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undergraduate thesis
Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza
Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology, 2019. urn:nbn:hr:159:942498
Ivančić, Marina
University of Zagreb
Faculty of Food Technology and Biotechnology
Department of Chemistry and Biochemistry
Laboratory for Organic Chemistry

Institutional repository: Repository of the Faculty of Food Technology and Biotechnology

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Ivančić, M. (2019). Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:159:942498

Ivančić, Marina. "Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza." Undergraduate thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, 2019. https://urn.nsk.hr/urn:nbn:hr:159:942498

Ivančić, Marina. "Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza." Undergraduate thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, 2019. https://urn.nsk.hr/urn:nbn:hr:159:942498

Ivančić, M. (2019). 'Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza', Undergraduate thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, accessed 17 July 2024, https://urn.nsk.hr/urn:nbn:hr:159:942498

Ivančić M. Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology; 2019 [cited 2024 July 17] Available at: https://urn.nsk.hr/urn:nbn:hr:159:942498

M. Ivančić, "Biokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza", Undergraduate thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, Zagreb, 2019. Available at: https://urn.nsk.hr/urn:nbn:hr:159:942498

Metadata
TitleBiokonjugati ferocenske aminokiseline s dipeptidom Pro-Ala: sinteza i konformacijska analiza
Title (english)Bioconjugates of ferroceneaminoacid with dipeptide Pro Ala: synthesis and conformational analysis
AuthorMarina Ivančić
MentorLidija Barišić (mentor)
GranterUniversity of Zagreb
Faculty of Food Technology and Biotechnology
(Department of Chemistry and Biochemistry)
(Laboratory for Organic Chemistry)
Zagreb
Defense date and country2019-07-15, Croatia
Scientific / art field,
discipline and subdiscipline		BIOTECHNICAL SCIENCES
Food Technology
Abstract
Najveći izazov u peptidomimetici predstavlja modifikacija strukture prirodnih peptida i dizajn odgovarajućih peptidomimetika s ciljem unapređenja njihovog biološkog učinka i prevladavanja ograničenosti terapeutske primjene. U ovom radu opisana je sinteza i konformacijska analiza tripeptida Boc-L-Pro-L-Ala-NH-Fn-COOMe (Fn = 1,1'-ferocenilen), nastalog kopuliranjem 1'-aminoferocen-1-karboksilne kiseline (Fca) s homokiralnom Pro-Ala sekvencom. Cilj rada bio je ispitati utjecaj slijeda, kiralnosti i bočnog ogranka prirodnih aminokiselina (Pro i Ala) kao i potencijal Fca u indukciji elemenata sekundarne peptidne strukture. Sintetizirani tripeptid podvrgnut je strukturnoj analizi primjenom IR-, NMR- (ovisnim o koncentraciji, temperaturi i otapalu) i CD- spektroskopije, u svrhu utvrđivanja njegovog konformacijskog prostora koji je ključan za potencijalni farmakološki učinak. Prema rezultatima analize, osobitost pripravljenog biokonjugata jest dominacija intramolekulskih vodikovih veza srednje jakosti koje doprinose stabilizaciji molekule, odnosno induciraju tvorbu 7- članih i 10-članih IHB-prstenova (IHB, engl. Intramolecular Hydrogen Bond), odnosno γ-i β-okreta u peptidnom lancu.
Abstract (english)
The greatest challenge in the field of peptidomimetic chemistry is the modification of the structure of natural peptides and the design of appropriate peptidomimetics with the aim of enhancing their biological effect and overcoming the limitation of therapeutic application. This study has explored the synthesis and conformational analysis of Boc-L-Pro-L-Ala-NH-Fn-COOMe (Fn = 1,1'-ferrocenilene) tripeptide obtained by copulation of 1'-aminoferrocene-1-carboxylic acid (Fca) with homochiral Pro – Ala sequence. The main goal of this study was to explore the influence of the sequence, chirality and side chain of natural amino acids (Pro and Ala) as well as the potential of Fca in the induction of secondary peptide structure elements. The synthesized tripeptide was subjected to detail structural analysis by IR, NMR (concentration-, temperature- and solvent-dependent) and CD spectroscopy in order to determine its conformational space, which has a crucial impact on potential pharmacological effect. The obtained spectroscopic results revealed the predominance of intramolecular hydrogen bonds of medium strength that contribute to the stabilization of the compound by inducing the formation of 7- and 10-membered IHB-rings (IHB, Intramolecular Hydrogen Bond), i.e. γ- and β-turns within the peptide chain.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:159:942498
Study programmeTitle: Food Technology
Study programme type: university
Study level: undergraduate
Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
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Created on2019-07-17 11:38:21