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Related Concept Videos

Nucleic Acids and Nucleotides01:20

Nucleic Acids and Nucleotides

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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).
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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.
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RNA Structure01:23

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Nucleic acids are the most important macromolecules for the continuity of life. They carry the cell's genetic blueprint and carry instructions for its functioning.
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Phosphodiester Linkages01:01

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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.
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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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Convertible and Constrained Nucleotides: The 2'-Deoxyribose 5'-C-Functionalization Approach, a French Touch.

Crystalle Chardet1, Corinne Payrastre1, Béatrice Gerland1

  • 1Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, UMR CNRS 5068, Université Paul Sabatier, 118 Route de Narbonne, CEDEX 9, 31062 Toulouse, France.

Molecules (Basel, Switzerland)
|October 13, 2021
PubMed
Summary

Researchers modified the 5' carbon of nucleotides to create convertible (CvN) and constrained (CNA) oligonucleotides. These modified nucleic acids offer enhanced stability and functionalization for biological applications.

Keywords:
constrained nucleic acidsconvertible and constrained nucleic acidsconvertible approacholigonucleotides conjugation

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Area of Science:

  • Chemical Biology
  • Nucleic Acid Chemistry
  • Biotechnology

Background:

  • Oligonucleotides are key molecules in biology and biotechnology.
  • Modifying oligonucleotide properties requires new chemical strategies.
  • Existing methods often struggle to balance functionality, affinity, and structural integrity.

Purpose of the Study:

  • To review a novel approach for modifying oligonucleotides at the 5'-C position.
  • To demonstrate the creation of convertible (CvN) and conformationally constrained (CNA) nucleotides.
  • To explore the applications of these modified oligonucleotides in functionalization and stabilization.

Main Methods:

  • Synthesis of 5'-C modified nucleosides, including bromo or propargyl convertible nucleotides (CvN).
  • Stereocontrolled linkage of the 5'-carbon to the phosphate moiety to create conformationally constrained nucleotides (CNA).
  • Combination of both approaches to yield constrained and convertible nucleotides (C2NA).

Main Results:

  • CvN nucleotides were synthesized in pure diastereoisomeric forms, enabling nucleophilic displacement and CuAAC conjugation.
  • CNA nucleotides allowed precise control over sugar/phosphate backbone torsional angles.
  • Modulated nucleic acid structures exhibited significant stabilization of duplex and hairpin formations.

Conclusions:

  • Modification of the 5'-C position is a versatile strategy for oligonucleotide engineering.
  • CvN and CNA nucleotides provide powerful tools for introducing chemical handles and controlling nucleic acid conformation.
  • The combined C2NA approach offers unique capabilities for functionalizing and stabilizing nucleic acids for diverse applications.