Priprava i konformacijska analiza ferocenskog dipeptida Boc-L-Pro-Fca-OMe

undergraduate thesis

• Title (english): Preparation and conformational analysis of ferrocene dipeptide Boc-L-Pro-Fca-OMe
• Author: Ana Tarandek
• Mentor: Monika Kovačević (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: 2020-09-01, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

U ovom završnom radu opisani su priprava i konformacijska svojstva ferocenskog dipeptida 1 (Boc-L-Pro-Fca-OMe) koji se pripravlja kopulacijom ferocenske aminokiseline (Fca, I) s L-Pro primjenom standardnog HOBt/EDC postupka. Da bi se ispitao utjecaj uvođenja prolina na tvorbu intramolekulskih vodikovih veza (IHB), te posljedično i na konformacijski prostor koji ferocenski dipeptid zauzima u otopini, provedena je spektroskopska analiza (IR-, NMR- i CD-spektroskopija). Kristalografskom analizom ispitana je mogućnost tvorbe IHB u čvrstom stanju. Pokazalo se da u čvrstom stanju, kao i u otopini dolazi do tvorbe IHB veze koja rezultira 7-članim prstenom, odnosno γ-okretom.

Abstract (english)

The research conducted in this work includes the preparation and structural characterization of ferrocene dipeptide 1 (Boc-L-Pro-Fca-OMe), by copulation ferrocene amino acid (Fca, I) and L-Pro using standard HOBt/EDC method. To examine the effect of proline introduction on formation of intramolecular hydrogen bond (IHB) in solution, the detailed conformational analysis (IR, NMR- and CD-spectroscopy) in solution was performed. Crystallographic structure of dipeptide 2 in solid state was determined to explore possibility of IHB formation. It has been shown that the formation of intramolecular hydrogen bonding in solid state occurs, forming 7-membered ring, i.e. γ-turn. Same pattern is retained in solution state.

• Keywords: peptidi; prolin; ferocen; kristalna struktura; vodikova veza
• Keywords (english): peptides; proline; ferrocene; crystal structure; hydrogen bond
• Language: croatian
• URN:NBN: urn:nbn:hr:159:777338
• 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: 2020-10-29 14:39:27