Health Research Service Award to M.E.P. | |||||||||
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Issue or Number: | 18 | |||||||||
Record Number: | CaltechAUTHORS:20160510-131559184 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20160510-131559184 | |||||||||
Official Citation: | Hairpin Peptide Motif. A New Class of Oligopeptides for Sequence-Specific Recognition in the Minor Groove of Double-Helical DNA Milan Mrksich, Michelle E. Parks, and Peter B. Dervan Journal of the American Chemical Society 1994 116 (18), 7983-7988 DOI: 10.1021/ja00097a004 | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 66908 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Victoria Brennan | |||||||||
Deposited On: | 19 May 2016 16:36 | |||||||||
Last Modified: | 26 Nov 2019 11:15 |
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