CaltechAUTHORS
  A Caltech Library Service

Hairpin Peptide Motif. A New Class of Oligopeptides for Sequence-Specific Recognition in the Minor Groove of Double-Helical DNA

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

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20160510-131559184

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00097a004DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00097a004PublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
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.
Funders:
Funding AgencyGrant Number
NIHGM-27681
Ralph M. Parsons FoundationUNSPECIFIED
NIH Predoctoral FellowshipUNSPECIFIED
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

Repository Staff Only: item control page