Photocaging of Carboxylic Acids: A Modular Approach†
Dr. Wiktor Szymański
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorWillem A. Velema
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ben L. Feringa
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)Search for more papers by this authorDr. Wiktor Szymański
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorWillem A. Velema
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ben L. Feringa
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)Search for more papers by this authorWe thank Claudia Poloni for insightful discussions. Financial support from and the Ministry of Education, Culture and Science (Gravity program no. 024.001.035), Royal Netherlands Academy of Sciences (KNAW academy chair), and European Research Council (ERC Advanced grant 227897) is gratefully acknowledged.
Abstract
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.
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