الفهرس 
ABSTRACTOnly 14 pages are availabe for public view
 |  | from | 166 |  |  |
| | | from | 166 | | |
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.