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High-Density DNA and RNA microarrays - Photolithographic Synthesis, Hybridization and Preparation of Large Nucleic Acid Libraries

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Building Boron Heterocycles into DNA-Encoded Libraries.

Pinwen Cai¹, Lukas A Schneider¹, Cedric Stress¹

¹Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel 4056, Switzerland.

Organic Letters

|November 1, 2021

Summary

Researchers developed a new DNA-encoded library (DEL) reaction for synthesizing unique boron-containing pyridazine heterocycles. This method enables reversible covalent interactions, expanding DEL capabilities for drug discovery.

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Area of Science:

Medicinal Chemistry
Organic Synthesis
Chemical Biology

Background:

DNA-encoded library (DEL) technology is a powerful method for drug discovery, enabling the screening of vast chemical libraries.
DEL synthesis requires reactions that are compatible with combinatorial chemistry and preserve DNA tag information.
Existing DEL methodologies lack efficient ways to incorporate specific chemical functionalities for targeted molecular interactions.

Purpose of the Study:

To develop a novel DEL-compatible reaction for synthesizing a unique class of boron-containing pyridazine heterocycles.
To engineer a heterocycle capable of reversible covalent interactions, specifically with alcohols, for enhanced DEL applications.
To expand the chemical space and interaction modalities available within DNA-encoded libraries.

Main Methods:

A novel synthetic route was designed and optimized for the construction of boron-containing pyridazine heterocycles.
The reaction conditions were rigorously tested for compatibility with split-and-pool combinatorial synthesis and DNA integrity.
The synthesized heterocycles were characterized for their chemical properties and interaction capabilities, particularly with alcohols.

Main Results:

A robust and DEL-compatible reaction for assembling boron-containing pyridazine heterocycles was successfully established.
The synthesized heterocycles demonstrated unique reversible covalent interactions with alcohols.
This represents the first deliberate engineering of reversible covalent alcohol interactions within DELs.

Conclusions:

The new reaction provides a valuable tool for expanding the diversity of DNA-encoded libraries.
The engineered heterocycle's ability to form reversible covalent bonds with alcohols opens new avenues for designing targeted therapeutics.
This advancement enhances the utility of DEL technology in accelerating drug discovery and chemical biology research.