107500-78-7Relevant articles and documents
Proline-Rich Short Peptides with Photocatalytic Activity for the Nucleophilic Addition of Methanol to Phenylethylenes
Hermann, Sergej,Sack, Daniel,Wagenknecht, Hans-Achim
supporting information, p. 2204 - 2207 (2018/06/04)
Short proline-rich peptides were synthesized and modified with 1-(N,N-dimethylamino)pyrene by copper(I)-catalyzed cycloaddition. They perform photoredox catalysis of the nucleophilic addition of methanol to 1,1-diphenylethylene derivatives into products with Markovnikov orientation. The common additive triethylamine is avoided because forward and backward electron transfer is controlled by substrate binding. A free carboxylic function in the substrate allows more precise substrate binding and defines the electron transfer path better than the unspecific exciplex formation with the substrate bearing a carboxylic ester. A proline-type turn is an advantage for photoredox catalysis, but a proline-induced helix is not required. This is the first successful example for introducing secondarily structured peptides to photoredox catalysis.