Hermann Sergej, Wagenknecht Hans-Achim
Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
J Pept Sci. 2017 Jul;23(7-8):563-566. doi: 10.1002/psc.2966. Epub 2017 Jan 31.
The synthesis of peptide-based photocatalysts that use 1-N,N-dimethylaminopyrene as chromophore and their application in photocatalysis is reported. The copper(I)-catalyzed alkyne-azide cycloaddition was applied as key step to prepare the peptide-pyrene conjugates in quantitative yields for different short peptide sequences. The photocatalysts were evaluated for the nucleophilic addition of methanol to 1,1-diphenylethylenes to products with Markovnikov-type orientation The short peptides contain arginine as substrate binding site during photocatalysis, and thus, the reaction was performed without the additive triethylamine that was previously applied as electron shuttle. Full conversion of the substrate and good yields for the addition product were achieved. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.
报道了以1-N，N-二甲基氨基芘为发色团的肽基光催化剂的合成及其在光催化中的应用。铜（I）催化的炔烃-叠氮化物环加成反应作为关键步骤，用于以定量产率制备不同短肽序列的肽-芘共轭物。对光催化剂进行了评估，考察其催化甲醇对1,1-二苯乙烯进行亲核加成反应生成符合马氏规则取向产物的性能。短肽在光催化过程中含有精氨酸作为底物结合位点，因此，该反应在没有先前用作电子穿梭体的添加剂三乙胺的情况下进行。底物实现了完全转化，加成产物的产率良好。版权所有©2017欧洲肽学会和约翰·威利父子有限公司。
