Utjecaj zaštitnih skupina i kiralnosti aminokiselina na konformaciju ferocenskih tripeptida Fn-Pro-Ala

undergraduate thesis

• Title (english): Impact of protecting groups and chirality of amino acids on the conformation of ferrocene tripeptides Fn-Pro-Ala
• Author: Antonio Damjanović
• Mentor: Monika Kovačević (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: 2022-09-19, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Strukturne različitosti aminokiselina, a samim time i peptida te proteina, omogućuju brojne biološki važne funkcije proteina u stanici. Budući da je mogućnost korištenja peptida i proteina u terapeutske svrhe ograničena, njihova svojstva moguće je poboljšati ugradnjom ferocenskog kalupa u strukturu peptida, što omogućuje tvorbu vodikove veze između peptidnih lanaca kao glavni preduvjet za tvorbu sekundarnih struktura, a samim time i za biološku aktivnost i funkciju peptida.
U ovom je radu opisana sinteza i konformacijska analiza tripeptida 2 i 3 (Boc-L(D)-Ala-D-Pro-NH-Fn-COOMe) te 4 i 5 (Ac-L(D)-Ala-D-Pro-NH-Fn-COOMe), izvedenih iz 1ʼ-aminoferocen-1-karboksilne kiseline (Fca) i Pro-Ala peptidne sekvence. Provedena je IR-, NMR- i CD-spektroskopska analiza dobivenih biokonjugata, s ciljem ispitivanja utjecaja kiralnosti i zaštitnih skupina (Boc/Ac) aminokiselina na mogućnost tvorbe intramolekulskih vodikovih veza te u konačnici i sekundarnih peptidnih struktura

Abstract (english)

The structural differences of amino acids, and consequently of peptides and proteins, enable numerous biologically important functions of proteins in the cell. Since the possibility of using peptides and proteins for therapeutic purposes is limited, their properties can be improved by incorporating certain ferrocene templates into the peptide structure. Formation of hydrogen bond is main prerequisite for the formation of secondary structures, and thus for the biological activity and function of the peptides.
This paper describes the synthesis and conformational analysis of tripeptides 2 and 3 (Boc-L(D)-Ala-D-Pro-NH-Fn-COOMe), as well as the tripeptides 4 and 5 (Ac-L(D)-Ala-D-Pro-NH-Fn-COOMe), derived from 1ʼ-aminoferrocene-1-carboxylic acid (Fca) and Pro-Ala peptide sequence. IR-, NMR- and CD-spectroscopic analysis of the obtained bioconjugates was carried out, with the aim of examining the influence of chirality and protective groups (Boc/Ac) of amino acids on the possibility of intramolecular hydrogen bond formation, and ultimately secondary peptide structures.

• Keywords: ferocen; konformacijska analiza; prolin; alanin; vodikova veza
• Keywords (english): ferrocene; conformational analysis; proline; alanine; hydrogen bond
• Language: croatian
• URN:NBN: urn:nbn:hr:159:354837
• Study programme: Title: Biotechnology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-06-07 07:54:03