Priprava i konformacijska analiza ferocenskih dipeptida pripravljenih iz ferocen-1,1'-diamina s valinom i alaninom

master's thesis

• Title (english): Synthesis and conformational analysis of ferrocene dipeptides derived from ferrocene-1,1'-diamine with valine and alanine
• Author: Nikolina Orešković
• Mentor: Monika Kovačević (mentor)
• Committee member: Lidija Barišić (predsjednik povjerenstva)
• Committee member: Anita Horvatić (član povjerenstva)
• Committee member: Antonela Ninčević Grassino (član povjerenstva)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2024-02-06, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Da bi se postigla željena biološka aktivnost sintetski pripravljenih peptida, nekoliko je važnih uvjeta koje takvi peptidi moraju zadovoljiti: hidrofobnost, neto naboj, amfipatski karakter i sekundarna struktura. Sekundarna struktura peptidomimetika, dobivenih iz ferocena, može se prilagoditi brojem i vrstom aminokiselina iz kojih je pripravljen, modificiranjem njihove kiralnosti i steričke kompleksnosti C- i N-zaštitnih skupina, počevši od odabira ferocenske osnove: ferocenske aminokiseline [(Fca), -OCFn-NH-] ili simetrično disupstituirane ferocenske dikiseline [(Fcd), -OC-Fn-CO-] i diamina [(Fcda), - NH-Fn-NH-]. U sklopu ovog diplomskog rada pripravljeni su ferocenski biokonjugati iz ferocen-1,1'-diamina i aminokiselina alanina i valina (Ac-D-Ala-NH-Fn-NH-L/D-Val-Boc). Utjecaj kiralnosti valina, kao i zamjena alanina sa sterički zahtjevnijim valinom ispitani su spektroskopskom analizom (IR-, NMR- i CD-spektroskopija). Pokazalo se da heterokiralni analog (Ac-D-Ala-NH-Fn-NH-L-Val-Boc) nije moguće pripraviti u količini potrebnoj za konformacijsku analizu, dok konformacijski prostor homokiralnog analoga (Ac-D-Ala-NH-Fn-NH-D-Val-Boc) odgovara prije pripravljenim konjugatima s alaninom, odnosno valinom. Zaključeno je da uvođenjem valina ne dolazi do promjene u obrascima vodikovih veza.

Abstract (english)

In order to achieve the desired biological activity of synthetically prepared peptides, these peptides must fulfill several important conditions: hydrophobicity, net charge, amphipathic character and secondary structure. The secondary structure of peptidomimetics derived from ferrocene can be adjusted by the number and type of amino acids from which they are prepared, by changing their chirality and the steric complexity of the C- and N-protecting groups, starting with the selection of the ferrocene base: ferrocene amino acids [(Fca), -OC-Fn- NH-] or symmetrically disubstituted ferrocene diacid [(Fcd), - OC-Fn-CO-] and diamine [(Fcda), -NH-Fn-NH-]. In this work, ferrocene bioconjugates were prepared from ferrocene-1,1'-diamine and the amino acids alanine and valine (Ac-D-Ala-NH-Fn-NH-L/D-Val-Boc). The influence of valine chirality and the replacement of alanine by the sterically more demanding valine, were examined by spectroscopic analyses (IR, NMR and CD spectroscopy). It was found that the heterochiral analogue (Ac-D-Ala-NHFn-NH-L-Val-Boc) can not be prepared in the amount required for conformational analysis, whereas the conformational space of the homochiral analogue (Ac-D-Ala-NH-Fn-NH-D-Val-Boc) corresponds to the previously prepared conjugates with alanine or valine. It was found that the introduction of valine does not alter the hydrogen bonding patterns.

• Keywords: peptidomimetik; ferocen; konformacijska analiza; valin; alanin
• Keywords (english): peptidomimetic; ferrocene; conformational analysis; valine; alanine
• Language: croatian
• URN:NBN: urn:nbn:hr:159:661428
• Study programme: Title: Molecular Biotechnology; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka molekularne biotehnologije (magistar/magistra inženjer/inženjerka molekularne biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-07-24 11:56:12