Sinteza i strukturna karakterizacija konjugata metil 1-aminoferocen-1-karboksilata i dipeptida prolil-alanina

undergraduate thesis

• Title (english): Synthesis and structural characterization of methyl 1-aminoferrocene-1-carboxylate conjugates with prolyl-alanine dipeptide
• Author: Lucija Šimunović
• Mentor: Lidija Barišić (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: 2022-09-16, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

Peptidomimetici u odnosu na prirodne peptide formiraju rigidniju strukturu i daleko su konformacijski i proteolitički stabilniji, što im omogućuje primjenu u dizajnu i sintezi lijekova i biološki aktivnih spo-jeva. „Zaključavanje“ peptidomimetika u stabilnu bioaktivnu konformaciju alfa-uzvojnice, beta-ploče ili okreta smanjuje mogućnost interakcija s neželjenim receptorima u ljudskom organizmu umanjujući tako vjerojatnost nuspojava koje se nerijetko javljaju kod peptidnih lijekova. Budući da peptidomimetici preko svojih „hot-spot“ regija stupaju u interakcije s receptorima zahvaljujući komplementarnosti nji-hovih 3D struktura, njihov se dizajn zasniva na oponašanju sekundarnih strukturnih elemenata prisutnih u „hot-spot“ regijama. Poznati začetnik okretâ, metil 1'-aminoferocen-1-karboksilat, u ovom je završ-nom radu primjenom EDC/ HOBt metode kopuliran s homo- i/ili heterokiralnim Pro-Ala dipeptidima, a struktura nastalih biokonjugata 3-6 potvrđena je IR- i NMR-spektroskopijom.

Abstract (english)

Compared to the natural peptide, peptidomimetics form a rigid structure and are much more stable in terms of conformational flexibility and proteolytic activity, which allows their use in the design and synthesis of drugs and biologically active compounds. "Locking" peptidomimetics into a stable bioac-tive conformation of alpha-helix, beta-sheet or turn reduces the possibility of interaction with undesired re-ceptors in the human body, thereby reducing the likelihood of side effects that are common with peptide drugs. Since peptidomimetics interact with receptors through their "hot-spot" regions thanks to the com-plementarity of their 3D structure, their design is based on mimicking the secondary structural elements present in the "hot-spot" regions. The well-described turn inducer, methyl 1'-aminoferrocene-1-carbox-ylate, was coupled with homo- and/or heterochiral Pro-Ala dipeptides using the EDC/ HOBt method, and the structure of the resulting bioconjugates 3-6 was determined by IR and NMR spectroscopy.

• Keywords: ferocen; peptidi; strukturna karakterizacija; IR; NMR
• Keywords (english): ferrocene; peptides; structural characterization; IR; NMR
• Language: croatian
• URN:NBN: urn:nbn:hr:159:569644
• Study programme: Title: Food Technology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-06-07 07:51:03