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Synthesis of DNA-Encoded Libraries by Tryptophan-Selective Bioconjugation.

Katarzyna Joanna Malawska1, Masashi Suzuki2, Junko Sasaki2

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

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Summary
This summary is machine-generated.

DNA-encoded libraries (DELs) now support diverse chemical reactions. A new tryptophan-selective bioconjugation method enables the creation of complex hydroxypyrroloindoline carboxylic acid (HPIC) scaffolds for drug discovery.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Biotechnology

Background:

  • DNA-encoded libraries (DELs) accelerate ligand discovery by enabling exploration of vast chemical spaces.
  • DEL synthesis is limited by DNA compatibility, restricting the incorporation of complex scaffolds requiring sensitive reactions.
  • Pharmacologically relevant scaffolds often necessitate oxidative or heterocycle-forming reactions, posing challenges for DEL construction.

Purpose of the Study:

  • To develop novel DNA-compatible chemical transformations for expanding DEL structural diversity.
  • To demonstrate the feasibility of incorporating the biologically privileged hydroxypyrroloindoline carboxylic acid (HPIC) scaffold into DELs.
  • To establish a tryptophan-selective bioconjugation method compatible with DEL synthesis.

Main Methods:

  • Utilized a tryptophan-selective bioconjugation strategy employing the keto-ABNOH/TEMPO+ system.
  • Integrated this bioconjugation into the DNA-encoded library synthesis workflow.
  • Validated the compatibility of the reaction with DNA under DEL conditions.

Main Results:

  • The keto-ABNOH/TEMPO+ bioconjugation is fully compatible with DNA-encoded library synthesis.
  • Successfully enabled the construction of the hydroxypyrroloindoline carboxylic acid (HPIC) scaffold within a DEL framework.
  • Expanded the repertoire of accessible chemical structures for DEL-based drug discovery.

Conclusions:

  • The developed tryptophan-selective bioconjugation method overcomes previous limitations in DEL structural diversity.
  • This advancement allows for the incorporation of complex, pharmacologically relevant scaffolds into DELs.
  • Facilitates the discovery of novel ligands and drug candidates through enhanced chemical space exploration.