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Related Concept Videos

The DNA Helix01:16

The DNA Helix

Overview
The DNA Helix01:16

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Covalently Linked Protein Regulators02:04

Covalently Linked Protein Regulators

Proteins can undergo many types of post-translational modifications, often in response to changes in their environment. These modifications play an important role in the function and stability of these proteins. Covalently linked molecules include functional groups, such as methyl, acetyl, and phosphate groups, and also small proteins, such as ubiquitin. There are around 200 different types of covalent regulators that have been identified.
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Labeling DNA Probes03:31

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Spontaneous mutations arise infrequently during DNA replication due to errors in the process. A key factor behind these errors is tautomeric shifts in nitrogenous bases, where bases transition from keto to enol forms or amino to imino forms. This shift can alter base-pairing rules, leading to mutations. Additionally, reactive oxygen species (ROS) arising from aerobic metabolism can damage DNA, resulting in depurination (loss of a purine base) or depyrimidination (loss of a pyrimidine base).

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Light-induced β-hydroxy sulfone synthesis in DNA-encoded libraries.

Lijun Xue1, Jiaqing Yu1, Ying Zhong1

  • 1Pharmaron (Ningbo) Technology Development Co., Ltd, No. 800 Bin-Hai 4th Road, Hangzhou Bay New Zone, Ningbo, 315336, China. yunjin.hu@pharmaron.com.

Chemical Communications (Cambridge, England)
|June 18, 2024
PubMed
Summary

A new visible-light photooxidation method creates β-hydroxy sulfones from sulfinate salts and alkenes. This metal-free process efficiently synthesizes Csp3-rich DNA-encoded libraries.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • DNA-encoded libraries (DELs) are powerful tools for drug discovery.
  • Efficient synthesis of diverse chemical scaffolds is crucial for DEL construction.
  • Metal-catalyzed reactions are common but can be limited by substrate scope and purification.

Purpose of the Study:

  • To develop a novel, metal-free method for synthesizing Csp3-rich scaffolds for DNA-encoded libraries.
  • To explore the visible-light photooxidation of sulfinate salts with alkenes.
  • To establish a straightforward and efficient route to β-hydroxy sulfones on DNA.

Main Methods:

  • Visible-light photoredox catalysis was employed.
  • Sulfinate salts were reacted with common alkenes under irradiation.
  • The reaction was performed on DNA-conjugated small molecules.
  • Product characterization involved standard analytical techniques.

Main Results:

  • The reaction successfully yielded β-hydroxy sulfones.
  • Broad substrate compatibility was observed for both sulfinate salts and alkenes.
  • Conversion rates ranged from moderate to excellent.
  • The method proved efficient and straightforward for DNA-encoded library synthesis.

Conclusions:

  • A novel, metal-free visible-light photooxidation enables the synthesis of β-hydroxy sulfones.
  • This method provides an efficient route to Csp3-rich DNA-encoded libraries.
  • The approach offers broad applicability and simplifies library construction for drug discovery.