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DNA-Compatible Copper/TEMPO Oxidation for DNA-Encoded Libraries.
Justice L Merrifield1, Edward B Pimentel1, Trenton M Peters-Clarke1,2
1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Bioconjugate Chemistry
|August 4, 2023
Summary
Researchers developed a DNA-compatible method for oxidizing alcohols to aldehydes using a copper/TEMPO catalyst. This advancement aids DNA-encoded library construction and diversification.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Biotechnology
Background:
- Aldehydes are crucial building blocks in DNA-encoded library (DEL) construction.
- Developing DNA-compatible methods for alcohol oxidation to aldehydes is a significant challenge in DEL chemistry.
Purpose of the Study:
- To develop a solution-phase, DNA-compatible method for oxidizing DNA-linked primary alcohols to aldehydes.
- To demonstrate the utility of the resulting aldehydes for library diversification.
Main Methods:
- Utilized a copper/TEMPO catalyst system for oxidation.
- Performed reactions under semiaqueous, room-temperature conditions.
- Verified DNA compatibility using mass spectrometry, qPCR, Sanger sequencing, and ligation assays.
Main Results:
- Achieved high yields in the oxidation of benzylic, heterobenzylic, and allylic alcohols.
- Confirmed the integrity of DNA post-reaction through multiple analytical techniques.
- Demonstrated successful subsequent transformations of the generated aldehydes.
Conclusions:
- The developed copper/TEMPO catalyzed oxidation is a robust and DNA-compatible method for generating aldehydes.
- This method significantly advances DEL construction by enabling efficient and versatile library diversification.
