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Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
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Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Enabling Multiple Conjugation to Oligonucleotides Using "Click Cycles".

Martina Jezowska1, Dmytro Honcharenko1, Alice Ghidini1

  • 1Department of Biosciences and Nutrition, Karolinska Institute, Novum , SE-14183 Huddinge, Sweden.

Bioconjugate Chemistry
|October 21, 2016
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Summary
This summary is machine-generated.

A new H-phosphonate alkyne linker enables efficient synthesis of multiply functionalized oligonucleotides (ONs). This method allows stepwise attachment of diverse molecules like peptides and fluorescent labels to ONs via click chemistry.

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Area of Science:

  • Oligonucleotide Synthesis
  • Chemical Biology
  • Bioconjugation Chemistry

Background:

  • Multiply functionalized oligonucleotides (ONs) are crucial for advanced applications in diagnostics and therapeutics.
  • Existing methods for ON functionalization often face limitations in efficiency, versatility, and stepwise control.

Purpose of the Study:

  • To develop an efficient and versatile method for the synthesis of multiply functionalized oligonucleotides (ONs).
  • To enable the stepwise conjugation of diverse active entities to the 5'-terminus of ONs.

Main Methods:

  • Development of a novel H-phosphonate alkyne-based linker for multiple functionalization (LMF).
  • Post-synthetic attachment of LMF to the 5'-terminus of ONs using H-phosphonate chemistry.
  • Stepwise conjugation of azido-containing molecules via [3+2] copper(I) catalyzed cycloaddition (click chemistry).

Main Results:

  • Successful synthesis of oligonucleotide conjugates with up to three different attached entities.
  • Demonstrated high conversion rates in each step of the sequential solid-phase synthesis.
  • Synthesized conjugates incorporating diverse molecules including sugars, peptides, fluorescent labels, and m3G-Caps, showcasing method versatility.

Conclusions:

  • The developed H-phosphonate alkyne-based linker strategy provides an efficient and versatile platform for synthesizing multiply functionalized oligonucleotides.
  • The stepwise click chemistry approach allows for precise control over the conjugation of various functional moieties, expanding the utility of ONs.