Optimizacija sinteze dipikolinatnih ligandov za vezavo na kovinske ione

Čačulovič, Monika (avtor), Perdih, Franc (mentor)

Dandanes se veliko študij usmerja v preučevanje kovinskih kompleksov z derivati dipikolinske kisline, saj je bila interakcija kovinskih ionov z ligandi prepoznana kot pomembno področje za raziskave zdravljenja sladkorne bolezni. Glavni cilj diplomskega dela je bila optimizacija reakcije sinteze prekurzorjev organskih ligandov, pri kateri sem želela dobiti produkt s čim višjim izkoristkom ter čistostjo. V okviru eksperimentalnega dela sem v laboratoriju iz dipikolinske kisline sintetizirala spojino dimetil piridin-2,6 dikarboksilat, ki sem jo uporabila kot izhodno spojino za sintezo 6-metoksikarbonilpiridin-2-karboksilne kisline, ki je bil končni produkt sinteze. Izvedla sem 17 reakcij za optimizacijo sinteznega postopka. Osnovno recepturo sem pridobila iz literature in jo postopoma spreminjala. Pri sintezah sem spreminjala maso izhodne spojine, prostornino topila, vrsto in koncentracijo baze ter množinsko razmerje med reaktantoma. Reakcije sem izvedla pri različnih temperaturah in časih mešanja. Vsak dobljen produkt sem okarakterizirala z 1H NMR spektroskopijo in preverila njegovo čistost. Uspela sem optimizirati sintezni postopek, pri katerem sem dobila ponovljive rezultate z izkoristki, ki so se gibali med 79 in 99 %. Sintetiziran produkt je bil visoke čistosti in je uporaben za nadaljnje sinteze ligandov, ki so primerni za vezavo na kovinske ione.

• Jezik: Slovenski jezik
• Ključne besede: dipikolinska kislina, sladkorna bolezen, optimizacija, 1H NMR, kovinski ioni
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2022
• PID: 20.500.12556/RUL-139372
• COBISS.SI-ID: 124478211
• Datum objave v RUL: 01.09.2022

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Optimization of dipicolinate ligand synthesis for binding to metal ions

Izvleček

Nowadays many studies are focused on the research of metal complexes with dipicolinic acid derivatives. The interaction of metal ions with ligands is recognized as an important area of research on diabetes treatments. The main goal of this thesis was the optimization of precursors of organic ligands synthesis in which I wanted to obtain a product with the highest possible yield and purity. As part of the experimental work the compound dimethyl pyridine-2,6-dicarboxylate was synthesized from dipicolinic acid. The synthesized acid was then used as a starting compound for the synthesis of 6-methoxycarbonylpyridine-2-carboxylic acid, which was the desired product of the synthesis. Seventeen reactions were performed to optimize the synthesis procedure. The initial recipe was obtained from literature where gradual changes were introduced. During the optimization process I changed the mass of the starting compound, the volume of the solvent, the type and concentration of the base and the mass ratio between the reactants when compared to the starting recipe. The reactions were performed at different temperatures and mixing times. I characterized each obtained product by 1H NMR spectroscopy and checked its purity. I managed to optimize the synthesis procedure in which I obtained reproducible results with yields ranging between 79 and 99%. The synthesized product was of high purity and is useful for further syntheses of ligands suitable for binding to metal ions.

• Ključne besede: dipicolinic acid, diabetes, optimization, 1H NMR, metal ions