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A programmable chemical switch based on triggerable Michael acceptors.

Jiaming Zhuang1, Bo Zhao1, Xiangxi Meng2

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We developed a novel chemical switch triggered by thiols and amines. This engineerable molecule enables simultaneous bond formation and cleavage, offering tunable and reversible control for diverse applications.

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Area of Science:

  • Chemical Biology
  • Materials Science
  • Organic Chemistry

Background:

  • Developing engineerable chemical reactions with tunable bond formation and cleavage is crucial for biological and materials applications.
  • Orthogonality and external cue-triggering are highly desired features for precise chemical control.

Purpose of the Study:

  • To present a novel chemical switch capable of simultaneous bond formation and cleavage in response to specific external cues.
  • To demonstrate the engineerability and reversibility of this chemical switch for various applications.

Main Methods:

  • Design and synthesis of a Triggerable Michael Acceptor (TMAc) with good leaving groups.
  • Investigation of the "trigger-to-release" and "trigger-to-reverse" mechanisms using thiol and amine triggers.
  • Engineering of five distinct locations within the TMAc for kinetic and reversibility tuning.

Main Results:

  • The thiol/amine-triggerable TMAc enables cascaded release of leaving groups upon initial trigger.
  • A secondary nucleophile trigger can reverse the process, liberating the original thiol/amine.
  • Demonstrated tunable "trigger-to-release" kinetics and tailored reversibility through molecular engineering.

Conclusions:

  • The developed chemical switch offers engineerable, cue-triggerable, and reversible bonding/debonding capabilities.
  • Potential applications include cysteine-selective protein modification, self-immolative linkers, and orthogonally addressable hydrogels.