Author, Institution: Monika Iškauskienė, Kaunas University of Technology
Science area, field of science: Natural Sciences, Chemistry, N003
Scientific Supervisor: Prof. Hab. Dr. Algirdas Šačkus (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
Dissertation Defence Board of Chemistry Science Field:
Prof. Dr. Vytautas Getautis (Kaunas University of Technology, Natural Sciences, Chemistry, N003) – chairperson
Dr. Sonata Krikštolaitytė (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
Prof. Dr. Vladimir Kryštof (The Czech Academy of Science, Institute of Experimental Botany and Palacky University, Czech Republic, Natural Sciences, Biochemistry, N004)
Prof. Dr. Linas Labanauskas (Center for Physical and Technological Sciences, Natural sciences, Chemistry, N003)
Prof. Dr. Vytas Martynaitis (Kaunas University of Technology, Natural Sciences, Chemistry, N003)
The dissertation defence was held remotely.
The doctoral dissertation is available at the library of Kaunas University of Technology (K. Donelaičio g. 20, Kaunas).
Annotation:
Over the past several decades, bioactive peptides have been attracting scientific interest due to their ability to interact with receptors or inhibit protein–protein interactions. However, most peptides are denoted by low lipophilicity, high molecular weights and charged functional groups; as a result, they are unable to cross the intestinal epithelial barrier. For these reasons, in order to improve the properties of the native peptides, such as their biological activity and metabolic stability, unnatural amino acids (UAAs) are usually used as rigidifying elements.
An effective method for convenient synthesis of new amino acid-like building blocks from easily accessible starting materials has been developed. 5-[1-(tert-Butoxycarbonyl)azetidin-3-yl]-1H-pyrazole-3-carboxylate was easily N-alkylated with various types of alkyl halogenides with the objective to obtain two separable regioisomers suitable for the building-block library. Easily accessible N-Boc-3-iodoazetidine was used as the N-alkylating agent in the reaction with commercially available pyrazole and indazole carboxylates so that to extend the variety of synthetic amino acids. Pyrazole and the piperidine ring were easily connected by the N-alkylation reaction with mesylate activated nucleophile. Pyrazolo[4,3-c]pyridine was easily N-alkylated with various types of alkyl halogenides to obtain two separable regioisomers suitable for the building-block library. The carbonyl group of two selected indole-3-acetic acids was transformed into a 1,3,4-oxadiazole ring. The prepared 1,3,4-oxadiazoles possess antioxidant properties at low concentrations.
March 23 d. 11:00
Dissertation Defense Hall at Kaunas University of Technology (K. Donelaičio g. 73-403, Kaunas)
Įtraukti į iCal
