title: Photoinitiated release of an aziridinium ion precursor for the temporally controlled alkylation of nucleophiles.
abstract: A photo-activatable aziridinium precursor has been developed to investigate the possibility of a photo-initiated traditional nucleophilic reaction. The photolysis of a quaternary amine yields a tertiary amine and has allowed us to temporally control aziridinium formation and subsequent alkylation of a colorimetric nucleophilic reporter molecule. We have also used this photo-initiated reaction to alkylate a sulfhydryl group. This new photo-initiated alkylation strategy is water-soluble and expands the toolkit of photo-activated crosslinkers for protein labeling research.
authors.affiliation: Department of Chemistry, University of Massachusetts, Amherst, MA 01003, USA.
authors.forename: Stephen T
authors.initials: ST
authors.lastname: McCarron
authors.forename: Mariel
authors.initials: M
authors.lastname: Feliciano
authors.forename: Jeffreys N
authors.initials: JN
authors.lastname: Johnson
authors.forename: James J
authors.initials: JJ
authors.lastname: Chambers
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D055668:Photochemical Processes
chemical_list: D001388:Aziridines