Lipidated cyclopropenes via a stable 3- N spirocyclopropene scaffold

Tetrahedron Lett. 2018 Sep 12;59(37):3435-3438. doi: 10.1016/j.tetlet.2018.08.010. Epub 2018 Aug 7.


Lipidated cyclopropenes serve as useful bioorthogonal reagents for imaging cell membranes due to the cyclopropene's small size and ability to ligate with pro-fluorescent tetrazines. Previously, the lipidation of cyclopropenes required modification at the C3 position because methods to append lipids at C1/C2 were not available. Herein, we describe C1/C2 lipidation with the biologically active lipid ceramide and a common phospholipid using a cyclopropene scaffold whose reactivity with 1,2,4,5-tetrazines has been caged.

Keywords: Bioorthogonal chemistry; Click chemistry; Cyclopropene tetrazine; Lipid; photocage.