Sinteza i konformacijska analiza ferocenskih dipeptida izvedenih iz ferocen-1,1'-diamina s fenilalaninom i alaninom

master's thesis

• Title (english): Synthesis and conformational analysis of ferrocene dipeptides derived from ferrocene-1,1’-diamine with phenylalanine and alanine
• Author: Evelin Radešić
• 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: 2024-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Recentna znanstvena istraživanja pokazuju važnost ferocena kao začetnika okreta u peptidomimeticima, s obzirom da umetanje ferocenskog kalupa u peptide diktira usmjerenost peptidnog lanca i utječe na njegovu rigidnost, ovisno o obrascu uspostavljenih intramolekulskih vodikovih veza. Heteroanularno disupstituirani feroceni čiji su ciklopentadienilni prstenovi udaljeni oko 3,3 Å (što odgovara prosječnoj duljini vodikove veze), predstavljaju molekulske kalupe za indukciju okreta i struktura sličnih β-pločama, u njihovim konjugatima s prirodnim aminokiselinama. U ovom radu opisana je priprava homokiralnog dipeptida Ac−D−Ala−NH−Fn−NH− D−Phe−Boc (6) te utjecaj ferocenskog kalupa i kiralnosti peptidne okosnice na uspostavu intramolekulskih vodikovih veza. Strukturna i konformacijska analiza dipeptida 6 provedena je mjerenjem koncentracijski- i temperaturno-ovisnih IR i NMR spektara, CD-spektara te titracijom NMR i CD uzoraka s DMSO.

Abstract (english)

Recent scientific research highlights the importance of ferrocene as a turn inducer in peptidomimetics, as the incorporation of a ferrocene template into peptides dictates the orientation of the peptide chain and influences its rigidity, depending on the pattern of established intramolecular hydrogen bonds. Heteroannular disubstituted ferrocenes, whose cyclopentadienyl rings are approximately 3.3 Å apart (corresponding to the average length of a hydrogen bond), provide molecular templates for inducing turns and β-sheet-like structures in their conjugates with natural amino acids. This work describes the preparation of the homochiral dipeptide Ac–D–Ala–NH–Fn–NH– D–Phe–Boc (6) and the influence of the ferrocene template and the chirality of the peptide backbone on the establishment of intramolecular hydrogen bonds. The structural and conformational analysis of dipeptide 6 was performed by measuring concentration- and temperature-dependent IR and NMR spectra, CD spectra, and by titration of NMR and CD samples with DMSO.

• Keywords: ferocen; peptidomimetici; fenilalanin; alanin; konformacijska analiza
• Keywords (english): ferrocene; peptidomimetics; phenylalanine; alanine; conformational analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:118872
• 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: 2024-07-18 08:07:54