| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1375427 | Bioorganic & Medicinal Chemistry Letters | 2008 | 5 Pages |
Abstract
The new BODIPY systems 1 and 2 were prepared and then used as substrates to explore SNAr and F-B displacement reactions. Chloride was easily displaced from 1 by a piperidine/ester, methylmagnesium bromide selectively displaced fluoride, and cyanide could attack both sites. System 2 readily added soft nucleophiles to the electrophilic carbon atoms, providing a new method for bioconjugation of BODIPYs to proteins while also introducing a 19F probe.
Graphical abstractStudies of SNAr and B-F displacement reactions on 1 lead to the development of probe 2 that can be directly added to nucleophilic amino side-chains of proteins.Figure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Lingling Li, Binh Nguyen, Kevin Burgess,