Priprava neprirodnih C-glikozilnih aminokiselina

master's thesis

• Title (english): Synthesis of non-natural C-glycosyl amino acids
• Author: Magdalena Surko
• Mentor: Dragana Vuk (mentor)
• Mentor: Ivanka Jerić (komentor)
• Committee member: Dragana Vuk (predsjednik povjerenstva)
• Committee member: Marijana Kraljić Roković (član povjerenstva)
• Committee member: Ivanka Jerić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-09-17, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Peptidi i proteini imaju ključnu ulogu u nizu bioloških i fizioloških procesa. Unatoč velikoj raznolikosti u biološkoj funkciji i strukturi, njihova upotreba kao terapeutika ograničena je lošom stabilnošću i bioraspoloživošću. Potreba za kontrolom funkcije peptida dovela je do razvoja peptidomimetika, spojeva koji mogu oponašati sekundarne strukture proteina, a time i njihove funkcije. Samostrukturne organizacije poput okreta, spirala, listova i petlji mogu se dobiti kemijskim modifikacijama pojedinih aminokiselina ili peptida. Njihova strukturna i konformacijska analiza omogućuje stvaranje biblioteke spojeva opisanih svojstava, što je od velike važnosti za farmaceutsku industriju i znanost o materijalima. Cilj istraživanja ovog diplomskog rada je sinteza dipeptida s ugrađenom neprirodnom C-glikozilnom aminokiselinom. Za dobivanje C-glikozilne jedinice korištena je trokomponentna Passerinijeva reakcija, gdje je kao aldehidna komponentna korišten izopropilidenima zaštićen derivat sorboze. Passerinijev produkt je dobiven u visokom prinosu i diastereoselektivnosti. Post-kondenzacijske modifikacije Passerinijevog produkta dale su odgovarajući dipeptidni derivat C-glikozilne aminokiseline. Izolacija i pročišćavanje novopripravljenih organskih spojeva provedeno je primjenom kromatografskih metoda. Također, identifikacija i strukturna karakterizacija novih produkata provedena je različitim spektroskopskim metodama.

Abstract (english)

Peptides and proteins have a crucial role in a number of biological and physiological process. Despite their enormous diversity in biological function and structure, their use as therapeutics is limited by poor stability and bioavailability. The need to control the functions of natural peptides has led to the development of peptidomimectics, compounds that can mimic secondary protein structures, as well as their functions. Self-structural organizations such as turns, helices, sheets and loops can be accessed by chemical modifications of amino acids or peptides. In-depth structural and conformational analysis offer a way to establish peptidomimetic libraries which is of great importance for the pharmacology and material science. The objective of the research proposed in this master thesis is the synthesis of a dipeptide with an incorporated C-glycosyl amino acid. The C-glycosyl unit was installed by the Passerini reaction comprising isopropylidene-protected sorbose-derived aldehyde component. The Passerini product was obtained in high yield and diastereoselectivity. Post-condensation modifications of the Passerini product gave the corresponding dipeptide with incorporated C-glycosyl amino acid. Isolation and purification of newly prepared organic compounds was carried out using chromatographic methods. Also, new products were identified and structurally characterized was by various spectroscopic methods.

• Keywords: neprirodne aminokiseline; ugljikohidrati; C-glikozilne aminokiseline; Passserinijeva reakcija
• Keywords (english): non-natural amino acids; carbohydrates; C-glycosyl amino acids; Passerini reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:265697
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Closed access
• Created on: 2023-04-14 10:16:26