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Dithioesters: simple, tunable, cysteine-selective H2S donors.

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Dithioesters can be tuned to release hydrogen sulfide (H2S) upon reaction with cysteine. Modifications to dithioester structure control the release rate, aiding H2S chemical biology studies.

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Area of Science:

  • Polymer Chemistry
  • Chemical Biology
  • Organic Synthesis

Background:

  • Dithioesters are versatile compounds with established roles in RAFT polymerization.
  • The chemical reactivity of dithioesters, particularly their potential for controlled functional group release, remains an area for exploration.

Purpose of the Study:

  • To investigate the potential of dithioesters as tunable motifs for controlled hydrogen sulfide (H2S) release.
  • To explore the influence of structural and electronic modifications on the rate of cysteine-mediated H2S release.
  • To elucidate the kinetic and mechanistic pathways governing the reaction between dithioesters and cysteine.

Main Methods:

  • Synthesis of various dithioester derivatives.
  • Kinetic studies monitoring H2S release upon reaction with cysteine.
  • Density Functional Theory (DFT) calculations to support mechanistic interpretations.

Main Results:

  • Demonstrated that dithioesters release H2S upon reaction with cysteine.
  • Showcased that structural and electronic modifications allow for tunable rates of H2S release.
  • Identified the initial attack by cysteine as the rate-limiting step in the reaction, supported by DFT calculations.

Conclusions:

  • Dithioesters represent a tunable platform for controlled H2S release.
  • Understanding the reaction mechanism facilitates the rational design of dithioester-based probes for chemical biology.
  • These findings pave the way for advanced applications of dithioesters in studying H2S biology.