Hydrophilic photolabile protecting groups (PPGs) for hydroxyl protection have been developed by Pengfei Wang and co-workers from the University of Alabama at Birmingham.
PPGs are protecting groups that can be removed with photo irradiation, they very useful tools in a range of basic and applied research areas. One of these applications is their use as ‘photocages’ where the photochemical removal of the photogages often takes place in aqueous environments meaning that solubility issues are central to the use of caged biomolecules.
This team have previously developed a novel PPG for hydroxyl groups, 3-(dimethylamino)trityl (DMATr) but its hydrophobicity obstructs its wide applications in aqueous environments so in their recently published PPS article they report their efforts to improve its water solubility. The new PPGs the team developed were derived from DMATr by replacing the two methyl groups with two hydrophilic butyryl groups. The new PPG reagents can be readily prepared and installed. They are stable in the dark but can be removed cleanly and efficiently in aqueous environments upon irradiation with a UV lamp or sunlight.
This paper is part of a themed issue on photoremovable protecting groups due to be published in 2012.
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Development of hydrophilic photolabile hydroxyl protecting groups
Haishen Yang, Lei Zhou and Pengfei Wang
Photochem. Photobiol. Sci., 2012, DOI: 10.1039/C1PP05281K
