20.500.12556/DKUM-61958 Epimerizacija ergot alkaloidov in brom-ergot alkaloidov Epimerization of ergot alkaloids and brom-ergot alkaloids Prvi zapisi o ergot alkaloidih in njihovih učinkih segajo že v 7. stoletje pr. n. š., njihovo raziskovanje in odkrivanje pa je doživelo razcvet v 20. stoletju. V medicini se uporabljajo kot sredstva proti migreni, pri zdravljenju Parkinsonove bolezni, kot zdravilo za preprečevanje laktacije, kot agonisti dopamina in drugo. Ergot alkaloidi in brom-ergot alkaloidi obstajajo kot levosučni in desnosučni epimeri. V našem primeru veljajo desnosučni za nezaželene. Desnosučne pretvorimo v levosučne s postopkom epimerizacije, ki poteka prek izolacije soli s kislinami. Cilj diplomskega dela je določiti ustrezno kislino, topilo in procesne pogoje pri postopku epimerizacije ergot alkaloidov in brom-ergot alkaloidov iz desnosučnih v levosučne. Na podlagi analitskih rezultatov, izkoristka in trajanja epimerizacije smo pri ergot alkaloidih kot najustreznejši določili postopek, kjer smo uporabili fosforjevo (V) kislino, za topilo etanol, epimerizacija pa je trajala 24 ur. Pri epimerizaciji brom-ergot alkaloidov pa se je za najprimernejšo izkazala metansulfonska kislina, za topilo etanol in čas epimerizacije 48 ur. The first records of ergot alkaloids and their effects date back to the 7th century BC. Their exploration and discovery peaked in the 20th century. In medicine they are used as antimigraine agents and for treating Parkinson's disease, as a drug for lactation suppression, as dopamine agonists etc. Ergot alkaloids and brom-ergot alkaloids exist in R- or S-form of epimers. In our case, the S-form is undesirable. S-form epimers can be transformed into R-form epimers through epimerization passing through salt isolation with acids. The aim of this study is to determine the appropriate acid, solvent and process conditions in the epimerization process of ergot alkaloids and brom-ergot alkaloids from S-form to R-form. Based on the analytical results, efficiency and duration of ergot alkaloid epimerization, we found that the most appropriate method is to use phosphoric (V) acid, with ethanol as the solvent and epimerization lasting for 24 hours. Methanesulfonic acid proved to be the most appropriate for epimerisation of brom-ergot alkaloids, with ethanol as the solvent and epimerization time of 48 hours. epimerizacija ergot alkaloid brom-ergot alkaloid levosučni desnosučni epimerization ergot alkaloids brom-ergot alkaloids R-form S-form true true false [P. Kladnik] Slovenski jezik Angleški jezik Diplomsko delo/naloga 2016-08-19 14:58:02 2016-09-16 10:18:42 2022-06-28 03:07:06 2019-07-11 12:38:56 2016 0 Maribor 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.945.1(043.2) 20313622 URN:SI:UM:DK:UT6RGS90 VS_Kladnik_Peter_2016.pdf VS_Kladnik_Peter_2016.pdf 1 3BE6A87B2D4274783B01DC3161EAB301 81947bdd1d853f3e15fe38a81a741534a2b06885dd19565d1972e4e773a4eafd 58ea9217-7c0d-11eb-bb7a-00155d0001ca https://dk.um.si/Dokument.php?lang=slv&id=102959 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0