Priprava merkaptopurinskih biokonjugata ferocena

undergraduate thesis

• Title (english): Preparation of ferrocene mercaptopurine bioconjugates
• Author: Klara Komarec
• Mentor: Jasmina Lapić (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2023-09-14, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Organometalni derivati nukleobaza (OrDeN-i) nova su generacija konjugata u kojima su povezani metaloceni s temeljnim strukturnim elementima nasljeđivanja. Reakcijom između ferocenoil klorida i purinskih nukleobaza pripravljeno je niz konjugata s karbonilnom poveznicom između heterocikličkog i organometalnog djela u kojem je omjer produkta (N7/N9-ferocenoil izomera) reguliran prostornim svojstvima supstituenta na C6 položaju. U okviru ovog završnog rada pripravljeni su merkaptopurinski biokonjugati ferocena. Aciliranje se provodi s ferocenoil kloridom, u acetonitrilu uz trietilamin kao deprotonirajući agens pri čemu u reakciji s merkaptopurinom nastaje uz monoderivat N7 i bisderivat N9/C6, dok je reakcija s 6-metilmerkaptopurinom regiospecifična reakcija pri čemu nastaje samo N9 produkt. Strukture svih sintetiziranih spojeva karakterizirane su spektrometrijskim tehnikama: NMR i IR spektroskopijom za točnu identifikaciju svakog izomera.

Abstract (english)

Organometallic derivatives of nucleobases (OrDeNs) are a new generation of conjugates in which metallocenes are connected to the basic structural elements of inheritance. The reaction between ferrocenoyl chloride and purine nucleobases prepared a series of conjugates with a carbonyl link between a heterocyclic and an organometallic part, in which the product ratio (N7/N9 -ferrocenoyl isomer) is regulated by the spatial properties of the substituent at the C6 position. As part of this final work, mercaptopurine bioconjugates of ferrocene were prepared. Acylation is carried out with ferrocenoyl chloride, in acetonitrile with triethylamine as a deprotonating agent, whereby in the reaction with mercaptopurine, the monoderivative N7 isomer and the bis derivative N9/C6 are formed, while the reaction with 6-methylmercaptopurine is a regiospecific reaction in which only the N9 product is formed. The structures of all synthesized compounds were characterized by spectrometric techniques: NMR and IR spectroscopy for accurate identification of each isomer.

• Keywords: 6-merkaptopurin; ferocenoil klorid; regioselektivnost; NMR spektroskopija
• Keywords (english): 6-mercaptopurine; ferrocenoyl chloride; regioselectivity; NMR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:159:712967
• Study programme: Title: Biotechnology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-04-29 08:56:28