prikaz prve stranice dokumenta One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria
Embargo period 2026-07-03
master's thesis
One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria
Zagreb: University of Zagreb, Faculty of Science, 2024. urn:nbn:hr:217:592705
Grdović, Filip
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Grdović, F. (2024). One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:592705

Grdović, Filip. "One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria." Master's thesis, University of Zagreb, Faculty of Science, 2024. https://urn.nsk.hr/urn:nbn:hr:217:592705

Grdović, Filip. "One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria." Master's thesis, University of Zagreb, Faculty of Science, 2024. https://urn.nsk.hr/urn:nbn:hr:217:592705

Grdović, F. (2024). 'One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria', Master's thesis, University of Zagreb, Faculty of Science, accessed 22 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:592705

Grdović F. One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2024 [cited 2024 November 22] Available at: https://urn.nsk.hr/urn:nbn:hr:217:592705

F. Grdović, "One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2024. Available at: https://urn.nsk.hr/urn:nbn:hr:217:592705

Metadata
TitleOne-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria
Title (english)One-pot synthesis of a fully protected trisaccharide from linear oligosaccharide domain of Quillaja saponaria plant saponin
AuthorFilip Grdović
MentorĐani Škalamera (mentor)
Committee memberĐani Škalamera (predsjednik povjerenstva)
Committee memberAdriana Kenđel (član povjerenstva)
Committee memberAleksandra Maršavelski (član povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2024-07-03, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu ovog diplomskog rada sintetiziran je potpuno zaštićeni trisaharid β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-D-Fucp koji je ujedno i strukturna domena saponina QS-21 izoliranog iz biljke Quillaja saponaria, nužna za njegovu imunoadjuvantsku aktivnost. Metoda sinteze glikozidne veze korištena u ovom diplomskom radu koristi glikozil-fluoride kao donore glikozila te sililne etere kao akceptore. Za razliku od standardnih reakcija glikozilacije, ova metoda ne zahtijeva rigorozne suhe uvjete, niti hlađenje na niske temperature, već se odvija uz komercijalno dostupan katalizator, borov trifluorid dietileterat, pri sobnoj temperaturi i u otapalu koje ne mora biti sušeno. Korištenje navedenih prekursora otvara mogućnost tzv. one-pot glikozilacije, odnosno povezivanja nekoliko reakcija glikozilacije u jedan sintetski korak. Strategija one-pot glikozilacije korištena u sintezi ciljnog trisaharida iskorištava suptilne razlike u reaktivnosti različitih sililnih etera. Konačni prekursori i produkt sinteze strukturno su okarakterizirani standardnim spektroskopskim metodama (IR, 1H i 13C NMR).
Abstract (english)
n this diploma thesis, a fully protected trisaccharide β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-D-Fucp was synthesized. This trisaccharide is a structural domain of saponin QS-21, which is isolated from the plant Quillaja saponaria and is essential for its immunoadjuvant activity. The glycosidic bond synthesis method used in this thesis employs glycosyl fluorides as glycosyl donors and silyl ethers as acceptors. Unlike standard glycosylation reactions, this method does not require rigorous dry conditions nor cooling to low temperatures. Instead, it utilizes a commercially available catalyst, boron trifluoride diethyl etherate, at room temperature and in a solvent that does not need to be dried. The use of these precursors opens up the possibility of one-pot glycosylation, connecting several glycosylation reactions into a single synthetic step. The one-pot glycosylation strategy used in this synthesis exploits subtle differences in the reactivity of various silyl ethers. The final precursors and the product were structurally characterized using standard spectroscopic methods (IR, 1H, 13C NMR).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:592705
Study programmeTitle: Graduate university studies in chemistry; specializations in: Graduate university studies in chemistry
Course: Graduate university studies in chemistry
Study programme type: university
Study level: graduate
Academic / professional title: sveučilišni/a magistar/magistra kemije (sveučilišni/a magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsEmbargoed access
Embargo expiration date: 2026-07-03
Terms of useLicence In copyright icon
Created on2024-07-05 09:09:31