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

Lipidated cyclopropenes via a stable 3-N spirocyclopropene scaffold.

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Department of Chemistry, Stony Brook University, Stony Brook, NY, 11790, United States.


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.


Bioorthogonal chemistry; Click chemistry; Cyclopropene tetrazine; Lipid; photocage

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