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Chemical Triphosphorylation of Oligonucleotides

Chemical Triphosphorylation of Oligonucleotides

Published on: June 2, 2022

Chemoselective Dimerization of Phosphates.

Alexandre Hofer, Elia Marques, Nicole Kieliger

¹Plant Biochemistry & Physiology Laboratory, Department of Botany and Plant Biology, University of Geneva , Quai E. Ansermet 30, 1211 Geneva, Switzerland.

Organic Letters

|June 17, 2016

Summary

This summary is machine-generated.

This study introduces a new phosphordiamidite method for synthesizing oligophosphate conjugates. This approach enables the creation of various nucleotide chains, including thiamine-modified compounds for enzyme inhibition studies.

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Area of Science:

Organic Chemistry
Biochemistry
Nucleotide Chemistry

Background:

Oligophosphate conjugates are crucial in biological systems.
Efficient synthesis methods are needed for studying nucleotide function.
Thiamine-modified nucleotides have potential therapeutic applications.

Purpose of the Study:

To describe a novel methodology for synthesizing oligophosphate conjugates.
To enable the preparation of diverse C2-symmetric and unsymmetric nucleotide structures.
To investigate the inhibitory effects of thiaminylated nucleotides on specific enzymes.

Main Methods:

Synthesis of oligophosphate conjugates using phosphordiamidites.
Preparation of C2-symmetric dinucleoside tri-, penta-, and heptaphosphates.
Synthesis of unsymmetric compounds like thiamine adenosine triphosphate and thiamine cytidine triphosphate.

Main Results:

A straightforward and versatile phosphordiamidite strategy was established.
Successfully synthesized various symmetrical and unsymmetrical oligophosphate conjugates.
Thiaminylated nucleotides demonstrated inhibitory activity against adenosine diphosphate ribosyltransferases.

Conclusions:

The developed phosphordiamidite methodology offers an efficient route to complex oligophosphates.
This synthesis strategy is valuable for preparing thiamine-modified nucleotides.
The findings support the potential of thiaminylated nucleotides as inhibitors for ADP-ribosyltransferases.