Konjugati ferocena s aminokiselinama i beta-laktamom

master's thesis

• Title (english): Conjugates of ferrocene with amino acids and beta-lactam
• Author: Nina Bjeliš
• Mentor: Veronika Kovač (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: 2007-07-06, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

Prema postupcima opisanim u literaturi pripravljeni su Boc-Ala-β-Alm (2, 81%), Ala-β-Alm (3, 47%), ferocenkarboksilna kiselina (5, 53%), tert-butil-1'-karboksi-1-ferocenkarbamat (13, 93%) i ferocen-1,1'-di(karbonil-klorid) (15, 86%). Spojevi 5 i 13 dali su u reakcijama s Ala-β-Alm 3 u prisutnosti EDC i HOBt (N-ferocenoil-Ala)-β-Alm (6, 40%) odn. Boc-Fca-Ala-β-Alm (14, 49%). Kopulacijom 15 s Ala-β-Alm (3) dobiva se Fn(CO-Ala-β-Alm)2 (16, 25%). Struktura β-laktamskog konjugata 2 i ferocenskih peptidnih derivata 6, 14 i 16 potvrđena je spektroskopskim metodama (IR, 1H-NMR i 13C-NMR). IR- i 1H-NMR-analizom izučavana je mogućnost stvaranja i jakost intramolekulskih vodikovih veza u konformacijama koje predstoje u otopini sintetiziranih peptida.

Abstract (english)

Boc-Ala-β-Alm (2, 81%), Ala-β-Alm (3, 47%), ferrocenecarboxylic acid (5, 53%), tert-butyl 1'-carboxy-1-ferrocenecarbamate (13, 93%) and ferrocene-1,1’-di(carbonyl chloride) (15, 86%) were prepared according to the described procedures. The reaction of 5 and 13 with Ala-β-Alm 3 in the presence of EDC and HOBt gave (N-ferrocenoyl-Ala)-β-Alm (6, 40%) and Boc-Fca-Ala-β-Alm (14, 49%), resp. Coupling of 5 with Ala-β-Alm 3 in the presence of Et3N gave Fn(CO-Ala-β-Alm)2 (16, 25%). The structure of β-lactam derivative 2 and ferrocene peptides 6, 14 i 16 was confirmed by spectral analysis (IR, 1H-NMR and 13C-NMR). The conformations population of the compounds prepared in solution, i.e. the strength of the incorporated hydrogen bonds was estimated on the basis of 1H-NMR and IR spectral analysis.

• Keywords: EDC/ HOBt-postupak; ferocenski peptidi; intramolekulske vodikove veze; β-laktam
• Keywords (english): EDC/HOBt-protocol; ferrocene peptides; intramolecular hydrogen Bonds; β-lactam
• Language: croatian
• URN:NBN: urn:nbn:hr:159:945403
• Study programme: Title: Food Technology; specializations in: Food Engineering; Course: Food Engineering; Study programme type: university; Study level: graduate; Academic / professional title: diplomirani inženjer prehrambene tehnologije; smjer prehrambeno inženjerstvo (diplomirani inženjer prehrambene tehnologije; smjer prehrambeno inženjerstvo)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-09-06 08:30:16