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Tyrosine-Selective Polyfluoroaryl Modification Enables Bioactive Peptides with Enhanced Membrane Permeability and

Quan Zuo1,2, Guoqing Li3, Quanshu He1,2

  • 1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.

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Summary
This summary is machine-generated.

This study introduces a new method for modifying peptides using polyfluoroaryl chemistry. This approach enables efficient peptide ligation and improves cell penetration for drug delivery.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biochemistry

Background:

  • Peptide modification is crucial for developing new therapeutics.
  • Existing methods for peptide functionalization and ligation can be complex and inefficient.

Purpose of the Study:

  • To develop a tyrosine-selective modification strategy for peptides.
  • To enable linker-free peptide ligation and enhance peptide physicochemical properties.

Main Methods:

  • Utilized tetrafluoro-substituted N-methyl luminol reagents for tyrosine modification.
  • Employed mild oxidative conditions for chemoselective functionalization.
  • Confirmed peptide ligation using 19F NMR and X-ray crystallography.

Main Results:

  • Achieved rapid and selective functionalization of tyrosine residues in diverse peptides.
  • Demonstrated successful linker-free peptide-peptide ligation via SNAr reactions.
  • Showcased enhanced membrane permeability and cytosolic delivery of peptides.

Conclusions:

  • Developed a versatile platform for peptide fluorination and ligation.
  • The strategy facilitates programmable peptide assembly and optimization of biological properties.
  • This workflow offers a unified approach for advanced peptide engineering.