prikaz prve stranice dokumenta Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina
Embargo period 2025-12-15
master's thesis
Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina
Zagreb: University of Zagreb, Faculty of Science, 2023. urn:nbn:hr:217:456767
Kučas, Filip
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Kučas, F. (2023). Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:456767

Kučas, Filip. "Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina." Master's thesis, University of Zagreb, Faculty of Science, 2023. https://urn.nsk.hr/urn:nbn:hr:217:456767

Kučas, Filip. "Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina." Master's thesis, University of Zagreb, Faculty of Science, 2023. https://urn.nsk.hr/urn:nbn:hr:217:456767

Kučas, F. (2023). 'Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina', Master's thesis, University of Zagreb, Faculty of Science, accessed 22 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:456767

Kučas F. Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2023 [cited 2024 November 22] Available at: https://urn.nsk.hr/urn:nbn:hr:217:456767

F. Kučas, "Priprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2023. Available at: https://urn.nsk.hr/urn:nbn:hr:217:456767

Metadata
TitlePriprava derivata manoziliranog desmuramil-peptida s ferocenskom podjedinicom na α-položaju D-izoglutamina
Title (english)Synthesis of mannosylated desmuramyl peptide derivatives with a ferrocene subunit at α-position od D-isoglutamine
AuthorFilip Kučas
MentorVesna Petrović Peroković (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberDominik Cinčić (član povjerenstva)
Committee memberGordan Horvat (član povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2023-12-15, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu ovog diplomskog rada sintetizirana su tri nova manozilirana derivata desmuramil- peptida (DMP-a) s lipofilnom ferocenskom podjedinicom vezanom na α-kraj D-izoglutamina pri čemu je varirana duljina ugljikovodične razmaknice između ferocena i peptidnog dijela molekule. Aminoferocen je pripravljen uklanjanjem Boc-zaštitne skupine sa zaštićenog aminoferocena, dok su aminometilferocen i (2-aminoetil)ferocen pripravljeni redukcijom pripadnog amida, odnosno nitrila. Kao polazni peptid korišten je zaštićeni dipeptid L-alanil-D- glutaminska kiselina (Boc-L-Ala-D-Glu(OBn)). Na α-kraj glutaminske kiseline DMP-a amidnom vezom vezani su ferocenski amini s različitim brojem metilenskih skupina između amino-skupine i ferocenske podjedinice reakcijom kondenzacije pomoću EDC/HOBt i HBTU metode. Nakon uklanjanja Boc-zaštitne skupine s amino-skupine L-alanina u kiselim uvjetima, amidni ferocenski derivati desmuramil-peptida vezani su amidnom vezom s benzilima zaštićenom manoznom podjedinicom preko C2 razmaknice u istim uvjetima amidacije. Posljednji korak u sintezi bio je uklanjanje benzilnih zaštitnih skupina sa šećernog dijela molekule i benzilog estera s bočnog ogranka D-izoglutamina postupkom katalitičke hidrogenolize čime su uspješno sintetizirane ciljne molekule kojima se ispituje adjuvantski učinak.
Abstract (english)
In this diploma thesis, three new mannosylated derivatives of desmuramyl-peptide (DMP) were synthesized with a lipophilic ferrocene subunit bonded to the α-end of D-isoglutamine, whereby the length of the hydrocarbon spacer between ferrocene and the peptide part of the molecule was varied. Aminoferrocene was prepared by removing the Boc-protecting group from protected aminoferrocene, while aminomethylferrocene and (2-aminoethyl)ferrocene were prepared by reduction of the corresponding amide and nitrile. The protected dipeptide L-alanyl- D-glutamic acid (Boc-L-Ala-D-Glu(OBn)) was used as starting peptide. Ferrocene amines with a different number of methylene groups between the amino group and the ferrocene subunit are attached to the α-end of the glutamic acid of DMP via amide bond obtained by condensation reaction using EDC/HOBt and HBTU methods. After removal of the Boc-protecting group from the amino group of L-alanine under acidic conditions, amide ferrocene derivatives of desmuramyl-peptide are bound by an amide bond with benzylated mannose subunit via the C2 spacer under the same amidation conditions. The last step in the synthesis was the removal of the benzyl protecting groups from the sugar part of the molecule and the benzylic ester from the D-isoglutamine side branch by the catalytic hydrogenolysis process in the end target molecules were successfully obtained and where then tested for adjuvant activity.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:456767
ProjectNumber: IP-2020-02-9162
Title: Ferocenski analozi biomolekula: strukturna karakterizacija i biološka evaluacija
Title: Ferrocene analogues of biomolecules: structural characterization and biological evaluation
Acronym: FER-AN-BIOMOL
Leader: Lidija Barišić
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Graduate university studies in chemistry; specializations in: Graduate university studies in chemistry
Course: Graduate university studies in chemistry
Study programme type: university
Study level: graduate
Academic / professional title: sveučilišni/a magistar/magistra kemije (sveučilišni/a magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsEmbargoed access
Embargo expiration date: 2025-12-15
Terms of useLicence In copyright icon
Created on2024-01-10 10:55:01