Priprava ferocen-1,1'-diamina i njegovih konjugata s aminokiselinama

master's thesis

• Title (english): Preparation of ferrocene-1,1'-diamine and its conjugates with amino acids
• Author: Ivana Šimić
• 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: 2007-07-06, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

Do danas su pripravljeni i ispitani brojni konjugati ferocen-1,1’-dikarboksilne kiseline i prirodnih aminokiselina – Fn(COAA1-2OMe)2 [1]. Naša istraživačka grupa sintetizirala je različite bioorganometalne spojeve sastavljene od 1’-amino-1-karboksilnih kiselina i prirodnih aminokiselina, u namjeri ispitivanja djelovanja ferocenske podjedinice kao začetnika okreta uz nastajanje intramolekulskih vodikovih veza [2]. Simetrično disupstituirani biokonjugati ferocen-1,1’-diamina (Fnd) – Fn(NHAA1-2Boc)2 opisani su u samo jednom radu [3]. Naša istraživanja usmjerili smo prema nesimetrično supstituiranim biokonjugatima Fnd (13, 15, 17 i 19). tert-Butil-1'-acetamido-1-ferocenkarbamat (9) pripravljen je višestupanjskom sintezom dio kojih je prethodno opisan [2]. Biokonjugati Fnd 13, 15, 17 i 19 sintetizirani su reakcijom 9 i Boc-zaštićenih prirodnih aminokiselina koristeći EDC/HOBt-protokol. Konformacijska analiza pripravljenih spojeva načinjena je na osnovi IR-, NMR-vr- i CD-spektroskopije.

Abstract (english)

A number of conjugates of ferrocene-1,1’-dicarboxylic acid with natural amino acids – Fn(COAA1-2OMe)2 have been prepared and investigated so far [1]. Our research group synthesized various bioorganometallics composed from 1’-amino-1-carboxylic acid and natural amino acids, aiming to investigate the role of ferrocene subunit as turn inducer and to study the intramolecular hydrogen bonds formed [2]. Symmetrically disubstituted bioconjugates of ferrocene-1,1’-diamine (Fnd) – Fn(NHAA1-2Boc)2 are described in solely one paper [3]. We directed our research to unsymmetrically substituted bioconjugates of Fnd (13, 15, 17 i 19). tert-Butyl-1'-acetamido-1-ferrocenecarbamate (9) was synthesized by multistep reactions sequence using mostly the transformations similar to previously described [2]. Compounds 13, 15, 17 i 19 were prepared by reactions of 9 with Boc-protected natural amino acids using EDC/ HOBt protocol. Conformational analysis of the compounds prepared on the basis of IR, NMR-vr-, and CD-spectroscopy is presented.

• Keywords: aminokiseline; ferocen; intramolekulske vodikove veze; helična kiralnost; peptidi
• Keywords (english): amino acids; ferrocene. intramolecular hydorgen bonds; helical chirality; peptides
• Language: croatian
• URN:NBN: urn:nbn:hr:159:226134
• 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: 2017-09-07 09:57:55