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Photocaging of Carboxylic Acids: A Modular Approach
Author(s) -
Szymański Wiktor,
Velema Willem A.,
Feringa Ben L.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402665
Subject(s) - isocyanide , chemistry , dichloromethane , aldehyde , modular design , combinatorial chemistry , ugi reaction , carboxylic acid , component (thermodynamics) , organic chemistry , computer science , catalysis , physics , solvent , thermodynamics , operating system
Photocaged compounds are important tools for studying and regulating multiple processes, including biological functions. Reported herein is the use of the Passerini multicomponent reaction for modular preparation of photocaged carboxylic acids. The reaction is compatible with several functionalities and proceeds smoothly both in water and dichloromethane. The choice of aldehyde determines the wavelength used for deprotection and enables formation of orthogonally protected products. The isocyanide component can be used for introduction of reactive tags and photosensitizers, as well as for immobilization on a solid support.