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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

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Published on: April 3, 2014

A novel polymer supported approach to nucleoside modification.

Suyeal Bae¹, Mahesh K Lakshman

¹The City College and The City University of New York, New York, NY 10031-9198, USA.

The Journal of Organic Chemistry

|April 24, 2008

Summary

New polymer-supported nucleosides (Pol-I and Pol-dI) enable efficient C-6 modification. This solid-phase synthesis approach offers advantages over traditional solution chemistry for creating diverse nucleoside analogues.

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Published on: July 26, 2018

Area of Science:

Organic Chemistry
Medicinal Chemistry
Polymer Chemistry

Background:

Nucleoside modification is crucial for developing novel therapeutics and biochemical tools.
Traditional solution-phase synthesis can be complex and challenging for generating diverse nucleoside libraries.
Solid-phase synthesis offers potential advantages in terms of efficiency and purification.

Purpose of the Study:

To develop and characterize novel polymer-supported inosine derivatives for nucleoside modification.
To investigate the efficiency and scope of solid-phase synthesis for C-6 nucleoside analogues.
To compare the solid-phase approach with traditional solution chemistry methods.

Main Methods:

Synthesis of polymer-linked 1-hydroxybenzotriazole (Pol-HOBt) and subsequent reaction with nucleoside phosphonium salts.
Characterization of polymer-supported nucleosides (Pol-I and Pol-dI) using solid-state Magic Angle Spinning Nuclear Magnetic Resonance (MAS NMR).
Reaction of polymer-supported nucleosides with various nucleophiles (alcohols, phenols, thiols, amines) to achieve C-6 modification and cleavage from the support.

Main Results:

Effective synthesis of polymer-supported O(6)-(benzotriazol-1-yl)inosine derivatives (Pol-I and Pol-dI) was achieved.
Solid-phase synthesis facilitated direct C-6 modification of nucleosides upon exposure to nucleophiles, leading to cleavage from the support.
Comparison with solution chemistry highlighted differences and advantages of the polymer-supported approach for nucleoside modification.

Conclusions:

The study presents the first application of polymer-supported technology for nucleoside modification.
The developed polymer-supported nucleosides are suitable for diversity-oriented synthesis.
This solid-phase methodology provides a convenient and efficient route to C-6 modified nucleoside analogues.