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Chemistry. 2019 Aug 28. doi: 10.1002/chem.201903909. [Epub ahead of print]

A coumarin triflate reagent enables one-step synthesis of photo-caged lipid metabolites for studying cell signaling.

Author information

1
Max-Planck-Institut fur molekulare Zellbiologie und Genetik, Dresden, GERMANY.
2
MPI-CBG, Chemical Biology, Pfotenhauerstr. 108, 01307, Dresden, GERMANY.

Abstract

Photorelease of caged compounds is among the most powerful experimental approaches for studying cellular functions on fast timescales. However, its full potential has yet to be exploited, as the number of caged small molecules available for cell biological studies has been limited by synthetic challenges. Addressing this problem, we developed a straightforward, one-step procedure for efficiently synthesizing caged compounds. We used an in situ generated benzylic coumarin triflate reagent to specifically functionalize carboxylate and phosphate moieties in the presence of free hydroxy groups and generated various caged lipid metabolites, including a number of GPCR ligands. By combining the photo-caged ligands with the respective receptors, we developed an easily implementable experimental platform for the optical control and analysis of GPCR-mediated signal transduction in living cells. Ultimately, the described synthetic strategy allows rapid generation of photo-caged small molecules and thus greatly facilitates the analysis of their biological roles in live cell microscopy assays.

KEYWORDS:

Caged compounds; cell signaling; lipids; one-step synthesis; platelet activating factor

PMID:
31461184
DOI:
10.1002/chem.201903909

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