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Related Concept Videos

Peptide Bonds02:43

Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Nucleic acids02:43

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Nucleic acids are the most important macromolecules for the continuity of life. They carry the cell's genetic blueprint and carry instructions for its functioning.
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The two main types of nucleic acids are deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). DNA is the genetic material in all living organisms, ranging from single-celled bacteria to multicellular mammals. It is in the nucleus of eukaryotes and in the organelles, chloroplasts, and mitochondria. In prokaryotes,...
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Nucleic Acids02:43

Nucleic Acids

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Nucleic acids are the most important macromolecules for the continuity of life. They carry the cell's genetic blueprint and carry instructions for its functioning.
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Nucleic Acids and Nucleotides01:20

Nucleic Acids and Nucleotides

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Nucleic acids are the most important macromolecules for the continuity of life. They carry the cell's genetic blueprint and have instructions for its functioning. The two main types of nucleic acids are deoxyribonucleic acid (DNA) and ribonucleic acid (RNA).
Deoxyribonucleic Acid (DNA)
DNA is the genetic material in all living organisms, ranging from single-celled bacteria to multicellular mammals. It is in the nucleus of eukaryotes and the organelles such as chloroplasts and mitochondria....
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Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

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Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Related Experiment Video

Updated: May 5, 2026

Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids
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Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids

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Cyclopentane peptide nucleic acids.

Ethan A Englund1, Ning Zhang, Daniel H Appella

  • 1Section on Synthetic Bioactive Molecules, Laboratory of Bioorganic Chemistry, NIDDK, NIH, DHHS, Bethesda, MD, USA.

Methods in Molecular Biology (Clifton, N.J.)
|December 4, 2013
PubMed
Summary
This summary is machine-generated.

Adding a cyclopentane ring to peptide nucleic acid backbones significantly enhances their binding to DNA and RNA. This modification offers a versatile strategy for improving nucleic acid binding across various base types.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Molecular Biology

Background:

  • Peptide nucleic acids (PNAs) are synthetic DNA mimics with high binding affinity.
  • Modifications to the PNA backbone can further enhance stability and binding characteristics.
  • Improving PNA binding is crucial for applications in diagnostics and therapeutics.

Purpose of the Study:

  • To investigate the effect of incorporating a cyclopentane ring into the PNA backbone.
  • To determine if this modification enhances binding affinity to complementary nucleic acid sequences.
  • To assess the general applicability of this modification for PNA-based applications.

Main Methods:

  • Synthesis of modified peptide nucleic acid monomers containing a cyclopentane ring.
  • Preparation of PNA oligomers with the modified backbone.
  • Hybridization studies with complementary DNA and RNA sequences.
  • Analysis of binding affinity using biophysical techniques.

Main Results:

  • Incorporation of the cyclopentane ring into the PNA backbone demonstrably increased binding affinity.
  • The enhanced binding was observed for PNA sequences targeting both purine and pyrimidine bases.
  • This modification proved to be a general method for improving PNA-nucleic acid interactions.

Conclusions:

  • Cyclopentane ring incorporation is an effective strategy for enhancing PNA binding affinity.
  • This approach offers a versatile tool for designing improved PNA-based molecules.
  • The findings support the development of novel PNA therapeutics and diagnostics.