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master's thesis
Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida
Zagreb: University of Zagreb, Faculty of Science, 2019. urn:nbn:hr:217:112814
Ožegović, Antonija
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Ožegović, A. (2019). Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:112814

Ožegović, Antonija. "Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida." Master's thesis, University of Zagreb, Faculty of Science, 2019. https://urn.nsk.hr/urn:nbn:hr:217:112814

Ožegović, Antonija. "Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida." Master's thesis, University of Zagreb, Faculty of Science, 2019. https://urn.nsk.hr/urn:nbn:hr:217:112814

Ožegović, A. (2019). 'Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida', Master's thesis, University of Zagreb, Faculty of Science, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:112814

Ožegović A. Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2019 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:217:112814

A. Ožegović, "Razvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2019. Available at: https://urn.nsk.hr/urn:nbn:hr:217:112814

Metadata
TitleRazvoj sintetskih metoda za pripravu triazolnih derivata manoziliranog desmuramil-dipeptida
Title (english)Development of synthetic methods for the preparation of triazole derivatives of mannosylated desmuramyl dipeptide
AuthorAntonija Ožegović
MentorVesna Petrović Peroković (mentor)
MentorĐani Škalamera (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberŽeljka Soldin (član povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberĐani Škalamera (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2019-09-20, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu diplomskog rada ispitana je mogućnost strukturnog modificiranja desmuramil-dipeptida uvođenjem manozne i triazolne podjedinice supstituirane adamantanom. Kao polazni dipeptid pripravljen je Boc-L-alanil-D-glutaminska kiselina 6 (Boc-L-Ala-D-Glu(OBn)-OH). Adamantilom supstituirana triazolna podjedinica uvedena je na dipeptid azid-alkin cikloadicijom (klik-reakcija). Terminalna alkinska komponenta za klik-reakciju pripravljena je propargiliranjem α-karboksilne skupine glutaminske kiseline dipeptida 6 s propargilaminom pri čemu je dobiven propargilirani dipeptid 8, dok je 1-azidoadamantan (11) pripravljen iz adamantan-1-ola. Klik-reakcijom spojeva 8 i 11 dobiven je adamantilom modificiran dipeptid 12. Benzilima zaštićena manozna podjednica 4 sintetizirana je u nekoliko koraka iz polaznog metil-α-D-manopiranozida i vezana preko glikolne poveznice na terminalnu amino-skupinu alanina spoja 8, s kojeg je prethodno uklonjena Boc zaštita, dajući zaštićeni manozilirani propargilirani dipeptid 10. Klik-reakcijom spojeva 10 i 11 pripravljena je zaštićena ciljna molekula 13. Konačni cilj diplomskog rada jest optimizirati ključne korake u sintezi (priprava dipeptida, propargiliranje, klik-reakcija, vezanje manozne podjedinice) u smislu priprave izomerno čistih spojeva što će se primijeniti za pripravu različitih triazolnih derivata manoziliranog desmuramil-dipeptida u svrhu priprave novih adjuvanata.
Abstract (english)
Structural modification of desmuramyl dipeptide by incorporation of mannose and adamantyl triazole subunit was investigated in this diploma thesis. Dipeptide Boc-L-alanyl-D-glutamic acid 6 (Boc-L-Ala-D-Glu(OBn)-OH) was prepared first. Adamantyl triazole subunit was incorporated to peptide structure by azide-alkyne cycloaddition (the click-reaction). Terminal alkyne part for the click reaction was prepared by propargylation of α-carboxyl group of glutamic acid on dipeptide 6 using propargyl amine. Thus, propargylated dipeptide 8 was obtained. Azide component, 1-azidoadamantane (11), was prepared from adamantan-1-ol. Click-reaction of compounds 8 and 11 resulted in adamantyl dipeptide conjugate 12. Benzylated mannose unit 4 was prepared in few steps from methyl-α-D-mannopyranoside. It was connected to terminal amino group of alanine in 8 through glycolic acid which gave benzylated mannosylated propargyl dipeptide 10. Boc protection was removed from compound 8 prior to that step. Click-reaction of 10 and 11 gave target compound 13. The aim of this thesis was to optimize the key synthetic steps (preparation of dipeptide, propargylation, click-reaction, incorporation of mannose unit) in order to obtain pure isomers. This optimized steps will be applied in the preparation of various triazole derivatives of mannosylated desmuramyl dipeptide as potential new adjuvants.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:112814
Study programmeTitle: Graduate university studies in chemistry; specializations in: Research programme
Course: Research programme
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2021-09-20
Terms of useLicence In copyright icon
Created on2019-10-02 14:33:12