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master's thesis
Priprava ferocenskih estera manoziliranog desmuramil-dipeptida
Zagreb: University of Zagreb, Faculty of Science, 2022. urn:nbn:hr:217:170966
Grgurić, Dora
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Grgurić, D. (2022). Priprava ferocenskih estera manoziliranog desmuramil-dipeptida (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:170966

Grgurić, Dora. "Priprava ferocenskih estera manoziliranog desmuramil-dipeptida." Master's thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:170966

Grgurić, Dora. "Priprava ferocenskih estera manoziliranog desmuramil-dipeptida." Master's thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:170966

Grgurić, D. (2022). 'Priprava ferocenskih estera manoziliranog desmuramil-dipeptida', Master's thesis, University of Zagreb, Faculty of Science, accessed 22 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:170966

Grgurić D. Priprava ferocenskih estera manoziliranog desmuramil-dipeptida [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2022 [cited 2024 November 22] Available at: https://urn.nsk.hr/urn:nbn:hr:217:170966

D. Grgurić, "Priprava ferocenskih estera manoziliranog desmuramil-dipeptida", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:217:170966

Metadata
TitlePriprava ferocenskih estera manoziliranog desmuramil-dipeptida
Title (english)Synthesis of ferrocene esters of mannosylated desmuramyl dipeptide
AuthorDora Grgurić
MentorVesna Petrović Peroković (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberŽeljka Soldin (član povjerenstva)
Committee memberSanda Rončević (član povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2022-09-14, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu diplomskog rada opisana je priprava triju ferocenskih estera manoziliranog desmuramil-dipeptida, L-Ala-D-isoGln. Konvergentnim pristupom sintezi najprije su zasebno pripravljena tri fragmenta: manozna podjedinica s razmaknicom od dva atoma ugljika (C2 razmaknica), dipeptid te ferocenski alkoholi, koji su zatim povezani u jednu cjelinu. Benzilima zaštićena manozna podjedinica s C2 razmaknicom pripremljena je u dva sintetska koraka iz 2,3,4,6-tetra-O-benzil-α-D-manopiranoze. Kao polazni dipeptid korišten je komercijalno dostupni zaštićeni desmuramil-dipeptid, Boc-L-Ala-D-isoGln(OBn), kojem je najprije uklonjena benzilna esterska skupina s bočnog ogranka isoGln. Ferocenski alkoholi, pripremljeni na Prehrambeno-biotehnološkom fakultetu Sveučilišta u Zagrebu, sadrže alkilnu poveznicu s različitim brojem metilenskih skupina (n = 2, 4 i 5). Navedeni alkoholi u uvjetima Steglichove esterifikacije vezani su esterskom vezom na karboksilnu skupinu bočnog ogranka izoglutamina. Pripravljenim ferocenskim esterima desmuramil-dipeptida uklonjena je Boczaštitna skupina s amino-skupine alanina te su amidnom vezom vezani na karboksilnu skupinu benzilima zaštićene manozne podjedinice. U posljednjem sintetskom koraku uklonjene su zaštitne skupine s manoze, čime su dobivene ciljne molekule pogodne za ispitivanje in vitro adjuvatnog učinka.
Abstract (english)
In this diploma thesis, preparation of three ferrocene esters of mannosylated desmuramyldipeptide, L-alanyl-D-isoglutamine, is described. Using a convergent approach, fragments, a mannose subunit with a C2 spacer, a dipeptide and ferrocene alcohols were prepared separately, which were subsequently combined into one unit. Commercially available Boc-L-Ala-DisoGln-OBn was used as starting dipeptide. Ferrocene alcohols, that were prepared at the Faculty of Food Techology and Biotechnology, University of Zagreb, contain an alkyl linker with a different number of methylene groups (n = 2, 4 and 5). The alcohols are bound by an ester bond under the conditions of Steglich esterification to the carboxyl group of isoglutamine side chain, which was previously deprotected. The prepared ferrocene esters of desmuramyldipeptide were additionally mannosylated by binding of the -amino group of alanine, which was previously deprotected, to the carboxyl group of the mannose subunit. The benzylprotected mannose subunit with a C2 spacer was prepared in two synthetic steps from 2,3,4,6- tetra-O-benzyl-α-D-mannopyranose. In the last step, protective groups were removed from mannose, which resulted in target molecules suitable for testing the in vitro adjuvant effect.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:170966
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: Research programme
Course: Research programme
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2024-09-14
Terms of useLicence In copyright icon
Created on2022-10-07 09:24:57