TPDYs: strained macrocyclic diynes for bioconjugation processes
A terphenyl diyne (TPDY) macrocycle, 3,5-TPDY, has been developed incorporating a bent 1,3-diyne that is active in SPAAC processes affording atropoisomeric triazole products, as well as cycloadditions with diazoacetates and tetrazines. A pendant amine allowed bioconjugation of TPDY to two proteins in a microbial transglutaminase-catalyzed reaction. In contrast to many cycloalkyne SPAAC reagents, the TPDY stabilization occurs <i>via</i> interactions of π and π* orbitals of the adjacent alkynes.
Authors
- Radu Iftimie
- Rebecca L. Davis (ORCID: https://orcid.org/0000-0002-0679-6025)
- Joelle N. Pelletier (ORCID: https://orcid.org/0000-0002-2934-6940)
- Corentin Cruché
- Shawn K. Collins (ORCID: https://orcid.org/0000-0001-9206-5538)
- Adem Hadjabdelhafid-Parisien (ORCID: https://orcid.org/0000-0001-6519-4561)
- Kirsten N. Hurdal
- Bernard D'Onofrio
Institutions
- Centre in Green Chemistry and Catalysis (CA)
- University of Manitoba (CA)
Publication Details
- Journal
- Chemical Communications
- Published
- 2024-12-04
- DOI
- https://doi.org/10.1039/d4cc05367b
- Citations
- 1
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.25