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Systematic Structural Tuning Yields Hydrazonyl Sultones for Faster Bioorthogonal Protein Modification.

Ming Fang1, Gangam Srikanth Kumar1, Qing Lin1

  • 1Department of Chemistry, State University of New York at Buffalo, Buffalo, NY, 14260-3000, USA.

Chembiochem : a European Journal of Chemical Biology
|May 31, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed stable hydrazonyl sultones (HS) with a CF3 group for efficient bioconjugation. These compounds exhibit enhanced aqueous stability and rapid reactivity in click chemistry applications.

Keywords:
Bioorthogonal reactionHydrazonyl sultoneNanobodyNitrile imineTautomerization

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Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Materials Science

Background:

  • Hydrazonyl sultones (HS) are versatile reagents for click chemistry.
  • Improving the aqueous stability and reactivity of HS is crucial for biological applications.
  • Existing HS often suffer from limited stability in aqueous environments, hindering their use.

Purpose of the Study:

  • To synthesize and characterize novel hydrazonyl sultones (HS) with an ortho-CF3 group.
  • To evaluate the aqueous stability and reactivity of these new HS compounds.
  • To demonstrate the utility of HS in bioconjugation reactions with bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN).

Main Methods:

  • Synthesis of hydrazonyl sultones (HS) with varying N-aryl substituents and sultone ring sizes.
  • Characterization of HS stability in aqueous conditions.
  • Investigation of HS reactivity in 1,3-dipolar cycloaddition reactions with BCN.
  • X-ray crystal structure analysis to understand stability mechanisms.
  • Application in the modification of BCN-encoded nanobodies.

Main Results:

  • Novel HS containing an ortho-CF3 group were successfully synthesized in moderate to good yields.
  • X-ray crystallography revealed that CF3 groups electrostatically shield the nitrile imine center, enhancing aqueous stability.
  • Electron-rich, six-membered HS showed excellent aqueous stability and increased cycloaddition reactivity.
  • HS-BCN ligation achieved high second-order rate constants (up to 1500 M⁻¹s⁻¹) in PBS-ethanol, demonstrating fast and selective bioconjugation.

Conclusions:

  • The ortho-CF3 group significantly enhances the aqueous stability of hydrazonyl sultones.
  • N-aryl substituents and sultone ring size modulate HS reactivity and stability.
  • These improved HS reagents enable highly efficient and rapid bioconjugation, advancing applications in chemical biology.