title: Photocaging of carboxylic acids: a modular approach.
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.
authors.affiliation: Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands).
authors.forename: Wiktor
authors.initials: W
authors.lastname: Szymański
authors.forename: Willem A
authors.initials: WA
authors.lastname: Velema
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry; D008027:Light; D008752:Methylene Chloride / Q000737:chemistry; D017319:Photosensitizing Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D003486:Cyanides; D017319:Photosensitizing Agents; D014867:Water; D008752:Methylene Chloride
keywords: multicomponent reactions; photocaging; protecting groups; synthetic methods; water chemistry