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A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation.

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  • 1Department of Chemistry , University of California , Berkeley , California 94720 , United States.

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We developed a data-driven method to create new reagents for methionine bioconjugation. This approach enhances adduct stability and enables applications like peptide stapling for improved cellular uptake.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Bioconjugation Chemistry

Background:

  • Developing selective bioconjugation reagents is crucial for chemical biology.
  • Methionine thioether modification offers unique opportunities for bioconjugation.
  • Controlling adduct stability is key for designing effective bioconjugation tools.

Purpose of the Study:

  • To develop a data-driven, physical organic approach for creating methionine-selective bioconjugation reagents.
  • To establish a predictive model for understanding and tuning adduct stabilities.
  • To design and synthesize novel reagents for applications such as peptide stapling.

Main Methods:

  • Utilized statistical modeling of physical organic parameters to predict adduct stability.
  • Employed Redox Activated Chemical Tagging (ReACT) for chemoselective coupling of oxaziridine and methionine thioether.
  • Investigated correlations between sulfimide stability and spectroscopic properties (ν (C═O) stretching frequencies).

Main Results:

  • A predictive model for methionine-adduct stability was developed.
  • A correlation between sulfimide stability and ν (C═O) stretching frequencies was identified.
  • A bis-oxaziridine reagent was synthesized for peptide stapling, demonstrating enhanced cellular uptake of stapled peptides.

Conclusions:

  • A data-driven physical organic strategy can guide the development of bioconjugation reagents with tunable properties.
  • ReACT chemistry and rational design enable the creation of novel tools for thioether modification.
  • This approach has potential applications in chemical biology, drug delivery, and peptide engineering.