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13.
Sinteza 3-ketopalmitoil koencima A : [Prešernove nagrade študentom]
Košak, Urban
17ß-hidroksisteroid-dehidrogenaza tipa 12 je encim, ki sodi v družino 17ß-hidroksisteroid-dehidrogenaz in katalizira redukcijo estrona v estradiol. Poleg vloge pri steroidogenezi naj bi imel vlogo ...tudi pri presnavljanju lipidov. Kataliziral naj bi redukcijo 3-ketoacil koencima A v 3-hidroksiacil koencim A. Ta redukcija je druga stopnja mikrosomalnega podaljševanja maščobnih kislin. S sintezo potencialnega endogenega substrata, 3-ketopalmitoil koencima A, bi prispevali k raziskovanju potencialne multifunkcionalnosti tega encima in s tem k razvoju novih učinkovin za nekatera rakava obolenja, motnje presnove in različne genetske ter nevrodegenerativne bolezni, s katerimi so povezane 17ß-hidroksisteroid-dehidrogenaze. Ker smo za sintezo 3-ketopalmitoil koencima A potrebovali etil 3-oksoheksadekanoat, smo razvili enostaven postopek za sintezo Ž,Ž-nesubstituiranih in Ž-monosubstituiranih Ž-keto estrov iz kislinskih kloridov in etil acetoacetata. S tem postopkom smo sintetiziralietil 3-oksooktanoat, etil 3-okso-3-fenilpropanoat, etil 3-(4-nitrofenil)-3-oksopropanoat, etil 3-(4-klorofenil)-3-oksopropanoat in etil 3-oksoheksadekanoat, ki smo ga uporabili za sintezo 3-ketopalmitoil koencima A. Sinteza končne spojine 3-ketopalmitoil koencima A je bila mogoča le z uvedbo zaščitne skupine za Ž-karbonilno skupino. Za določanje čistosti 3-(1',3'-dioksolanil)palmitoil koencima A in 3-ketopalitoil koencima A ter spremljanje poteka pretvorbe 3-(1',3'-dioksolanil)palmitoil koencima A v 3-ketopalitoil koencima A smo razvili več HPLC metod.
Type of material - research project
Publication and manufacture - Ljubljana : [Košak U.], 2012
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