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Doctoral thesis
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Anion-π Catalysis with Peptides and Synthesis of Thiol-Mediated Uptake Inhibitors

ContributorsPham, Anh Tuan
Number of pages379
Imprimatur date2021-09-27
Defense date2021-09-23
Abstract

In the first topic of this thesis, peptide secondary structure was explored in the design of new anion-π catalysts. The rigid peptide skeleton allows to control the positions of each amino acid residue above the naphthalenediimide surface precisely. When a tertiary amine is placed at different amino acid side chains along the peptide, the catalytic activity of the catalysts could be modulated in a predictable manner. The scope of electron-poor aromatic surface was extended to perylenediimides (PDIs) in the second topic. The helix-like conformation for the peptide backbone has been confirmed with NMR spectroscopy. Overall performance of PDI catalysts was significantly improved in comparison with the NDI analogs. Finally, the application of peptide secondary structures was examined in thiol-mediated uptake. Highly reactive γ-turn peptides were synthesized as potential thiol-mediated uptake inhibitors. With the intention to identify more efficient inhibitors, a large library of thiol-reactive reagents has also been synthesized.

eng
Keywords
  • Anion-π
  • Catalysis
  • Organocatalysis
  • Peptide secondary structure
  • Helical structure
  • Thiol-mediated uptake
  • Inhibitors
Research group
Citation (ISO format)
PHAM, Anh Tuan. Anion-π Catalysis with Peptides and Synthesis of Thiol-Mediated Uptake Inhibitors. 2021. doi: 10.13097/archive-ouverte/unige:155635
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Creation09/26/2021 5:36:00 PM
First validation09/26/2021 5:36:00 PM
Update time03/16/2023 1:35:03 AM
Status update03/16/2023 1:35:02 AM
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