Priprava i konformacijska analiza bis-ferocenskih peptida

master's thesis

• Title (english): Synthesis and conformational analysis of bis-ferrocene peptides
• Author: Bosiljka Studen
• Mentor: Mojca Čakić Semenčić (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Physical Chemistry and Corrosion); Zagreb
• Defense date and country: 2018-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Jednostavni konjugati aminoferocena i peptida mogu tvoriti uređene sekundarne strukturne elemente, a pritom homo- odnosno heterokiralnost aminokiselinske sekvencije uvjetuje tvorbu β- odnosno γ-okreta. U ovom radu opisana je priprava i konformacijska analiza homokiralnih bis-ferocenskih derivata VI [Fc-CO- L-Pro-L-Ala-NH-Fc; (8) i Fc-CO-D-Pro-D-Ala-NH-Fc; (9)]. Iscrpna spektroskopska analiza (CD-, IR-, 1H- i 2D NMR), u kombinaciji s molekulskim modeliranjem i kristalografskom analizom, pokazala je kako se u najstabilnijim konformacijama 8 i 9 javljaju, vodikovim vezama podržani, 10-člani prstenovi (β-okreti). Cottonovi efekti opaženi u blizini UV/Vis apsorpcijskog maksimuma ferocena u CD-spektrima 8 i 9 proizlaze iz prijenosa kiralne informacije iz lokalne sekundarne strukture do akiralnog ferocenskog kromofora.

Abstract (english)

Simple conjugates of aminoferocene and peptides are able to form ordered secondary structural elements, while homo- or heterocirality of the amino acid sequence determines the formation of β- or γ-turns. This thesis describes the synthesis and conformational analysis of homochiral bis-ferrocene derivatives VI [Fc-CO-L-Pro-L-Ala-NH-Fc; (8) and Fc-CO-D-Pro-D-Ala-NH-Fc; (9)]. Thorough spectroscopic analysis (CD-, IR-, 1H- and 2D NMR), in combination with molecular modelling and X-ray diffraction, revealed the presence of 10-membered rings (β-turns), supported by hydrogen bonds, in the most stable conformations of 8 and 9. Cotton effects observed near the UV/Vis absorption maximum of ferrocene in CD spectra of 8 and 9 originate from the transfer of chiral information from the local secondary structure to the achiral ferrocene chromophore.

• Keywords: Ferocen; peptidi; konformacijska analiza; NMR-spektroskopija; β-okret
• Keywords (english): Ferrocene; peptide; conformational analysis; NMR-spectroscopy; β-turn
• Language: croatian
• URN:NBN: urn:nbn:hr:159:520121
• 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: 2019-12-02 13:28:50