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Biosynthesis of Nucleic Acids

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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...
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Base-Catalyzed Ring-Opening of Epoxides02:26

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Pyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions.

Elfie S Cavalli1, Thomas Mies1, Henry S Rzepa1

  • 1Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London, 82 Wood Lane, London W12 0BZ, England.

Organic Letters
|November 4, 2022
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Summary
This summary is machine-generated.

This study presents an efficient two-step synthesis for pyrimidine nucleosides and their derivatives. The method utilizes Meldrum

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Nucleoside Chemistry

Background:

  • Pyrimidine nucleosides are vital components in nucleic acids and have diverse pharmaceutical applications.
  • Efficient synthetic routes are crucial for accessing novel nucleoside analogs with potential therapeutic value.

Purpose of the Study:

  • To develop a streamlined, two-step procedure for synthesizing pyrimidine nucleosides.
  • To explore the conversion of these nucleosides into various C-5 derivatives.

Main Methods:

  • Preparation of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives from β-anomeric isonitriles and Meldrum's acid derivatives.
  • Transacylation reactions with isocyanates to yield uridine-5-carboxylic acid derivatives and related nucleosides.
  • Bromo-decarboxylation using N-bromosuccinimide to generate diverse C-5 substituted nucleosides.

Main Results:

  • An efficient two-step synthesis was established for pyrimidine nucleosides.
  • Uridine-5-carboxylic acid derivatives and related nucleosides were successfully synthesized.
  • A range of C-5 substituted nucleosides were obtained via bromo-decarboxylation.

Conclusions:

  • The presented two-step method offers an efficient route to pyrimidine nucleosides.
  • This methodology allows for the facile synthesis of diverse C-5 functionalized nucleoside analogs.
  • The developed procedure is valuable for medicinal chemistry and drug discovery efforts.