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Org Lett. 2008 Jun 19;10(12):2341-4. doi: 10.1021/ol800284g. Epub 2008 May 27.

Alcohol uncaging with fluorescence reporting: evaluation of o-acetoxyphenyl methyloxazolone precursors.

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  • 1DĂ©partement de Chimie and Laboratoire de Physique Statistique, Ecole Normale SupĂ©rieure, Paris Cedex 05, France.


This paper evaluates a series of photolabile protecting groups with built-in fluorescence reporting. They rely on readily available o-acetoxyphenyl methyloxazolones as activated precursors. Alcohol substrates are easily caged. The resulting photoactivable esters exhibit large one- and two-photon uncaging cross sections. The alcohol substrates are quantitatively released in a 1:1 molar ratio with a strongly fluorescent coumarin coproduct that serves as a reporter to quantify substrate delivery.

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