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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Sulfonium-Tethered Peptide.

Yuena Wang1, Feng Yin1, Zigang Li2

  • 1Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, People's Republic of China.

Methods in Molecular Biology (Clifton, N.J.)
|June 27, 2022
PubMed
Summary
This summary is machine-generated.

We developed novel methods for creating stapled peptides, enhancing their stability and cell penetration for therapeutic applications. These sulfonium-tethered peptides offer improved drug delivery potential.

Keywords:
Reversible modificationStapled peptideSulfonium

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Area of Science:

  • Medicinal Chemistry
  • Biotechnology
  • Drug Delivery

Background:

  • Stapled peptides are promising therapeutics due to enhanced membrane penetration and in vivo stability.
  • Existing methods for peptide modification can be complex and time-consuming.

Purpose of the Study:

  • To develop efficient methods for creating stable and permeable stapled peptides.
  • To focus on Met-Met and Cys-Met bis-alkylation strategies for peptide macrocyclization.
  • To generate sulfonium-tethered peptides for improved drug delivery and biological applications.

Main Methods:

  • Utilized chemical ligation and cyclization (CIH) and TD coupling.
  • Employed methionine-methionine (Met-Met) bis-alkylation strategy.
  • Applied cysteine-methionine (Cys-Met) bis-alkylation strategy for peptide macrocyclization.

Main Results:

  • Developed efficient synthesis routes for stapled peptides.
  • Generated sulfonium-tethered peptides with enhanced stability and cell permeability.
  • Demonstrated the potential of these peptides for drug delivery applications.

Conclusions:

  • Met-Met and Cys-Met bis-alkylation strategies provide efficient routes to stable, permeable stapled peptides.
  • Sulfonium-tethered peptides are valuable for drug delivery and broader biological applications.
  • The developed methods simplify the synthesis of advanced peptide therapeutics.