engleski

Novel Aminonaphthalene Photocages for Carboxylic Acids and Alcohols Applied in Organic Synthesis and Biology

Photoremovable protecting groups, also known as photocages, are unique subclass of protect- ing groups which can be removed in photochemical reactions. Photodeprotection reactions often occur under mild conditions without harmful reagents, which is the main reason for their use, not only in synthetic organic chemistry, but also in other fields like medicine and biology [1, 2]. Hydroxymethylaniline derivatives were recently demonstrated as potential photocages for alcohols and carboxylic acids [3]. The efficiency of photodecaging was investigated and it was found out that the meta-derivatives are better photocages for alcohols, whereas the ortho- derivatives are better protective groups for carboxylic acids. Encouraged by these results, dif- ferent substituted aminonaphthalenes as potential photocag- es for alcohols and carboxylic acids were prepared and their photochemistry was investigated in detail by preparative irradiations, fluorescence spectroscopy, and laser flash pho- tolysis. The scope of deprotection has been demonstrated on biologically important carboxylic acids (ibuprofen, keto- profen, etc.) and alcohols (glucose, n-hexanol, etc.).

Aminonaphthalene Photocages ; Protecting Groups ; Photochemical Reactions

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