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Merging C(sp3)-H activation with DNA-encoding.

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This study introduces a new DNA-encoded C-H arylation method for drug discovery. This advance expands molecular diversity in DNA-encoded libraries (DELs) by enabling complex scaffold synthesis in water.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery Technologies

Background:

  • DNA-encoded library (DEL) technology accelerates drug discovery by enabling selection of vast molecular libraries.
  • Expanding molecular diversity within DELs requires novel DNA-encoded chemical transformations.
  • C-H activation offers a route to complex molecular scaffolds but faces challenges in DEL formats.

Purpose of the Study:

  • To develop novel DNA-encoded C(sp3)-H activation reactions for increased molecular diversity in DELs.
  • To overcome limitations of aqueous solvents, DNA presence, and low concentrations in DEL chemistry.
  • To enable the synthesis of diverse, complex molecular scaffolds on-DNA.

Main Methods:

  • Palladium-catalyzed C(sp3)-H arylation of aliphatic carboxylic acids, amides, and ketones.
  • Utilizing DNA-encoded aryl iodides as coupling partners in aqueous conditions.
  • Development of on-DNA synthesis strategies for complex molecule generation.

Main Results:

  • Successful C(sp3)-H arylation of various functional groups with DNA-encoded aryl iodides in water.
  • Demonstration of a method compatible with DEL constraints (aqueous solvent, low concentration).
  • On-DNA synthesis of diverse scaffolds with C(sp3) character, chiral centers, and cyclic/heterocyclic motifs.

Conclusions:

  • The developed C-H arylation chemistry significantly expands the molecular diversity accessible through DEL technology.
  • This method provides a versatile platform for generating novel drug-like scaffolds with enhanced complexity.
  • The approach facilitates the use of alternative building blocks, streamlining DEL library construction.