Sinteza i kompleksacijska svojstva glikokonjugata triureidnog anionskog receptora

master's thesis

• Title (english): Synthesis and complexation properties of glycoconjugate tripodal urea anion receptor
• Author: Tin Bobeta
• Mentor: Nikola Cindro (mentor)
• Committee member: Nikola Cindro (predsjednik povjerenstva)
• Committee member: Mirta Rubčić (član povjerenstva)
• Committee member: Nikola Bregović (član povjerenstva)
• Committee member: Josip Požar (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2022-09-20, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Anionski receptori klasa su organskih spojeva koji stvaraju određene nekovalentne
interakcije sa specijama koje nose negativan naboj. Istraživanje tih interakcija (uglavnom
vodikovih veza) u kontekstu odnosa struktura-funkcija od bitnog je značaja kako bi se
priredili što jednostavniji i efikasniji receptori. Cilj ovog rada jest sinteza anionskih receptora
na bazi pentaeritritola te ispitivanje vezanja pojedinih aniona koristeći NMR i UV-Vis
spektroskopiju. Pentaeritritol je tetraol čije molekule sadrže četiri hidroksilne skupine. Polazni
spoj pentaeritritol tribromid podvrgnuti će se prvo azidaciji kako bi se dobio triazid, a potom
supstituciji preostale hidroksilne skupine s metil-jodidom. Zadnja dva sintetska koraka su
redukcija triazida u triamin te reakcija s fenil-izocijanatom u kojoj se formira triureidni
anionski receptor. U sklopu rada, prvo će biti pripravljen navedeni triureidni anionski receptor
koji će poslužiti kao modelni spoj za određivanje afiniteta vezanja odabranih aniona. Nakon
toga, daljnjim će sintetskim modifikacijama biti pripravljen spoj koji se može glikozilirati s
ciljem dobivanja vodotopljivog anionskog receptora.
Svi produkti biti će karakterizirani IR i NMR spektroskopijom.

Abstract (english)

Anion receptors are class of organic compounds that form certain non-covalent interactions
with the species which carry negative charge. Studying these interactions (mostly hydrogen
bonds) in the context of structure-function relationship is essential towards preparing as
simple and efficient receptors as possible. Main goal of this thesis is synthesis of
pentaerythritol based anion receptors and examining binding properties of individual anions
using NMR and UV-VIS spectroscopy. Pentaerythritol is tetraol which molecules contain four
hydroxyl groups. Pentaerythritol tribromide as starting compound will first undergo azidation
to give triazide and then substitution of the remaining hydroxyl group with methyl iodide. The
last two steps in our synthesis path were reduction of triazide into triamine that proceeds to
reaction with phenyl isocyanate which forms tripodal urea receptor. In this thesis, tripodal
anion receptor will be prepared first which will serve as model compound for determining
binding affinity of individual anions. After that, further synthetic modifications will yield
compound that can be glycosylated in order to obtain water soluble anion receptor.
All products will be characterized using NMR and IR spectroscopy.

• Keywords: anioni; klik-kemija; međumolekulske interakcije; ureidni receptori
• Keywords (english): anions; click-chemistry; intermolecular interactions; urea based receptors
• Language: croatian
• URN:NBN: urn:nbn:hr:217:117813
• 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: 2024-09-20
• Created on: 2022-10-07 10:28:50