Late-Stage Peptide Functionalization by Ruthenium-Catalyzed C H Arylations and Alkylations
by Alexandra Schischko
Date of Examination:2018-10-24
Date of issue:2018-11-08
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Dietmar Stalke
Referee:Prof. Dr. Manuel Alcarazo
Referee:Dr. Franziska Thomas
Referee:Dr. Shoubhik Das
Referee:Dr. Alexander Breder
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Abstract
English
The thesis contents methods for the selective activation and functionalization of C–H bonds of the C2 position of a tryptophan moiety incorporated into peptides. Palladium-catalyzed C-H arylation reactions applying diaryliodonium tosylates are shown, as well as ruthenium-catalyzed C-H arylation reactions applying aryl bromides and iodides, and ruthenium-catalyzed C-H alkylation reactions using vinyl ketones and acrylates. The developed procedures could be successfully applied to peptides for labeling with fluorophores, and ligation including twofold C-H activation.
Keywords: C-H activation; ruthenium; palladium; peptide; tryptophan