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master's thesis
Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina
Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology, 2020. urn:nbn:hr:159:063241
Stipčić, Tea
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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Stipčić, T. (2020). Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina (Master's thesis). Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:159:063241

Stipčić, Tea. "Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina." Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, 2020. https://urn.nsk.hr/urn:nbn:hr:159:063241

Stipčić, Tea. "Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina." Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, 2020. https://urn.nsk.hr/urn:nbn:hr:159:063241

Stipčić, T. (2020). 'Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina', Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:159:063241

Stipčić T. Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina [Master's thesis]. Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology; 2020 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:159:063241

T. Stipčić, "Priprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina", Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, Zagreb, 2020. Available at: https://urn.nsk.hr/urn:nbn:hr:159:063241

Metadata
TitlePriprava i konformacijska analiza ferocenskih tripeptida Ala-Pro sekvence izvedenih iz ferocen-1,1'-diamina
Title (english)Synthesis and conformational analysis of ferrocene tripeptides derived from ferrocene-1,1'-diamine and Ala-Pro sequence
AuthorTea Stipčić
MentorMonika Kovačević (mentor)
Committee memberLidija Barišić (predsjednik povjerenstva)
GranterUniversity of Zagreb
Faculty of Food Technology and Biotechnology
(Department of Chemistry and Biochemistry)
(Laboratory for Organic Chemistry)
Zagreb
Defense date and country2020-07-16, Croatia
Scientific / art field,
discipline and subdiscipline		BIOTECHNICAL SCIENCES
Nutrition
Abstract
Biološka primjena prirodnih peptida ograničena je njihovim nepoželjnim svojstvima (konformacijska fleksibilnost, niska stabilnost) zbog čega se intenzivno istražuje područje peptidomimetika. Ferocenski konjugati s aminokiselinama često se koriste kao peptidomimetici jer su se 1, n-disupstituirani ferocenski biokonjugati pokazali dobrim kalupom za tvorbu intramolekulskih vodikovih veza. Sekvence bogate alaninom i prolinom pokazuju brojna poželjna svojstva (visoka topljivost, stabilnost i biodostupnost), dok ferocenski diamin inducira tvorbu intramolekulskih vodikovih veza koje su stabilizirane 14-članim prstenovima. U ovom Diplomskom radu opisana je sinteza i konformacijska analiza ferocenskih tripeptida 12-15 [Ac-L(D)-Ala-D-Pro-NH-Fn-NH-L(D)-Pro-Boc, Fn = ferocenilen, Ac = acetil, Boc = tert-butoksikarbonil] kao i njihovih prekursora 2-5 [Boc(Ac)-L(D)-Ala-D-Pro-NH-Fca-COOMe], izvedenih iz ferocen-1,1'-diamina i peptidne sekvence Ala-Pro. Utjecaj kiralnosti pojedinih aminokiselina u peptidnom lancu, kao i N-terminalnih zaštitnih skupina (Boc, Ac) ispitani su spektroskopskom analizom (IR-, NMR- i CD-spektroskopija) te potkrijepljeni DFT-računima. Pokazalo se da promjenom kiralnosti aminokiselina dolazi do promjene u obrascima vodikovih veza, dok zaštitne skupine nemaju utjecaj na tvorbu istih.
Abstract (english)
The biological application of natural peptides is limited by their undesirable properties (conformational flexibility, low stability), therefore the field of peptidomimetics is being intensively investigated. As the 1, n-disubstituted ferrocene bioconjugates have been established as good motif for the formation of intramolecular hydrogen bonds, ferrocene conjugates with amino acids are often used as peptidomimetics. Regarding to that alanine- and proline-rich sequences exhibit a number of desirable properties (high solubility, stability, and bioavailability), as well as the ferrocene diamine induces the formation of intramolecular hydrogen bonds that are stabilized by forming 14-membered rings we have decided to prepare new type of peptidomimetics. This Graduate Thesis describes the synthesis and conformational analysis of ferrocene tripeptides 12-15 [Ac-L(D)-Ala-D-Pro-NH-Fn-NH-L(D)-Pro-Boc, Fn = ferrocenylene, Ac = acetyl, Boc = tert-butoxycarbonyl] as well as their precursors 2-5 [Boc(Ac)-L(D)-Ala-D-Pro-NH-Fca-COOMe], derived from ferrocene-1,1'-diamine and Ala-Pro peptide sequences. The influence of chirality of individual amino acids in the peptide chain, as well as N-terminal protecting groups (Boc, Ac) were examined by spectroscopic analysis (IR-, NMR- and CD-spectroscopy) and supported by DFT-calculations. It has been shown that change in the chirality of amino acids leads to change in the hydrogen bond patterns, while the protecting groups have no effect on their formation.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:159:063241
Study programmeTitle: Nutrition
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra nutricionizma (magistar/magistra nutricionizma)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence Attribution-NonCommercial-NoDerivs 3.0 Unported (CC BY-NC-ND 3.0) icon
Created on2020-07-20 12:12:21