Sinteza trisaharida β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-D-Fucp

master's thesis

• Title (english): Synthesis of trisaccharide β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-D-Fucp
• Author: Ivana Tuković
• Mentor: Đani Škalamera (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2021-10-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu ovog diplomskog rada biti će pripravljen linearni trisaharid Xyl(β1-4)Rha(α1-2)Fuc,
važna domena imunostimulirajućeg saponina QS-21. Prirodni spoj QS-21, izoliran iz kore
drveta Quillaja saponaria, jedan je od najjačih do sad poznatih adjuvanata, odnosno ključnih
komponenti cjepiva koje poboljšavaju imunološki odgovor na primijenjeni antigen. Linearni
trisaharid biti će sintetiziran iz odgovarajuće zaštićenih monosaharidnih prekursora. Usporedit
će se dvije metodologije glikozilacije: i) upotrebom alila kao zaštitnih/aktivirajućih skupina, te
ii) upotrebom glikozil-fluorida kao donora i sililiranih šećera kao akceptora. Očekivano je da
će druga metoda zbog svoje robustnosti dati bolje rezultate. Prednost te metode je brz i
jednostavan pristup, komercijalno dostupan katalizator, činjenica da nisu potrebni strogi uvjeti
bez vlage i kisika, te da se reakcija provodi pri sobnoj temperaturi. Cilj ovog rada je što
jednostavnijim sintetskim putem i u čim boljem iskorištenju doći do ciljnog linearnog
trisaharida. Međuprodukti u sintezi, kao i konačni produkt biti će okarakterizirani
spektroskopskim metodama (IR, NMR).

Abstract (english)

In this diploma thesis, the linear trisaccharide Xyl(β1-4)Rha(α1-2)Fuc, an important domain of the
immunostimulatory saponin QS-21 was prepared. The natural compound QS-21, isolated from the
bark of Quillaja saponaria tree, is one of the strongest known adjuvants. Adjuvants are the key
components of the vaccine that improve the immune response to the applied antigen. The linear
trisaccharide will be synthesized from protected monosaccharide precursors. Two glycosylation
methods will be compared: i) using allyl as protecting / activating groups, and ii) using glycosyl
fluoride as a donor and silyl ether as an acceptor. The second method is more robust and is expected
to give better results. Advantages of this method are quick and easy approach, the commercially
available catalyst, the fact that strict conditions without moisture and oxygen are not required, and
that the reaction is carried out at room temperature. The aim of this work is to prepare the target
linear trisaccharide in the simplest possible synthetic way and in the best possible yield. The
intermediates in the synthesis, as well as the final product, will be characterized by spectroscopic
methods (IR, NMR).

• Keywords: adjuvanti; cjepiva; glikozilacija; sinteza oligosaharida; Quillaja saponini
• Keywords (english): adjuvants; glycosylation; oligosaccharide synthesis; Quillaja saponins; vaccines
• Language: croatian
• URN:NBN: urn:nbn:hr:217:205920
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2023-10-14
• Created on: 2021-11-05 12:02:21