Photoremovable protecting groups are a useful concept for organic synthesis and biological applications. They are currently on demand especially for poor leaving groups (LG), such as amines. Two main approaches are currently available: (i) protection of amines as the 2-nitrobenzyl derivatives, photorelease of which is accompanied by complex secondary chemistry and formation of toxic side-products, (ii) protection of amines via a carbamate linker, which is synthetically more difficult and the subsequent photoinitiated release is slow.We introduce a new application of the 4-hydroxyphenacyl (pHP) chromophore as a protecting group for the amine function of amino acids and amines. The protected compounds are easily synthesized from pHP bromide and the amine, and the aqueous solution photolysis of their ammonium salts frees the amine in nearly quantitative yields along with the non-toxic and poorly-absorbing photo-Favorskii reaction side-product, 4-hydroxyphenylacetic acid (scheme). This promising strategy overcomes the previous difficulties and thereby represents a clean and efficient deprotection method.                                                                                                     Acknowledgement : AMVIS/KONTAKT ME 09021

<i>p</i>-Hydroxyphenacyl as a photoremovable protecting group for amines and amino acids

240th National Meeting (2010)

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p-Hydroxyphenacyl as a photoremovable protecting group for amines and amino acids