Visible-Light Absorbing, Photolabile, Quinone-Based Protecting Groups for Alcohols and Amines

Abstract

A new strategy for producing caged alcohols and amines that can be released (decaged) with visible light has been developed. A series of quinone-based structures has been produced, and the mechanism of decaging has been investigated by a number of techniques, including kinetic isotope effects, stereochemical probes, and nanosecond laser flash photolysis. The reaction proceeds cleanly with moderate to good efficiencies in water. Irradiation of a caged-GABA prodrug with a 455 nm LED resulted in activation of GABA_A receptors (α1β2ϒ2 subtype) expressed in Xenopus oocytes. Further mechanistic studies as well as efforts to move to longer wavelengths will be described.

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