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master's thesis
Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija
Zagreb: University of Zagreb, Faculty of Science, 2021. urn:nbn:hr:217:783304
Gojšić, Tomislav
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Gojšić, T. (2021). Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:783304

Gojšić, Tomislav. "Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:783304

Gojšić, Tomislav. "Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:783304

Gojšić, T. (2021). 'Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija', Master's thesis, University of Zagreb, Faculty of Science, accessed 20 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:783304

Gojšić T. Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 November 20] Available at: https://urn.nsk.hr/urn:nbn:hr:217:783304

T. Gojšić, "Adicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:217:783304

Metadata
TitleAdicija triazolnih reagenasa na trostruku vezu derivata propinske kiseline: sinteza i karakterizacija
Title (english)Addition of triazole reagents to triple bonds of propiolic acid derivatives: Synthesis and characterisation
AuthorTomislav Gojšić
MentorSrećko Kirin (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberVladimir Stilinović (član povjerenstva)
Committee memberIvica Đilović (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2021-06-01, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U ovom radu su istraţene adicije triazolnih reagensa 1-hidroksibenzotriazol (HOBt), N,N,N′,N′- tetrametil-O-(1H-benzotriazol-1-il)uronijev heksafluorofosfat (TBTU) i N-[(dimetilamino)-1H-1,2,3- triazolo-[4,5-b]piridin-1-ilmetilen]-N-metilmetanaminijev heksafluorofosfat N-oksid (HATU) na trostruku vezu propinske kiseline i njenog metilnog estera, te sinteza peptidne veze propinske kiseline uz navedene triazolne reagense i uz netriazolni reagens (1-cijano-2-etoksi-2- oksoetilidenaminooksi)dimetilaminomorfolinokarbonijev heksafluorofosfat (COMU). Adicija je proučena na reakciji s metil-propiolatom, dobiven je produkt O- adicije i na propinskoj kiselini u tandemu s sintezom peptidne veze s (1S,2S)-trans-N-Boc-1,2-diaminocikloheksanom, te je dobiven i produkt N- adicije. U reakciji HOBt i metil-propiolata je sintetiziran i pseudo-dimer, nastao od jedne molekule HOBt i dvije molekule metil-propiolata. UtvrĎeno je da je HOBt primarno odgovoran za adiciju. O- adicije su uočene u reakcijama s metil-propiolatom, dok je N- adicija uočena u reakciji s propinskom kiselinom. NMR spektri upućuju na nastanak jednog produkta N- adicije u reakcijama s metil-propiolatom. Korištenjem reagensa COMU-a sintetiziran je ciljni peptid s terminalnom trostrukom vezom.
Abstract (english)
The subject of this thesis is the addition of triazolic reagents 1-hydroxybenzotriazole (HOBt), N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (TBTU) and N- [(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU) to the triple bond of propiolic acid and its methyl ester, and peptide coupling of propiolic acid with either mentioned triazolic reagents or non-triazolic reagent (1- cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU). The addition has been observed in the reaction with methyl-propiolate, where O- addition products have been isolated, and in the reaction with propiolic acid in tandem with peptide coupling with (1S,2S)-trans-N-Boc-1,2-diaminocyclohexane, where N- addition product has been isolated. In the reaction of HOBt and methyl-propiolate a pseudo dimer has been isolated, consisting of one molecule of HOBt and two molecules of methyl-propiolate. HOBt has been observed to be susceptible for the addition. O- additions were observed in reactions with methyl-propiolate, while N- addition was observed in reaction with propiolic acid. NMR spectra indicated that one product in the reactions with methyl-propiolate is a product of N- addition. By using reagent COMU the target peptide has been synthesized.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:783304
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: 2023-06-01
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Created on2021-07-13 11:25:19