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master's thesis
Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom
Zagreb: University of Zagreb, Faculty of Science, 2021. urn:nbn:hr:217:578503
Logožar, Ivan
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Logožar, I. (2021). Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:578503

Logožar, Ivan. "Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:578503

Logožar, Ivan. "Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:578503

Logožar, I. (2021). 'Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom', Master's thesis, University of Zagreb, Faculty of Science, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:578503

Logožar I. Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:217:578503

I. Logožar, "Izolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:217:578503

Metadata
TitleIzolacija i derivatizacija saponina iz ekstrakta kore drveta Quillaja saponaria u svrhu priprave konjugata s desmuramil-dipeptidom
Title (english)Isolation and derivatization of saponin from the extract of Quillaja saponaria tree bark for the synthesis of conjugates with desmuramyl dipeptide
AuthorIvan Logožar
MentorĐani Škalamera (mentor)
Committee memberĐani Škalamera (predsjednik povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberJana Pisk (član povjerenstva)
Committee memberVesna Petrović Peroković (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2021-11-17, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Za sintezu konjugata Quillaja saponina i desmuramil-dipeptida u ovom diplomskom radu pripravljena su tri ključna prekursora. Konjugacija triterpenskog saponina i desmuramil dipeptida planirana je preko D-galakturonske kiseline, koja je izosterička s D-fukozom, prisutnom u prirodnom QS-21. Derivat D-galakturonse kiseline potreban za sintezu konjugata bit će pripravljen u nekoliko koraka polazeći iz komercijalno dostupne D-galakturonske kiseline monohidrata. Triterpenski saponin biti će izoliran iz komercijalno dostupnog ekstrakta kore QS, nakon čega će biti zaštićen odgovarajućim zaštitnim skupinama. Desmuramil dipeptid sintetizirat će se polazeći iz odgovarajućih amonikiselina. Rad će uključivati izolaciju, derivatizaciju i karakterizaciju prirodnih spojeva sintetske metode peptidne ugljikohidratne kemije. Cilj rada je pronalazak efikasnog sintetskog puta do ključnih prekursora potrebnih za pripravu konjugata Quillaja saponina i desmuramil-dipeptida. Ove dvije jedinice zasebno posjeduju izraženu imunoadjuvantsku aktivnost pa je pretpostavka da će njihovo povezivanje dovesti do sinergističkog efekta u povećanju aktivnosti. Također, uloga šećernog dijela nije zanemariva, jer je poznato da oblik u kojem se nalazi šećer kod derivata Quillaja saponina (slobodne OH skupine ili u obliku acetilnih estera) može značajno promijeniti smjer imunološkog odgovora (Th1/Th2).
Abstract (english)
Three key intermediates needed for the synthesis of Quillaja saponin and desmuramyldipeptide conjugate were prepared in this diploma thesis. Conjugation of the triterpene precursor and desmuramyldipeptide was planned through D-galacturonic acid, which is isosteric with D-fucose, which occurs naturally in QS-21. D-Galacturonic acid derivative needed for this synthesis will be prepared in a few steps, starting from commercially available D-galacturonic acid monohydrate. The triterpene precursor will be isolated from commercially available Quillaja saponaria tree bark extract, after which it will be protected by appropriate protective groups. Desmuramyldipeptide will be prepared from its corresponding aminoacids. This thesis will include isolation, derivatization and characterization of natural compounds, as well as, synthetic methods of peptide and carbohydrate chemistry. The goal of this thesis was to find the most efficient synthetic pathway to these precursors needed to prepare Quillaja saponin and desmuramyldipeptide conjugate. These two precursors have extraordinary immunoadjuvant activity by themselves, and the ultimate goal is to show the synergistic effect by combining the two. The sugar component is also crucial in this conjugate, as it can drastically change the direction of the immune response (Th1/Th2).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:578503
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: 2023-11-17
Terms of useLicence In copyright icon
Created on2021-12-06 12:58:48