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master's thesis
Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida
Zagreb: University of Zagreb, Faculty of Science, 2021. urn:nbn:hr:217:728416
Nuić, Laura
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Nuić, L. (2021). Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:728416

Nuić, Laura. "Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:728416

Nuić, Laura. "Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:728416

Nuić, L. (2021). 'Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida', Master's thesis, University of Zagreb, Faculty of Science, accessed 20 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:728416

Nuić L. Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 November 20] Available at: https://urn.nsk.hr/urn:nbn:hr:217:728416

L. Nuić, "Razvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:217:728416

Metadata
TitleRazvoj sintetskog puta za pripravu lipofilnih derivata desmuramil-dipeptida
Title (english)Development of the synthetic route for the preparation of lipophilic desmuramyl dipeptide derivatives
AuthorLaura Nuić
MentorŽeljka Car (mentor)
Committee memberBiserka Prugovečki (predsjednik povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberVesna Petrović Peroković (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2021-07-15, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu diplomskog rada optimirana je metoda amidacije tert-butiloksikarbonil (Boc) zaštićenog dipeptida ʟ-alanil-ᴅ-izoglutamina lipofilnim aminskim prekursorima. Lipofilne su podjedinice (adamantil-triazolna, adamantilna, dodecilna) uvedene na bočni lanac ᴅ-izoglutamina (ᴅ-isoGln). Adamantilna podjedinica je uvedena na dipeptid preko komercijalno dostupnog 1-aminoadamantan hidroklorida i preko 1,2,3-triazolnog prstena, dobivenog bakrom(I) kataliziranom cikloadicijskom reakcijom iz Boc zaštićenog propargilamina. U toj reakciji je Boc zaštita uvedena in situ te naknadno uklonjena s trifluoroctenom kiselinom. Dodecilamin je pripravljen redukcijom odgovarajućeg azida s LiAlH4. Ispitane su tri metode amidacije. Osim iz kupovnog dipeptida adamantilna ciljna molekula izgrađena je potpuno drugačijim sintetskim pristupom uvođenjem 1-aminoadamantan hidroklorida na bočni ogranak Boc zaštićenog ᴅ-isoGln pomoću dvije najučinkovitije metode amidacije iz prethodnog pristupa. Zatim je uklonjena Boc zaštita te je lipofilni desmuramil-dipeptid dobiven konjugacijom s Boc zaštićenim N-hidroksisukcinimidnim esterom ʟ-alanina. Kao i u koracima prije, Boc zaštita uklonjena je standardnim postupkom.
Abstract (english)
In this Thesis the synthetic route for amidation of tert-butyloxycarbonyl (Boc) protected dipeptide ʟ-alanyl-ᴅ-isoglutamine with lipophilic amine precursors was optimized. Lipophilic subunits (adamantyl triazolyl, adamantyl, dodecyl) were introduced at the ᴅ-isoglutamine (ᴅ-isoGln) side chain. For the incorporation of adamantyl subunit commercially available 1-aminoadamantane hydrochloride was used. The same subunit was also incorporated through 1,2,3-triazole ring obtained via Copper Catalyzed Azide-Alkine Cycloaddition from Boc protected propargylamine. Boc protection was achieved in situ and then removed with trifluoroacetic acid. Dodecylamine was obtained by reduction of corresponding azide derivative with LiAlH4. Three amidation methods were investigated next. Adamantyl desmuramyl dipeptide was also prepared by completely different route starting from the Boc protected ᴅ-isoGln. Two most efficient, previously investigated, amidation methods were used for coupling of ᴅ-isoGln side chain with 1-aminoadamantane hydrochloride in the first step. Boc protection was removed and dipeptide prepared by condensation with Boc protected N-hydroxysuccinimide ester of ʟ-alanine. As in previous steps, Boc group was removed using standard procedure.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:728416
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: 2023-07-15
Terms of useLicence In copyright icon
Created on2021-08-27 11:44:24