Sinteza novih heterocikličih beta-D-galaktokonjugata kao potencijalnih inhibitora butirilkolinesteraza. Homogena kataliza i nastava kemije.

master's thesis

• Title (english): Synthesis of novel beta-D-galactoconjugates as potential butyrylcholinesterase inhibitors. Homogeneous catalysis and teaching chemistry.
• Author: Lorena Kordić
• Mentor: Srđanka Tomić-Pisarović (mentor)
• Mentor: Nenad Judaš (mentor)
• Committee member: Srđanka Tomić-Pisarović (predsjednik povjerenstva)
• Committee member: Nenad Judaš (član povjerenstva)
• Committee member: Perica Mustafić (član povjerenstva)
• Committee member: Božena Mitić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Biology); Zagreb
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2017-02-28, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Biology

Abstract

U okviru istraživačkog dijela ovog diplomskog rada pripravljeni su novi heterociklički β-D-galaktokonjugati kao potencijalni inhibitori butirilkolinesteraza. U prvom koraku slobodne hidroksilne skupine D-galaktopiranoze zaštićene su acetiliranjem. Potom je na anomerni C-atom peracetilirane D-galaktopiranoze direktnom metodom O-glikozidacije uz BF3·Et2O kao aktivator vezan 2-brometanol do nastanka 1,2-trans galaktozida (β-anomer). Heterociklički spojevi (piridin, imidazol, benzimidazol te njihovi metilni i benzilni derivati) povezani su sa prethodno pripravljenim peracetiliranim β-D-galaktozidom i zatim su u posljednjem koraku uklonjene zaštitne skupine metodom po Zemplénu, natrijevim metoksidom u metanolu. Struktura i čistoća svih pripravljenih spojeva okarakterizirana je standardnim spektroskopskim analitičkim postupcima (IR, MS, NMR) te mjerenjem optičkog skretanja.
U metodičkom dijelu rada osmišljen je prijedlog nastavnog sata na temu „Homogena kataliza“. Glavni i najčešći problem nastave na ovu temu je da se katalitička uloga tvari često pripisuje tvrdnjom, a ne prepoznaje se na temelju mjerenih podataka. Prijedlog nastavnog sata temelji se na strategiji učenja otkrivanjem i sadrži niz pokusa, kojima se omogućuje da učenici uz pomoć nastavnika, obave mjerenja, otkriju zakonitosti i prepoznaju katalitičku ulogu pojedinih tvari.

Abstract (english)

The scope of the thesis research part was the preparation of seven novel heterocyclic
β-D-galactoconjugates as potential butyrylcholinesterase inhibitors. In the fisrt step, all hydroxyl groups of D-galactopyranose were protected by acetylation. Then 2-bromoethanole was attached to the anomeric C-atom of peracetylated D-galactopyranose, using the direct method of O-glycosylation, in the presence of BF3·Et2O as an activator, to form 1,2-trans galactoside (β-anomer). The heterocyclic compounds (pyridine, imidazole, benzimidazole and their 1-methyl and 1-benzyl derivatives) were attached to the previously synthesised acetylated β-D-galactoside and then, in the last step, the products were deacetylated following the Zemplén method, by adding sodium methoxide in methanol. The structures and purity of all obtained compounds were characterised by standard analytical procedures (IR, MS, NMR) and by optical rotation measurements.
In the methodical part of the thesis, a proposition of a teaching lesson, on the subject matter of homogeneous catalysis, was designed. The main and the most common problem with teaching this subject matter is the practice of determing the catalytic properties of a compound by statements and not by the measurment data. The proposition of the teaching lesson is based on the strategy of inquiry learning with special emphasis on the use of experiments which allow students to collect the measurement data, discover the science laws and recognise the catalytic role of certain compounds.

• Keywords: β-D-galaktokonjugati; heterociklički spojevi; inhibitori butirilkolinesteraza; učenje otkrivanjem; homogena kataliza
• Keywords (english): β-D-galactoconjugates; heterocycles; butyrylcholinesterase inhibitors; homogeneous catalysis; inquiry-based learning
• Language: croatian
• URN:NBN: urn:nbn:hr:217:939161
• Study programme: Title: Integrated undergraduate and graduate university study of Biology and Chemistry Education; specializations in: Integrated undergraduate and graduate university study of Biology and Chemistry Education; Course: Integrated undergraduate and graduate university study of Biology and Chemistry Education; Study programme type: university; Study level: integrated undergraduate and graduate; Academic / professional title: magistar/magistra edukacije biologije i kemije (magistar/magistra edukacije biologije i kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2017-04-20 09:39:17