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Solvent-Assisted Mechanochemical Synthesis of a Nucleotide Dimer.

Christopher Johnston1, Marie E Migaud2

  • 1School of Pharmacy, Queen's University, Belfast, United Kingdom.

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|April 21, 2022
PubMed
Summary

This study presents a solvent-assisted mechanochemical method for synthesizing nucleotide dimers, offering a simpler, more stable alternative to traditional solution-phase chemistry. This approach is expected to be broadly applicable to various nucleoside monomers.

Keywords:
DNAdinucleotidemechanochemistryoligonucleotidesphosphoramidite

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Biochemistry

Background:

  • Traditional solution-phase synthesis of nucleotide dimers can be challenging due to solubility issues and hydrolytic instability.
  • Mechanochemistry offers a promising alternative for chemical synthesis, potentially overcoming limitations of conventional methods.

Purpose of the Study:

  • To develop and detail a protocol for the solvent-assisted mechanochemical synthesis of nucleotide dimers.
  • To demonstrate the advantages of mechanochemistry in nucleotide synthesis, including simplicity and improved stability.

Main Methods:

  • Solvent-assisted mechanochemical synthesis of a dinucleoside phosphite using the phosphoramidite method.
  • Oxidation of the dinucleoside phosphite to the dinucleotide under mechanochemical conditions.
  • Purification of the dinucleotide via column chromatography.

Main Results:

  • Successful synthesis of a nucleotide dimer using solvent-assisted mechanochemistry.
  • Demonstration of mechanochemical conditions' efficacy, distinct from solvent effects.
  • Preparation of acidic salts for phosphoramidite couplings.

Conclusions:

  • Solvent-assisted mechanochemistry provides an efficient and advantageous method for nucleotide dimer synthesis.
  • The protocol is anticipated to be widely applicable to a range of nucleoside and ribonucleoside monomers.
  • Mechanochemical synthesis offers improved hydrolytic stability and eliminates the need for solubilizing poorly soluble compounds.