20.500.12556/RUL-161340 Sinteza nenaravne aminokisline s tritilno zaščitno skupino za sintezo peptidov na trdnem nosilcu Synthesis of an unnatural amino acid with trityl protecting group for solid-phase peptide synthesis Namen diplomskega dela je bila sinteza nenaravnega analoga histidina s tritilno zaščito, ki smo jo izvedli z baker(I) katalizirano azid-alkin cikloadicijo. Sinteza je temeljila na uporabi tritil azida v reakciji z Fmoc-L-propargilglicinom, za neposredno uvedbo tritilne skupine v strukturo triazola. Najprej smo s podobno reakcijo, z uporabo tritil azida in 1-etinil-4-fluorobenzena poskušali pripraviti 1,4-disubstituiran-1,2,3-triazol, kar nam je tudi uspelo. Opazovali smo stabilnost pripravljenega 4-(4-fluorofenil)-1-(trifenilmetil)-1H-1,2,3-triazola pod rahlo kislimi pogoji in v prisotnosti baze. Na osnovi reakcije za pripravo opisanega, sterično oviranega triazola, smo s podobnim postopkom uspeli sintetizirati nenaravno aminokislino, tj. nenaravni analog histidina, in reakcijo optimizirali s ciljem po čim višji konverziji. Na koncu smo poskušali aminokislino uporabiti v metodi sinteze peptidov na trdnem nosilcu (SPPS) za pripravo krajšega peptida. The aim of this thesis was the synthesis of an unnatural histidine amino acid analogue by copper(I) catalysed azide-alkyne cycloaddition. The synthesis was based on the use of trityl azide with Fmoc-L-propargylglycine, enabling the incorporation of trityl protecting group into triazole structure. Firstly, we attempted to prepare 1,4-disubstituted-1,2,3-triazole by a similar reaction, using trityl azide and 1-ethynyl-4-fluorobenzene, which successfully resulted in 4-(4-fluorophenyl)-1-(trimethyl)-1H-1,2,3-triazole. We were monitoring the change in the structure of this molecule depending on the presence of acidic or basic conditions in the solvent. Based on the described reaction for the preparation of sterically hindered triazole, we were able to synthesise described unnatural amino acid by a slightly improved procedure and optimised the reaction to maximise the conversion. Finally, we attempted using synthesized amino acid in solid-phase peptide synthesis (SPPS) for the preparation of simple peptide. tritil azid azid-alkin cikloadicija klik kemija aminokislina triazoli trityl azide azide-alkyne cycloaddition click chemistry amino acid triazoles true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2024-09-10 09:00:01 2024-09-10 09:00:09 2024-11-08 13:43:28 0000-00-00 00:00:00 2024 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 25295 214287619 Bogovic_Domen_-_Sinteza_nenaravne_aminokisline_s_tritilno_zascitno_skupino_za_sintezo_peptidov_n.pdf Bogovic_Domen_-_Sinteza_nenaravne_aminokisline_s_tritilno_zascitno_skupino_za_sintezo_peptidov_n.pdf 1 927FB14550172ED1FE02BE5459032EE5 28f0e0ed64a6fb0bbb629ab933dc61047bab782274253f4110ece390cf3a5da9 504642cf-6f42-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=190244 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0