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

von Wei Wang
Dissertation
Datum der mündl. Prüfung:2020-09-17
Erschienen:2020-10-13
Betreuer:Prof. Dr. Lutz Ackermann
Gutachter:Prof. Dr. Lutz Ackermann
Gutachter:Prof. Dr. Alexander Breder
Gutachter:Prof. Dr. Lutz Tietze
Gutachter:Prof. Dr. Konrad Koszinowski
Gutachter:Dr. Michael John
Gutachter:Prof. Dr. Johannes C. L. Walker
Zum Verlinken/Zitieren: http://dx.doi.org/10.53846/goediss-8217

 

 

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Englisch

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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