Cited by 286DNA and Nucleic Acid ChemistryAdvanced biosensing and bioanalysis techniquesRNA and protein synthesis mechanisms

A Simple γ-Backbone Modification Preorganizes Peptide Nucleic Acid into a Helical Structure

Dragulescu-Andrasi, Anca, Rapireddy, Srinivas, Frezza, Brian M., Gayathri, Chakicherla, Gil, Roberto R., Ly, Danith H.·2006·Journal of the American Chemical Society

Abstract

Peptide nucleic acid (PNA) is a synthetic analogue of DNA and RNA, developed more than a decade ago in which the naturally occurring sugar phosphate backbone has been replaced by the N-(2-aminoethyl) glycine units. Unlike DNA or RNA in the unhybridized state (single strand) which can adopt a helical structure through base-stacking, although highly flexible, PNA does not have a well-defined conformational folding in solution. Herein, we show that a simple backbone modification at the gamma-position of the N-(2-aminoethyl) glycine unit can transform a randomly folded PNA into a helical structure. Spectroscopic studies showed that helical induction occurs in the C- to N-terminal direction and is sterically driven. This finding has important implication not only on the future design of nucleic acid mimics but also on the design of novel materials, where molecular organization and efficient electronic coupling are desired.

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Crossref · 10.1021/ja0625576

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  • The primer can be engineered to discriminate DNA's chirality using gamma-modified PNA.

    “The achiral nature of PNA does not discriminate between d- or l-DNA; however, the primer can be engineered to discriminate DNA’s chirality using gamma-modified PNA42 which imparts chirality to the PNA primers.”
  • The primers used contain chiral PNA residues that hybridize exclusively to d-DNA.

    “However, the primers that were used contain chiral PNA residues22,41 that hybridize exclusively to d-DNA.42,43”

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Authors
Dragulescu-Andrasi, A., Rapireddy, S., Frezza, B. M., Gayathri, C., Gil, R. R., & Ly, D. H.
Affiliations
  • Contribution from the Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania 15213
  • Carnegie Mellon University (US)
Venue
Journal of the American Chemical Society
Published
2006-07-19
Volume
128
Issue
31
Pages
10258-10267
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
OpenAlex
W2040054282
Cited by
286
References
38
Citations by year
2026: 17 · 2025: 12 · 2024: 16 · 2023: 15 · 2022: 18 · 2021: 18 · 2020: 23 · 2019: 16 · 2018: 18 · 2017: 18 · 2016: 16 · 2015: 15 · 2014: 11 · 2013: 12 · 2012: 18
FWCI
2.84
Type
journal article
Language
en
Open access
closed
Locations
  • Journal of the American Chemical Society (publishedVersion)
  • PubMed (publishedVersion)
Funders
Division of Chemistry
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Advanced biosensing and bioanalysis techniques
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
Keywords
peptide nucleic acid, helical conformation, backbone modification, steric effects, nucleic acid mimics, electronic coupling
MeSH terms
Circular Dichroism, Models, Molecular, Nucleic Acid Conformation, Temperature, Dimerization, Nuclear Magnetic Resonance, Biomolecular, Peptide Nucleic Acids

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