20.500.12556/RUL-139157 Sinteza derivatov L-arginina iz N-benziloksikarbonil-L-ornitina Synthesis of derivatives of L-arginine from N-benzyloxycarbonyl-L-ornithine V sklopu diplomskega dela smo želeli pripraviti del tetrapeptidne elektrofilne sonde, in sicer Arg(Boc)2-SerOMe (4). Uspešno smo sintetizirali N-Cbz-Arg(Boc)2-OH (1) iz N-Cbz-Orn(Boc)-OH in N,N'-Boc2-S-metilizotiosečnine. Spojino 1 smo nato spojili s serin metil estrom hidrokloridom v dipeptid N-Cbz-Arg(Boc)2-SerOMe (2) v prisotnosti treh različnih aktivacijskih reagentov: CDI, EEDQ in EDC. Pri tem se je kot stranski produkt tvoril α-N-benziloksikarbonil-ω,ω'-di-N-t-butoksikarbonil-L-arginin laktam (3). Poskus zmanjšanja deleža spojine 3 je bil neuspešen. V zadnjem koraku sinteze spojine 4 smo spojini 2 selektivno odstranili Cbz zaščitno skupino s katalitskim hidrogeniranjem. As a part of my Bachelor's thesis we aimed to prepare a part of a tetrapeptide electrophilic probe, namely Arg(Boc)2-SerOMe (4). N-Cbz-Arg(Boc)2-OH (1) was successfully synthesized from N-Cbz-Orn(Boc)-OH and N,N'-Boc2-Smethylisothiourea. Compound 1 was then coupled with serine methyl ester hydrochloride to the dipeptide N-Cbz-Arg(Boc)2-SerOMe (2) in the presence of three different coupling reagents: CDI, EEDQ and EDC. α-N-benzyloxycarbonyl-ω,ω'-di-N-tbutoxycarbonyl-L-arginine lactam (3) was formed as a by-product. An attempt to reduce the proportion of compoud 3 was unsuccessful. As a last step in the synthesis of compound 4, Cbz protecting group was selectively removed from compound 2 by catalytic hydrogenation. dipeptid aktivacijski reagenti zaščitna skupina hidrogenoliza dipeptide coupling reagents protecting group hydrogenolysis true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2022-08-31 14:35:00 2022-08-31 14:35:03 2022-09-22 13:16:31 0000-00-00 00:00:00 2022 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 22007 122508291 Suhorepec_Nadja_-_Sinteza_derivatov_L-arginina_iz_N-benziloksikarbonil-L-ornitina.pdf Suhorepec_Nadja_-_Sinteza_derivatov_L-arginina_iz_N-benziloksikarbonil-L-ornitina.pdf 1 B9CD03A3B135C14A1C8E52A40D229089 0721b822aa8e92d770667d51176b37ff3046de7a311fcc143f5bd384733e3a50 4d971c6f-2929-11ed-92af-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=159696 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0