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Sinteza novih zaviralcev encima MurA iz glukozamina: primerjava učinkovitosti različnih sinteznih poti = Synthesis of novel MurA enzyme inhibitors from glucosamine: comparison of the efficacy of different synthesis pathways : Uniform Master's Study Programme PharmacyKampl, KlemenNaraščajoča odpornost bakterij proti antibiotikom predstavlja vse bolj akuten izziv za globalni zdravstveni sistem, saj mnoge prej ozdravljive okužbe postajajo manj ozdravljive ali celo ... neobvladljive. Svetovna zdravstvena organizacija (WHO) je uvrstila bakterijsko odpornost proti antibiotikom med tri največje grožnje za javno zdravje v 21. stoletju. Zato je razvoj novih protimikrobnih zdravil postal ena izmed ključnih prioritet, saj je to edini način, da se izognemo eskalaciji te težave. Peptidoglikan je pomemben gradnik bakterijske celične stene, ki se sintetizira v treh različnih delih celice: v citoplazmi, celični membrani in zunaj celice. Prva stopnja reakcijske poti poteka v citoplazmi, kjer encim MurA katalizira pomemben korak. Večina trenutnih protibakterijskih zdravil zavira sintezo peptidoglikana v zadnjih stopnjah sinteze, ki potekajo izven celice. Kljub temu nekaj antibiotikov deluje znotraj celice, med njimi je fosfomicin, ki zavira aktivnost encima MurA v citoplazmi. V tej magistrski nalogi je poudarek na ustvarjanju derivatov glukozamina s pomočjo molekularnega modeliranja in simulacije naravnega substrata. Za ustrezno usmerjanje funkcionalnih skupin in izdelavo reverzibilnih zaviralcev smo za osnovo izbrali skelet glukozamina, ki lahko prodre skozi celično steno in membrano bakterij ter doseže encim MurA v njihovem notranjem okolju. Glavni cilj je bil razviti sintezno pot za pripravo potencialnih zaviralcev encima MurA, ki so modificirani s fragmenti na mestu C-6, ter atomu N-1. Osredotočili smo se na uporabo nove zaščitne skupine BDA, ki smo jo uvedli na mesti C-3 in C-4. Pred uvedbo BDA smo zaščitili amin z zaščitno skupino Cbz. Nato smo poskušali optimizirati pogoje, ter razmerje reagentov za uvedbo BDA. Ko nam sinteze v naslednjem koraku več niso uspevale, smo se odločili za opustitev BDA in se vrnili na sintezo preko uveljavljenih zaščitnih skupin (tritilna na C-6, benzilni na C-3 in C-4). Na koncu smo na mesto C-6 pripeli kloroetil acetat oz. bromometil acetet. Pri tej sintezni poti smo se osredotočili na prednosti in slabosti, ter težave, ki so se nam pojavljale.Type of material - master's thesis ; adult, seriousPublication and manufacture - Ljubljana : [K. Kampl], 2024Language - slovenianCOBISS.SI-ID - 201036547
Author
Kampl, Klemen
Other authors
Frlan, Rok
Topics
Bakterijska rezistenca |
odpornost proti antibiotikom |
peptidoglikan |
glukozamin |
zaviralci |
encim MurA |
BDA |
butan-2,3-dion
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Library/institution |
City | Acronym | For loan | Other holdings |
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Faculty of Pharmacy, Ljubljana | Ljubljana | FFALJ |
reading room 1 cop.
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Database name | Field | Year |
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Kampl, Klemen | ![]() |
Frlan, Rok | 26512 |
Source: Personal bibliographies
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