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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Phosphodiester Linkages01:01

Phosphodiester Linkages

Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Generation of Straight or Branched Actin Filaments01:14

Generation of Straight or Branched Actin Filaments

The straight or branched structure formation of actin filaments is controlled by nucleating proteins such as the formins and Arp2/3 complex. Formin-mediated assembly results in straight filaments, whereas Arp2/3 protein complex-mediated assembly results in branched actin filaments.
Arp2/3 Complex
Arp2/3 complex is a seven-subunit complex consisting of two proteins similar to actin- Arp2 and Arp3, and five other subunits that help keep Arp2 and Arp3 inactive. When required, the complex is...
Cooperative Allosteric Transitions01:58

Cooperative Allosteric Transitions

Cooperative allosteric transitions can occur in multimeric proteins, where each subunit of the protein has its own ligand-binding site. When a ligand binds to any of these subunits, it triggers a conformational change that affects the binding sites in the other subunits; this can change the affinity of the other sites for their respective ligands. The ability of the protein to change the shape of its binding site is attributed to the presence of a mix of flexible and stable segments in the...
Cooperative Allosteric Transitions01:58

Cooperative Allosteric Transitions

Cooperative allosteric transitions can occur in multimeric proteins, where each subunit of the protein has its own ligand-binding site. When a ligand binds to any of these subunits, it triggers a conformational change that affects the binding sites in the other subunits; this can change the affinity of the other sites for their respective ligands. The ability of the protein to change the shape of its binding site is attributed to the presence of a mix of flexible and stable segments in the...

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Related Experiment Video

Updated: Jun 8, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Unexpectedly stable artificial duplex from flexible acyclic threoninol.

Hiroyuki Asanuma1, Takasuke Toda, Keiji Murayama

  • 1Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. asanuma@mol.nagoya-u.ac.jp

Journal of the American Chemical Society
|October 5, 2010
PubMed
Summary

A novel acyclic threoninol nucleic acid (aTNA) forms exceptionally stable duplexes, surpassing DNA and RNA stability. This discovery offers new possibilities for nucleic acid research and applications.

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Published on: January 19, 2016

Area of Science:

  • Synthetic organic chemistry
  • Nucleic acid chemistry
  • Biochemistry

Background:

  • Development of novel nucleic acid analogs is crucial for expanding the toolkit of molecular biology.
  • Understanding structure-stability relationships in nucleic acid duplexes informs therapeutic and diagnostic applications.

Purpose of the Study:

  • To synthesize and characterize a new foldamer, acyclic threoninol nucleic acid (aTNA).
  • To evaluate the duplex stability of aTNA compared to natural DNA and RNA.

Main Methods:

  • Synthesis of aTNA by tethering genetic nucleobases (A, G, C, T) to d-threoninol building blocks.
  • Incorporation of aTNA building blocks into a phosphodiester-linked scaffold.
  • Formation and stability assessment of aTNA/aTNA antiparallel duplexes.

Main Results:

  • Successful synthesis of the acyclic threoninol nucleic acid (aTNA) foldamer.
  • aTNA oligomers form exceptionally stable duplexes with complementary strands in an antiparallel orientation.
  • The stability of aTNA duplexes significantly exceeds that of corresponding DNA or RNA duplexes.
  • Single-stranded aTNA exhibits flexibility, lacking a preorganized structure.

Conclusions:

  • Acyclic threoninol nucleic acid (aTNA) represents a promising new class of nucleic acid analogs.
  • The remarkable duplex stability of aTNA opens avenues for novel applications in biotechnology and medicine.
  • Further research into aTNA structure-function relationships is warranted.