20.500.12556/RUL-161075 Sinteza histidinskega analoga za sintezo peptidov na trdnem nosilcu Synthesis of a histidine analogue for solid support peptide synthesis Cikloadicija med alkini in azidi ob prisotnosti bakrovega katalizatorja je reakcija, pri kateri nastanejo 1,4-disubstituirani 1,2,3-triazoli. Reakcija spada v t.i. »klik« kemijo, ki predstavlja vedno bolj pomembno področje sodobne kemije. V sklopu diplomskega dela smo se ukvarjali z opisano reakcijo, in sicer, smo spajali 1-bromo-2-etinil benzen in tritil azid in pri tem sintetizirali nov 1,4-disubstituiran 1,2,3-triazol. Pripravili smo tudi terminalni alkin s tritilno skupino, ki smo ga poizkušali spajati s tritil azidom. Prav tako smo predstavili način priprave nenaravne aminokisline. Tritil azid smo reagirali z N-Fmoc-L-propargilglicinom ob prisotnosti ustreznega liganda, baze in bakrovega katalizatorja. Sintezo smo nadaljnje preučili in opazovali vpliv reakcijskih pogojev ter reagentov na izkoristek sinteze. Tako pripravljen zaščiteni analog histidina s triazolnim obročem smo nato uporabili za sintezo peptida z metodo sinteze peptidov na trdnem nosilcu (SPPS). The cycloaddition between alkynes and azides in the presence of a copper catalyst is the reaction that leads to the corresponding 1,4-disubstituated 1,2,3-triazoles. It belongs to the so-called "click" chemistry, which represents more and more important field of modern chemistry. We have combined 1-bromo-2-ethynyl benzene and a trityl azide to synthesise a new 1,4-disubstituted 1,2,3-triazole. Terminal alkyne with a trityl group was also prepared and was attempted to couple with a trityl azide. Following developed protocol, we have developed a reaction for the preparation of the modified amino acid. The trityl azide was reacted with N-Fmoc-L-propargylglycine in the presence of the appropriate ligand, base and copper catalyst. We investigated the reaction with respect to reaction conditions, including equivalents of reagents, to achieve high conversion. The prepared protected histidine analogue with a triazole ring was then used for the synthesis of the peptide using solid-phase peptide synthesis (SPPS) approach. cikloadicija triazol nenaravna aminokislina histidinski analog peptid SPPS cycloaddition triazole non-canonical amino acids histidine analogue peptide SPPS true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2024-09-06 14:20:00 2024-09-06 14:20:08 2024-10-30 10:48:22 0000-00-00 00:00:00 2024 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 25297 213406979 Brinovec_Spela_-_Sinteza_histidinskega_analoga_za_sintezo_peptidov_na_trdnem_nosilcu.pdf Brinovec_Spela_-_Sinteza_histidinskega_analoga_za_sintezo_peptidov_na_trdnem_nosilcu.pdf 1 A57CC56C175279A8774A19BEF21422D2 1d8ab6e9f96c566a20be290be150c22617112c4855735b26e1ebfb8bfe9b5157 5a179d97-6c4a-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=189939 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0