One-pot sinteza potpuno zaštićenog trisaharida iz linearne oligosaharidne domene saponina biljke Quillaja saponaria

master's thesis

• Title (english): One-pot synthesis of a fully protected trisaccharide from linear oligosaccharide domain of Quillaja saponaria plant saponin
• Author: Filip Grdović
• Mentor: Đani Škalamera (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Adriana Kenđel (član povjerenstva)
• Committee member: Aleksandra Maršavelski (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2024-07-03, 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: adjuvanti; glikozil-fluoridi; one-pot glikozilacija; sililni eteri; Quillaja saponini
• Keywords (english): adjuvants; glycosyl fluorides; one-pot glycosylation; silyl ethers; Quillaja saponins
• Language: croatian
• URN:NBN: urn:nbn:hr:217:592705
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2026-07-03
• Created on: 2024-07-05 09:09:31