Late-Stage Peptide Diversification via Transition Metal-Catalyzed C─H Activation

by Wei Wang
Doctoral thesis
Date of Examination:2020-09-17
Date of issue:2020-10-13
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Alexander Breder
Referee:Prof. Dr. Lutz Tietze
Referee:Prof. Dr. Konrad Koszinowski
Referee:Dr. Michael John
Referee:Prof. Dr. Johannes C. L. Walker
Persistent Address: http://dx.doi.org/10.53846/goediss-8217

 

 

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Abstract

English

The late-stage modification of peptide is of great value to drug discovery and medicinal chemistry. Metal catalyzed C─H activation has emerged as efficient and step-economic strategy for post-translational peptide engineering. Within this thesis, palladium-catalyzed peptide arylation was achieved via isosteric triazole assistance, which was further applied for direct peptide BODIPY fluorescent labeling and the synthesis of BODIPY labeled cyclobutanes. Additionally, low toxicity 3d metal manganese was employed for peptide glycol-conjugation for the first time, delivering glycopeptides and mimetic of naturally occurring glycol-tryptophan. A direct peptide CꟷN formation was developed for highly regioselective peptide C7 amidation, offering an avenue for further peptide diversifications.
Keywords: C–H Activation; Late-Stage Peptide; Chemical Ligation; Fluorescent Labeling; Glyco-conjugation; CꟷN Formation; Tryptophan C7 Activation
 
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