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Biosynthesis of Nucleic Acids01:28

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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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Nucleic Acid Structure01:25

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The pentose sugar in DNA is deoxyribose, while in RNA the pentose sugar is ribose. The difference between the sugars is the presence of the hydroxyl group on the ribose's second carbon and a hydrogen on the deoxyribose's second carbon. The phosphate residue attaches to the hydroxyl group of the 5′ carbon of one sugar and the hydroxyl group of the 3′ carbon of the sugar of the next nucleotide, which forms  a 5′ to 3′ phosphodiester linkage.
DNA Structure
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Structures of Carboxylic Acid Derivatives01:28

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
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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)
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Boronic acid-modified nucleoside - synthesis and structural characterisation in the solid state.

Tabea Lenz1, Marian Hebenbrock1

  • 1Institute of Inorganic and Analytical Chemistry, University of Münster, Münster, Germany.

Nucleosides, Nucleotides & Nucleic Acids
|June 28, 2025
PubMed
Summary
This summary is machine-generated.

Researchers elucidated the first structure of a boronic acid-modified nucleoside. Its minor structural influence suggests potential as a functionalized thymidine analogue in deoxyoligonucleotides.

Keywords:
Nucleic acid’s modificationboronic acidsingle crystal X-ray diffraction

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Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism
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Area of Science:

  • Organic Chemistry
  • Structural Biology
  • Nucleoside Chemistry

Background:

  • Nucleosides are fundamental building blocks of DNA and RNA.
  • Modification of nucleosides can lead to novel therapeutic agents and biochemical tools.
  • Boronic acids are versatile functional groups with unique chemical properties.

Purpose of the Study:

  • To determine the crystal structure of a novel boronic acid-modified nucleoside.
  • To investigate the synthetic accessibility of boronic acid-modified nucleosides.
  • To assess the structural impact of the boronic acid modification on nucleoside geometry and its potential applications.

Main Methods:

  • Single-crystal X-ray diffraction was used to elucidate the molecular structure.
  • Synthesis of the boronic acid-modified nucleoside was performed under alternative reaction conditions.
  • Comparison of structural data with a tert-butyldimethylsilyl-protected derivative and natural nucleosides.

Main Results:

  • The first crystal structure of a boronic acid-modified nucleoside was determined.
  • The sugar pucker showed slight deviation, but nucleobase geometry remained similar to natural nucleosides.
  • Inter- and intramolecular hydrogen bonds involving the boronic acid residue facilitated the formation of supramolecular zigzag chains.

Conclusions:

  • The boronic acid modification has a minor influence on the overall nucleoside geometry.
  • The elucidated structure supports the potential of this modified nucleoside as a functionalized thymidine analogue.
  • This finding favors its utility in the development of deoxyoligonucleotides for various applications.