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Water-Based Dynamic Depsipeptide Chemistry: Building Block Recycling and Oligomer Distribution Control Using

Martin C1,2, Moran Frenkel-Pinter1,2, Kelvin H Smith2,3

  • 1School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

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Summary
This summary is machine-generated.

This study introduces depsipeptides, copolymers of amino and hydroxy acids, for reversible chemistry. These novel building blocks enable dynamic polymer formation and breakdown under mild conditions, overcoming limitations of traditional peptide chemistry.

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Amide bond formation's high kinetic barrier limits reversible chemistry applications, including peptide-based dynamic libraries.
  • Existing dynamic peptide chemistry strategies often require harsh conditions, catalysts, or specific functional groups.
  • Depsipeptides, copolymers of amino and hydroxy acids, offer a biorelevant alternative to overcome these limitations.

Purpose of the Study:

  • To explore depsipeptides as a novel system for dynamic and reversible polymer chemistry.
  • To develop a model system using N-(α-hydroxyacyl)-amino acid building blocks for reversible depsipeptide formation.
  • To investigate the controllable polymerization and depolymerization of depsipeptides.

Main Methods:

  • Developed a model system of N-(α-hydroxyacyl)-amino acid building blocks.
  • Utilized two-step evaporation-rehydration cycling under moderate conditions for polymerization.
  • Exploited differential hydrolytic lifetimes of amide and ester bonds, controlled by pH, temperature, time, and side chains, for selective recycling.

Main Results:

  • Demonstrated reversible polymerization of depsipeptides via dynamic ester chemistry facilitated by cyclic morpholinedione intermediates.
  • Showed that polymerization and breakdown are controllable by adjusting solution conditions and building block side chains.
  • Established that structural properties dictate depsipeptide half-lives and product oligomer distributions.

Conclusions:

  • A cyclic, ester-based reversible depsipeptide formation mechanism was established, temporally separating polymerization and depolymerization.
  • This system overcomes limitations of traditional amide-based dynamic chemistries.
  • Findings have potential implications for prebiotic polymer chemical evolution and the development of new dynamic materials.