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Abstract The thesis is presented in 4 chapters: Chapter 1: The chemical similarity of antibacterial cyclic peptides and peptidomimetics was studied in order to identify new promising cyclic scaffolds. A large descriptor space coupled with cluster analysis was employed to digitize known antibacterial structures and to gauge the potential of new peptidomimetic macrocycles, which were conveniently synthesized by acylbenzotriazole methodology. Some of the synthesized compounds were tested against an array of microorganisms and showed antibacterial activity against Bordetella bronchistepica, Micrococcus luteus, and Salmonella typhimurium. Chapter 2: Optimized selective S-acylations of cysteine esters gave intermediates for the synthesis of macrocyclic peptoids via benzotriazole methodology. Chapter 3: Nα-Boc-Nim-4-toluenesulfonyl-L-histidinoylbenzotriazole enables convenient acylation of N-, O- , S- and C- nucleophiles with no detectable racemization. We report efficient syntheses of novel histidine-containing di-, tri-, and tetra-peptides and models for the preparation of potentially biologically active histidine N-, O- , S- and C- conjugates. Chapter 4: Amino acid and peptide conjugates of quinine were synthesized in 52-95% yields using benzotriazole methodology under microwave irradiation. |