HomePh.D. Study at IOCBArchive - 2011Organic chemistry

Organic chemistry

Tutor RNDr. Václav Čeřovský, CSc.
Team Václav Čeřovský
Topic Synthesis of cyclic antimicrobial peptides using intramolecular cyclization reactions

Antimicrobial peptides represent new hope in the fight against resistant pathogenic bacteria. Several novel peptides possessing potent antimicrobial activities were recently discovered in our laboratory. Most of them are linear amphipathic α-helical peptides. The side chain-to-side chain cyclization can be employed to stabilize this specific conformation and to reduce susceptibility toward proteolytic degradation. The study will focus on the synthesis of cyclic antimicrobial peptides by: (1) intramolecular “click reaction” based on Cu(I)-catalyzed reaction between side chains of ω-azido and ω-alkynyl amino acids incorporated into peptide chain forming 1,4-disubstitued[1,2,3]triazolyl-containing bridge. (2) using the method of hydrocarbone stapling utilizing „ring-closing olefin metathesis“ catalyzed with Grubbs catalyst. The study will also involve biophysical methods for structural studies and biological assays.