[1] New photoprotecting groups: Desyl and p-hydroxyphenacyl phosphate and carboxylate esters

Add time:07/12/2019    Source:sciencedirect.com

This chapter introduces two new phototriggers for caging nucleotides, amino acids, peptides, and related functional group derivatives, potentially including higher-order homologs. These new phototriggers have several advantages that favor them over the conventional o-nitrobenzyl derivatives, including a more rapid release of the substrate by a primary photochemical fragmentation process; adequate to excellent aqueous solubility; and stable, benign photoproducts. Added attractive features for the p-hydroxyphenacyl phototrigger include its rearrangement to a phenylacetic acid, thus shifting the chromophore absorption to a shorter wavelength, eliminating its interference with the incident radiation. Finally, the absence of a chiral center eliminates diastereomeric mixtures during synthesis.It is anticipated that these features will result in added demand for use of α-keto phototriggers for many new applications in biochemistry and physiological studies.

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