20.500.12556/DKUM-99744 Sinteza in karakterizacija maleimidno terminiranega 1,2-bis(2-kloroetoksi)etana Synthesis and characterization of maleimide-terminated 1,2-bis(2-chloroethoxy)ethane V diplomskem delu smo obravnavali sintezo in karakterizacijo povezovalne molekule oziroma linkerja, katerega namen je povezovanje fluorofore z biološko molekulo. Cilj dela je bila priprava molekule s terminalno maleimidno skupino, ki bi omogočala nadaljnjo vezavo na izbrano biološko molekulo. Delo je temeljilo na pretvorbi funkcionalnih skupin na terminalnih delih izhodne spojine bis-[2-(2-kloroetoksi)etil]etra. Najprej smo z nukleofilno substitucijo uspešno sintetizirali azidni intermediat, ki smo ga nato poskušali reducirati do primarnega amina. Redukcijo smo izvedli na dva načina, in sicer s Staudinger-jevo redukcijo s trifenilfosfinom ter z litijevim aluminijevim hidridom. Pri Staudinger-jevi redukciji je težavo predstavljalo predvsem ločevanje produkta od trifenilfosfin oksida, pri redukciji z LiAlH4 pa smo dobili trden produkt. Poleg redukcije smo preizkusili tudi različne pogoje za okso nukleofilno substitucijo preostale terminalne kloridne skupine. Pri tem smo uporabili različne kisikove nukleofile in baze ter spremljali njihov vpliv na potek reakcije. Nastale produkte smo analizirali z NMR spektroskopijo. Pri nekaterih reakcijah nastanka željenega produkta ne moremo potrditi. Sinteze končnega produkta nismo uspeli dokončati. Dobljeni rezultati so lahko osnova za nadaljnjo optimizacijo sinteze. In this diploma thesis, we investigated the synthesis and characterization of a linking molecule, or linker, intended to connect a fluorophore with a biological molecule. The aim of the work was to prepare a linker with a terminal maleimide group that would enable subsequent conjugation to a selected biological molecule. The work was based on the modification of functional groups at the terminal ends of the starting compound bis-[2-(2-chloroetoxy)ethyl]ether. First, an azide intermediate was successfully synthesized by nucleophilic substitution and was then subjected to reduction to obtain the corresponding primary amine. The reduction was carried out using two different methods: the Staudinger reduction with triphenylphosphine and reduction with lithium aluminium hydride. In the Staudinger reduction, the main challenge was the separation of the product from triphenylphosphine oxide, while the reduction with LiAlH4 resulted in a solid product. In addition, different reaction conditions for the oxo-nucleophilic substitution of the remaining terminal chloride group were investigated. Different oxygen nucleophiles and bases were used, and their effects on the course of the reaction were evaluated. The obtained products were mainly analyzed by NMR spectroscopy. In some reactions, the formation of the desired product could not be confirmed. The synthesis of the final product could therefore not be completed. The obtained results may serve as a basis for further optimization of the synthesis. organski azidi nukleofilna substitucija Staudinger-jeva redukcija litijev aluminijev hidrid maleimidi NMR spektroskopija organic azides nucleophilic substitution Staudinger reduction lithium aluminum hydride maleimides NMR spectroscopy true true false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2026-08-25 16:45:04 2026-09-28 08:05:33 2026-09-28 08:05:36 0000-00-00 00:00:00 2026 0 Maribor 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 UN_Vuckovic_Ana_2026.pdf UN_Vuckovic_Ana_2026.pdf 1 07DD2D98C5F750DA5BFDE7BC792CCB08 38d50e77399c21a481a3a2f7547b40f377ba2199080002dd0e79803705456aa2 b8f2e191-ad2e-11f1-b668-00155d0001be https://dk.um.si/Dokument.php?lang=slv&id=212118 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0