Priprava i konformacijska analiza ferocenskih dipeptida izvedenih iz ferocen-1,1'-diamina s aminokiselinama leucinom i alaninom

master's thesis

• Title (english): Preparation and conformational analysis of ferrocene dipeptides derived from ferrocene-1,1'-diamine with leucine and alanine amino acids
• Author: Maj Mezić
• 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: 2024-07-04, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Sintetski peptidi, odnosno peptidomimetici, sadrže strukturne značajke kojima se prevladavaju ograničenja prirodnih peptida. Oponašanje sekundarne strukture prirodnih peptida jedan je od mogućih pristupa u dizajnu peptidomimetika. Peptidomimetici na bazi ferocena imaju mogućnost zauzimanja sekundarnih strukturnih elemenata nakon inkorporiranja različitih aminokiselina, ovisno o njihovu kiralnosti i steričkim svojstvima C- i N- zaštitnih skupina. Cilj ovog diplomskog rada bio je opisati sintezu i prikazati konformacijsku analizu biokonjugata Ac–D– Ala–NH–Fn–NH–L/D–Leu–Boc (6 i 7), dobivenih iz ferocen-1,1'-diamina i aminokiselina leucina i valina. Korištenjem različitih spektroskopskih metoda (IR-, NMR- i CD-spektroskopija) ispitivao se utjecaj kiralnosti leucina na strukturu sintetiziranog dipeptida. Rezultati su pokazali kako konformacijski prostor homokiralnog dipeptida Ac–D–Ala–NH–Fn–NH–D–Leu–Boc (7) odgovara prije pripravljenim konjugatima Ac–L–Ala–NH–Fn–NH–L–Ala–Boc (VIII) i Ac–D–Leu–NH–Fn–NH–D–Leu–Boc (XI). Uz to, utvrđeni su nepromijenjeni obrasci vodikovih veza nakon zamjene aminokiselina leucinom.

Abstract (english)

Synthetic peptides, also known as peptidomimetics, have structural features that overcome the limitations of natural peptides. Mimicking the secondary structure of natural peptides is one of the possible approaches for the developement of peptidomimetics. Ferrocene-based peptidomimetics have the ability to adopt secondary structure elements after the incorporation of different amino acids, depending on their chirality and the steric properties of the C- and N- protecting groups. The aim of this work was to describe the synthesis and present the conformational analysis of the bioconjugates Ac–D–Ala–NH–Fn–NH–L/D–Leu–Boc (6 and 7), obtained from ferrocene-1,1'-diamine and the amino acids leucine and valine. Various spectroscopic methods (IR, NMR, and CD spectroscopy) were used to investigate, the influence of the chirality of leucine on the structure of the synthesized dipeptides. The results showed that the conformational space of the homochiral dipeptide Ac–D–Ala–NH–Fn–NH–D–Leu–Boc (7) corresponds to the previously prepared conjugates Ac–L–Ala– NH–Fn–NH–L–Ala–Boc (VIII) and Ac–D–Leu–NH–Fn–NH–D–Leu–Boc (XI). In addition, unchanged hydrogen bonding patterns were observed after replacement of the amino acids with leucine.

• Keywords: ferocen; sekundarna struktura; leucin; peptidomimetici; konformacijska analiza
• Keywords (english): ferrocene; secondary structure; leucine; peptidomimetics; conformational analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:897120
• 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: 2024-10-30 13:25:13