Within this thesis, we were developing methods for incorporation of unnatural fragments, specifically compounds of the dicarba-closo-dodecaborane class (carboranes), into polypeptide chains and synthesizing peptides. The selection of carboranes was based on their potential use in medicine, where they can mimic carbocyclic frameworks and are of interest for BNCT (Boron Neutron Capture Therapy) due to their high boron content. The incorporation of carboranes into peptides was carried out in various ways. The most important among them was based on the preparation of N-hydroxysuccinimide (NHS) esters and their reaction with the ε-amino group of the lysine side chain. We prepared two different NHS reagents containing the carborane group and tested bioconjugation reactions on model peptides, which we prepared in advance. The incorporation of carboranes into peptides was also achieved via activated dicarba-closo-dodecaborane carboxylic acid with subsequent coupling, and by the preparation of a carborane-functionalized amino acid, which was introduced into the peptide using automated SPPS. In paralel, we worked on development of method for peptide synthesis through preparation of shorter polypeptides using green solvents, unprotected amino acids, and more cost-effective activators.
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