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Related Concept Videos

Nucleic acids02:43

Nucleic acids

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.
DNA and RNA
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, the...
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.
DNA and RNA
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, the...
DNA Base Pairing02:27

DNA Base Pairing

Erwin Chargaff’s rules on DNA equivalence paved the way for the discovery of base pairing in DNA. Chargaff’s rules state that in a double-stranded DNA molecule,
Nucleic Acids02:43

Nucleic Acids

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.
DNA and RNA
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, the...
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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Nucleic Acids and Nucleotides01:20

Nucleic Acids and Nucleotides

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. In...

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Updated: Jul 16, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
15:22

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

Published on: April 3, 2014

Peptide nucleic acid-DNA duplexes containing the universal base 3-nitropyrrole.

B P Zhang1, M Egholm, N Paul

  • 1Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, USA.

Methods (San Diego, Calif.)
|February 22, 2001
PubMed
Summary

This study synthesized a peptide nucleic acid (PNA) monomer with a universal base, 3-nitropyrrole. Results show 3-nitropyrrole pairs with all DNA bases and enhances PNA-DNA duplex thermal stability.

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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
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Self-Assembly of Gamma-Modified Peptide Nucleic Acids into Complex Nanostructures in Organic Solvent Mixtures

Published on: June 26, 2020

Area of Science:

  • Synthetic chemistry
  • Biochemistry
  • Molecular biology

Background:

  • Peptide nucleic acids (PNAs) are DNA mimics with potential therapeutic applications.
  • Developing universal bases that pair with all natural nucleobases is crucial for PNA and DNA applications.
  • 3-nitropyrrole is a promising candidate for a universal base due to its chemical properties.

Purpose of the Study:

  • To synthesize a peptide nucleic acid (PNA) monomer containing the universal base 3-nitropyrrole.
  • To investigate the base-pairing properties and thermal stability of PNA and DNA sequences containing 3-nitropyrrole.
  • To analyze the structural impact of 3-nitropyrrole incorporation into PNA-DNA duplexes.

Main Methods:

  • Chemical synthesis of 3-nitropyrrole-containing PNA monomer.
  • Synthesis of PNA and DNA sequences incorporating the 3-nitropyrrole base.
  • Thermal melting studies (T(m)) to assess duplex stability.
  • Circular dichroism (CD) spectroscopy to analyze structural changes.

Main Results:

  • 3-nitropyrrole was successfully incorporated into a PNA monomer and synthesized into PNA and DNA sequences.
  • 3-nitropyrrole demonstrated indiscriminate pairing with all four natural nucleobases (A, T, C, G) in both PNA and DNA contexts.
  • PNA-DNA duplexes containing 3-nitropyrrole exhibited significantly higher thermal stability (average T(m) = 51.1°C) compared to DNA-DNA duplexes (average T(m) = 39.6°C).
  • Circular dichroism measurements indicated that 3-nitropyrrole incorporation into PNA alters the duplex structure.

Conclusions:

  • 3-nitropyrrole serves as an effective universal base in both PNA and DNA systems.
  • PNAs incorporating 3-nitropyrrole offer enhanced thermal stability for duplex formation compared to DNA.
  • The incorporation of 3-nitropyrrole influences the structural characteristics of nucleic acid duplexes, warranting further investigation.