2. Academic Validation
  3. Development of Biocompatible Ene-Ligation Enabled by Prenyl-Based β-Caryophyllene with Triazoline/Selectfluor under Physiological Conditions

Development of Biocompatible Ene-Ligation Enabled by Prenyl-Based β-Caryophyllene with Triazoline/Selectfluor under Physiological Conditions

  • J Org Chem. 2022 Jul 1;87(13):8648-8655. doi: 10.1021/acs.joc.2c00841.
Sheng Wang 1,  Yuanyuan Li 1,  Hongling Zhou 1,  Li Wang 2,  Rui Wang 1 3
Affiliations

Affiliations

  • 1 The Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, China.
  • 2 Wuhan No. 1 Hospital, Huazhong University of Science and Technology, Wuhan, Hubei 430022, China.
  • 3 Shenzhen Huazhong University of Science and Technology Research Institute, Shenzhen, Guangdong 518057, China.
PMID: 35708493 DOI: 10.1021/acs.joc.2c00841
Abstract

Here, we first report a rapid and highly selective biocompatible ligation that proceeds via a strain-promoted prenyl-involved [2, 3]-Ene rearrangement process. We demonstrate the usefulness of naturally occurring strain-promoted β-caryophyllene with triazoline (PTAD)/Selectfluor in the study of tagging molecule-of-interest. Experiments in peptide (Histone H3 (1-21) and Myhc (614-629)) and protein (BSA, βLG, and HSP40) models exemplified the utility of the Ene-ligation for in vivo imaging and tracking.

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