Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Kenji Watanabe, Nodoka Terao, Takashi Niwa, Takamitsu Hosoya
Abstract
To enhance the practicality of photouncaging system using 3-acyl-2-methoxyindolizines, direct acylation of indolizines with carboxylic acids was developed using condensation reagents, generally used for peptide coupling. This method allowed for caging a broad range of carboxylic acids with indolizines. The method enabled a facile synthesis of water-soluble caged bioactive carboxylic acids having an intramolecular photosensitizer. The efficient release of carboxylic acids from the synthesized caged compounds upon red light irradiation was confirmed in neutral buffered solutions.
Topics & Concepts
ChemistryAcylationCarboxylic acidReagentIntramolecular forcePhotosensitizerOrganic chemistryCombinatorial chemistryCatalysisSynthesis and Reactivity of HeterocyclesChemical Synthesis and AnalysisPhotochromic and Fluorescence Chemistry