Utjecaj ferocenske osnove na konformaciju peptidomimetika izvedenih iz leucina

undergraduate thesis

• Title (english): Influence of ferrocene templates on the conformation of peptidomimetics derived from leucine
• Author: Emanuela Krpan
• 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: 2023-07-05, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Nutrition

Abstract

Zbog njihovih nepovoljnih svojstava, upotreba peptida kao lijekova je ograničena. Iz tog se razloga u terapetuske svrhe upotrebljavaju peptidomimetici. Peptidomimetici su molekule čija je svrha oponašanje osnovnih motiva sekundarnih struktura peptida, a mogu se pripraviti umetanjem 1,1-' disupstituiranog ferocenskog kalupa u peptidnu sekvencu s ciljem uvođenja okreta. Ferocen je spoj, koji se sastoji od željezova kationa smještenog između dvije ciklopentadienilne jedinice. Zahvaljujući udaljenosti između ciklopentadienilnih jedinica, od 3,3 Å, omogućeno je nastajanje intramolekulskih vodikovih veza između peptidnih lanaca vezanih na ferocensku jezgru. Nastale vodikove veze, uzrokuju stvaranje struktura, nalik β-nabranim pločama. Tijekom izrade ovog rada, sinetetiziran je peptid 1, Ac-L-Ala-NH1-Fn-NH²-L-Leu-Boc, izveden iz ferocen-1,1 '-diamina i L-leucina. Korištenjem spektrometrijskih tehnika, infracrvene spektrometrije te nuklearne magnetske rezonancije, provedena je spektrometrijska analiza peptida 1, s ciljem proučavanja karaktera nastalih vodikovih veza. Dokazano je da NH-skupine vezane za ferocensku jezgru, sudjeluju u intramolekulskim vodikovim vezama.

Abstract (english)

Because of their unfavourable properties, the use of peptides as drugs is limited. For this reason, peptidomimetics are used for therapeutic purposes. Peptidomimetics are molecules whose purpose is to mimic the basic motifs of the secondary structures of peptides. They can be prepared by inserting a 1,1-' disubstituted ferrocene template into the peptide sequence with the aim of generating turns. Ferrocene is a compound consisting of an iron cation sandwiched between two cyclopentadienyl units. The distance between the cyclopentadienyl units, of 3.3 Å, allows the formation of intramolecular hydrogen bonds between the peptide chains attached to the ferrocene core. The resulting hydrogen bonds lead to the formation of structures, resembling β- sheets.
This paper describes the synthesis of peptide 1, Ac-L-Ala-NH1-Fn-NH²-L-Leu-Boc, derived from ferrocene-1,1'-diamine and L-leucine. Using spectrometric techniques, infrared spectrometry and nuclear magnetic resonance, a spectroscopic analysis of peptide 1 was performed to investigate the character of the formed hydrogen bonds. NH-groups attached to the ferrocene core were shown to participate in intramolecular hydrogen bonding.

• Keywords: peptidomimetici; ferocen; leucin; vodikove veze; IR- i NMR-spektrometrija
• Keywords (english): peptidomimetics; ferrocene; leucine; hydrogen bonds; IR- and NMR-spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:159:854151
• Study programme: Title: Nutrition; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) nutricionizma (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) nutricionizma)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-07-18 10:37:11