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Related Concept Videos

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.
Biosynthesis of Nucleic Acids01:28

Biosynthesis of Nucleic Acids

Nucleic acid biosynthesis is a fundamental biochemical process that produces the purine and pyrimidine nucleotides essential for DNA and RNA synthesis. This pathway maintains a balanced nucleotide pool, preventing imbalances that could jeopardize genetic integrity and cellular function. Given the crucial role of nucleotides, their synthesis is tightly regulated to ensure proper cellular homeostasis.Purine BiosynthesisThe biosynthesis of purine nucleotides begins with ribose-5-phosphate, a...
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.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...

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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
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Ferrocene-modified pyrimidine nucleosides: synthesis, structure and electrochemistry.

Haifeng Song1, Xiaohong Li, Yitao Long

  • 1Department of Chemistry, University of Saskatchewan, Saskatoon, SK, CanadaS7N 5C9.

Dalton Transactions (Cambridge, England : 2003)
|October 10, 2006
PubMed
Summary

Researchers synthesized ferrocene-modified nucleosides for DNA electron transfer studies. Crystal structures and electrochemical data confirm their potential for investigating redox processes in DNA.

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Electrochemistry

Background:

  • Investigating electron transfer in DNA is crucial for understanding DNA damage and repair mechanisms.
  • Modified nucleosides offer a pathway to probe DNA's electronic properties.
  • Ferrocene (Fc) is a redox-active moiety suitable for electrochemical studies.

Purpose of the Study:

  • To synthesize and characterize ferrocene-modified pyrimidine nucleosides.
  • To explore the potential of these modified nucleosides in studying DNA electron transfer.
  • To determine the structural and electrochemical properties of the synthesized compounds.

Main Methods:

  • Stille coupling reaction for attaching ferrocene to nucleoside bases.
  • Solid-phase synthesis for incorporating modified nucleosides into DNA trinucleotides.
  • Single-crystal X-ray analysis for structural determination.
  • Cyclic voltammetry for electrochemical investigation.

Main Results:

  • Successful synthesis of two ferrocene-modified pyrimidine nucleosides (deoxyuridine and deoxycytidine).
  • Incorporation of Fc-modified uridine into DNA trinucleotides.
  • Determination of crystal structures for detritylated compounds.
  • Observation of reversible redox processes via cyclic voltammetry.

Conclusions:

  • The synthesized ferrocene-modified nucleosides are suitable for investigating electron transfer in DNA.
  • The structural and electrochemical data support their utility in DNA-based studies.
  • These compounds provide a foundation for further research into DNA electrochemistry.