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doctoral thesis
Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena
Zagreb: University of Zagreb, Faculty of Science, 2021. urn:nbn:hr:217:278070
Nuskol, Marko
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Nuskol, M. (2021). Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:278070

Nuskol, Marko. "Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena." Doctoral thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:278070

Nuskol, Marko. "Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena." Doctoral thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:278070

Nuskol, M. (2021). 'Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 26 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:278070

Nuskol M. Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 November 26] Available at: https://urn.nsk.hr/urn:nbn:hr:217:278070

M. Nuskol, "Priprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:217:278070

Metadata
TitlePriprava, konformacijska analiza i kirooptička svojstva peptidnih derivata aminoferocena
Title (english)Synthesis, conformational analysis and chiroptical properties of peptide derivatives of aminoferrocene
AuthorMarko Nuskol
MentorMojca Čakić Semenčić (mentor)
Committee memberIvan Kodrin (predsjednik povjerenstva)
Committee memberPredrag Novak (član povjerenstva)
Committee memberLidija Barišić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2021-01-07, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
U okviru ove doktorske disertacije provedena je sinteza i konformacijska analiza peptidnih konjugata aminoferocena [Boc–(AA)n–NH–Fc, Fc = ferocenil, AA = D(L)–Pro, D(L)–Ala, Boc (tert–butoksikarbonil), Aib (α–aminoizobutirična kiselina), n = 2–4] kao i dinuklearnih ferocenskih derivata [Fc–CO–(AA)2–NH–Fc, AA = D(L)–Pro, D(L)–Ala] kako bi se istražio utjecaj nabiranja aminokiselinskog slijeda na kirooptička svojstva organometalnog kromofora. Konformacijskom analizom (IR–spektroskopija, spektroskopija NMR i CD, kristalografska analiza, računalno modeliranje) utvrđeno je da su pripravljeni spojevi, u otopini i u čvrstom stanju, stabilizirani unutarmolekulskim vodikovim vezama koje podržavaju okrete i uzvojnice slične onima u prirodnim peptidima. Kombiniranim teorijskim i eksperimentalnim pristupom pokazano je kako kiralno uređenje peptidnog segmenta inducira Cottonov efekt u blizini UV/Vis apsorpcijskog maksimuma ferocena čiji je predznak u korelaciji s diedarskim kutom koji opisuje rotaciju oko veze između ferocenskog kromofora i peptidnog segmenta.
Abstract (english)
In this PhD thesis peptide derivatives of aminoferrocene [Boc–(AA)n–NH–Fc, Fc = ferrocenyl, AA = D(L)–Pro, D(L)–Ala, Aib, Boc (tert–butoxycarbonyl), Aib (α– aminoisobutyric acid), n = 2–4] as well as the dinuclear ferrocene derivatives [Fc–CO– (AA)2–NH–Fc, AA = D(L)–Pro, D(L)–Ala] were synthesized. The novel compounds were subjected to conformational analysis in order to investigate the influence of folding of amino acid sequence on the chiroptical properties of organometallic chromophore. Conformational analysis (IR, NMR, and CD spectroscopy, crystallographic analysis, computational modeling) of the prepared compounds revealed that they are stabilized by intramolecular hydrogen bonds, that support turns and helices similar to those in natural peptides, in solution as well as in solid state. The combined theoretical and experimental approach has shown that the chiral arrangement of the peptide segment induces Cotton effect near the UV/Vis absorption maximum of ferrocene, whose sign is in correlation with dihedral angle which describes rotation around ferrocene–peptide linkage.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:278070
Promotion2021
Study programmeTitle: Doctoral study in chemistry
Study programme type: university
Study level: postgraduate
Academic / professional title: doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija (doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija)
Type of resourceText
Extent175 str. ; 30 cm
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2021-02-26 14:19:27