Biokonjugati ferocena i derivata purina: sinteza i spektralna karakterizacija

master's thesis

• Title (english): Bioconjugates of ferrocene and purine derivatives: synthesis and spectral characterization
• Author: Marija Tratnik
• Mentor: Senka Djaković (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: 2019-03-28, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Konjugati ferocena i nukleobaza novija su skupina bioorganometalnih spojeva čiju strukturu čine biološki i elektrokemijski aktivne komponente. Ferocen pokazuje dobru membransku permeabilnost, nisku toksičnost i antitumorsko djelovanje čime je omogućena primjena takvih kopulata u biologiji, farmaciji i drugim znanostima. Sinteza ferocenskih derivata nukleobaza temelji se na sintetskoj kopulaciji pri čemu razmak između ferocena i heterocikličkog dijela čine alkilni ili karbonilni lanci. Ovaj diplomski rad prikazuje sintezu i spektroskopsku karakterizaciju novih ferocenoil purinskih biokonjugata te praćenje regioselektivnosti reakcija aciliranja NMR spektroskopijom. Aciliranje se provodi s ferocenoil-kloridom/mješovitim ferocenskim anhidridom, a kao produkt većine reakcija nastaje smjesa N9- i N7-izomera čiji sadržaj ovisi o nukleobazi i njenim supstituentima. Omjeri nastalih izomera u reakcijskoj smjesi određeni su praćenjem reakcijske smjese NMR spektroskopijom i kvantitativnom integracijom pikova koji odgovaraju pojedinom izomeru.

Abstract (english)

Ferocene-nucleobase conjugates are a newer group of bioorganometallic compounds whose structure is made up of biologically and electrochemically active components. Ferrocene exhibits good membrane permeability, low toxicity and antitumor activity, enabling the use of such conjugates in biology, pharmacy and other sciences. The synthesis of ferrocene nucleobase derivatives is based on synthetic copulation where the spacer between ferrocene and heterocyclic moiety of the molecule are alkyl or carbonyl chains. This graduate thesis presents the synthesis and spectroscopic characterization of new ferrocenoyl purine conjugates and monitoring the regioselectivity of acylation reactions by NMR spectroscopy. The acylation is carried out with ferrocenoyl chloride/mixed ferrocene anhydride, and in most of reactions the product is a mixture of N9 and N7 isomers whose content depends on the nucleobase and its substituents. The ratios of isomers in reaction mixture are determined by monitoring of the reaction mixture by NMR spectroscopy and quantitative integration of peaks corresponding to each isomer.

• Keywords: purin; supstituirani derivati purina; ferocen; spektralna analiza
• Keywords (english): purine; substituted purine derivatives; ferrocene; spectral analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:502246
• Study programme: Title: Molecular Biotechnology; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka molekularne biotehnologije (magistar/magistra inženjer/inženjerka molekularne biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2019-12-06 13:16:16