Modifikacije terminalnih skupina aminokiselina

master's thesis

• Title (english): Modification of amino acids terminal groups
• Author: Željka Žakić
• Mentor: Jasna Vorkapić-Furač (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Biochemical Engineering); (Laboratory for Cell Technology, Application and Biotransformations); Zagreb
• Defense date and country: 2004-10-12, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

U okviru istraživanja na pripravi konformacijski ukočenih premoštenih peptida, istražili su se eksperimentalni uvjeti za pripravu fenilalaninu srodnog aminoketona i N-alkiliranog derivata lizina. U prvom dijelu diplomskog rada opisana je priprava aminoketona 5-[N-(terc-butiloksikarbonil)]amino-6-fenilheks-1-in-4-on (3). Prvi korak u sintezi bio je zaštita amino-skupine fenilalanina. Kao zaštitna skupina korištena je terc-butiloksikarbonilna skupina (Boc). Zatim je reakcijom Grignardovog reagensa 2-propinilmagnezijeva bromida s mješovitim anhidridom aminokiseline pripravljen aminoketon 3. U drugom dijelu diplomskog rada prikazan je slijed za pripravu potpuno zaštićenog N-(2-propinil)-derivata lizina. Komercijalno dostupan derivat lizina Boc-Lys(2-ClZ)-OH (4) prevodi se u etilni ester Boc-Lys(2-ClZ)-OEt (5), a amino-skupina je aktivirana uvođenjem 2-nitrobenzensulfonilne (2-NBS) skupine, pri čemu je dobiven spoj (2-NBS)-Lys(2-ClZ)-OEt (7). U konačnom stupnju provedena je N-alkilacija dodatkom 2-propinil-bromida, te je dobiven spoj (2-NBS)(HC≡CCH)-Lys(2-ClZ)-OEt (8). Svi sintetizirani spojevi karakterizirani su elementarnom analizom i NMR spektroskopijom.

Abstract (english)

As a part of the ongoing studies on the synthesis of bridged peptides with decreased conformational flexibility, experimental conditions for the preparation of the phenylalanine-related aminoketone and N-alkylated derivative of lysine have been studied. In the first part of this work, the preparation of the aminoketone 5-[N-(tert-butyloxycarbonyl)]amino-6-phenylhex-1yn-4-one (3) was described. First step in the synthesis was the protection of the phenylalanine amino group with the tert-butyloxycarbonyl (Boc) protection. Aminoketone 3 was prepared in the reaction of the Grignard reagent 2-propynilmagnesium bromide with the phenylalanine-derived mixed anhydride. The second part of this work describes procedure for the synthesis of the fully protected N-(propin-2-yl) derivative of lysine. The commercially available lysine derivative Boc-Lys(2-ClZ)-OH (4) was converted into the ethyl ester Boc-Lys(2-ClZ)-OEt (5), while the amino group was activated by introducing 2-nitrobenzenesulphonyl (2-NBS) groups (compound 7). In the final step N-alkylation was performed by addition of propin-2-yl bromide giving rise to the compound 8. All compounds prepared were characterized by elemental analysis and 1H NMR and 13C NMR spectroscopy.

• Keywords: aminoketon; N-alkilacija; peptidi
• Keywords (english): aminoketone; N-alkylation; peptides
• Language: croatian
• URN:NBN: urn:nbn:hr:159:849105
• Study programme: Title: Biotechnology; specializations in: Biochemical Engineering; Course: Biochemical Engineering; Study programme type: university; Study level: graduate; Academic / professional title: diplomirani inženjer biotehnologije; smjer biokemijsko inženjerstvo (diplomirani inženjer biotehnologije; smjer biokemijsko inženjerstvo)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-09-12 09:04:08