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January 1, 2019Organic & Biomolecular Chemistry

The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation

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Authors

LCLonghuai ChengNankai UniversityXKXueying KangNankai UniversityDWDan WangCentral South University

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Implication

Experimental study demonstrates one-pot dual bioorthogonal functionalization via tandem Staudinger and SPAAC reactions in living cells, suggesting versatile tools for biomolecular labeling.

Key Points

  • Develop a catalyst-free, one-pot dual-functionalization platform by coupling the nonhydrolysis Staudinger reaction with Staudinger-Bertozzi or SPAAC ligations without protective groups.
  • Engineered a bisazido linker possessing both a tetrafluorinated aromatic azide and an alkyl azide for selective sequential labeling.
  • Evaluated relative reaction rates and kinetics using HPLC analysis and fluorescence assays across reaction partners.
  • Synthesized molecular conjugates in one-pot configurations and performed dual-color bioimaging of a FRET-based dyad in living cells.
  • The nonhydrolysis Staudinger reaction proceeded significantly faster on the tetrafluorinated aromatic azide than Staudinger-Bertozzi or SPAAC ligations on the alkyl azide.
  • Tandem one-pot assembly delivered molecular beacon 7 via Staudinger-Bertozzi ligation in 32% recovery yield and compound 8 via SPAAC ligation in 59% recovery yield.
  • Tandem nonhydrolysis Staudinger and SPAAC reactions successfully generated an active FRET dyad directly inside living cells.

Cite This Study

Cheng et al. (2019) studied this question.

synapsesocial.com/papers/6aa0fcaeb6ff41cbc45b88eahttps://doi.org/10.1039/c9ob00528e
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