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Related Concept Videos

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...

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Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
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Triplex glue by synthesizing conjugated flexible intercalators.

Erik B Pedersen1, Amany M A Osman, Daniel Globisch

  • 1Nucleic Acid Center, Institute of Physics and Chemistry, University of Southern Denmark, DK-5230 Odense M, Denmark. ebp@ifk.sdu.dk

Nucleic Acids Symposium Series (2004)
|September 9, 2008
PubMed
Summary

Conjugated intercalators enhance DNA triplex stability and disrupt G-rich oligonucleotide self-association. This approach enables the assembly of more stable alternate strand triplexes, overcoming challenges in TFO connectivity.

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Area of Science:

  • Molecular Biology
  • Biochemistry
  • Organic Chemistry

Background:

  • DNA triplexes and quadruplexes are crucial nucleic acid structures.
  • G-rich oligonucleotides form stable quadruplexes under physiological conditions.
  • Modulating DNA structure stability is key for therapeutic applications.

Purpose of the Study:

  • To investigate the impact of conjugated intercalators on DNA triplex stability.
  • To explore the effect of conjugated intercalators on G-rich oligonucleotide quadruplexes.
  • To assess the utility of intercalators in assembling alternate strand triplexes.

Main Methods:

  • Synthesis and characterization of various conjugated intercalators.
  • Assays to measure thermal stability of DNA triplexes.
  • Studies on the effect of intercalators on G-rich oligonucleotide self-association.

Main Results:

  • Bulge insertions of conjugated intercalators significantly increase DNA triplex stability.
  • Conjugated intercalators disrupt G-rich oligonucleotide quadruplex formation.
  • Intercalators facilitate the assembly of stable alternate strand triplexes with improved thermal stability.

Conclusions:

  • Conjugated intercalators are effective agents for stabilizing DNA triplexes.
  • This strategy offers a novel method for controlling DNA secondary structures.
  • The intercalator approach provides a versatile tool for constructing stable, functional DNA architectures.