Priprava i razdvajanje enantiomera (±)-ektoina

Šišić, Marcela

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master's thesis

Priprava i razdvajanje enantiomera (±)-ektoina

Zagreb: University of Zagreb, Faculty of Science, 2021. urn:nbn:hr:217:929787

Šišić, Marcela

University of Zagreb
Faculty of Science
Department of Chemistry

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APA 6th Edition

Šišić, M. (2021). Priprava i razdvajanje enantiomera (±)-ektoina (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:929787

MLA 8th Edition

Šišić, Marcela. "Priprava i razdvajanje enantiomera (±)-ektoina." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:929787

Chicago 17th Edition

Šišić, Marcela. "Priprava i razdvajanje enantiomera (±)-ektoina." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:929787

Harvard

Šišić, M. (2021). 'Priprava i razdvajanje enantiomera (±)-ektoina', Master's thesis, University of Zagreb, Faculty of Science, accessed 22 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:929787

Vancouver

Šišić M. Priprava i razdvajanje enantiomera (±)-ektoina [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 December 22] Available at: https://urn.nsk.hr/urn:nbn:hr:217:929787

IEEE

M. Šišić, "Priprava i razdvajanje enantiomera (±)-ektoina", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:217:929787

Cite this item: https://urn.nsk.hr/urn:nbn:hr:217:929787

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Metadata

Title	Priprava i razdvajanje enantiomera (±)-ektoina
Title (english)	Synthesis and enantioseparation of (±)-ectoine
Author	Marcela Šišić
Mentor	Marin Roje (mentor)
Committee member	Ines Primožič (predsjednik povjerenstva)
Committee member	Nives Galić (član povjerenstva)
Committee member	Željka Soldin (član povjerenstva)
Committee member	Željka Car (član povjerenstva)
Granter	University of Zagreb Faculty of Science (Department of Chemistry) Zagreb
Defense date and country	2021, Croatia
Scientific / art field, discipline and subdiscipline	NATURAL SCIENCES Chemistry
Abstract	Optimiran je sintetski put priprave (±)-2-metil-1,4,5,6-tetrahidropirimidin-4-karboksilne kiseline, odnosno (±)-ektoina. Sintetski put započinje bromiranjem dihidrofuran-2(3H)-ona. Nastali 3-bromdihidrofuran-2(3H)-on prevodi se u nekoliko reakcijskih koraka u dihidroklorid 2,4-diaminobutanske kiseline. Dobivena 2,4-diaminobutanska kiselina kompleksira se s bakrovim(II) kationom kako bi se u reakciji s 4-nitrofenil-acetatom postigla selektivna acetilacija samo terminalne aminoskupine. Pripravljena 4-acetamido-2-aminobutanska kiselina u zadnjem sintetskom koraku termički se ciklizira u konačni spoj, (±)-ektoin. Odvajanje enantiomera (±)-ektoina provedeno je tekućinskom kromatografijom visoke djelotvornosti i postignuto je primjenom ChiralT kolone uz nekoliko različitih analitičkih metoda. Osim toga, ispitana je prisutnost (+)-ektoina tekućinskom kromatografijom visoke djelotvornosti na Synergi polar – RP koloni u hranjivom mediju u kojem su rasli različiti sojevi bakterija Streptomyces sp. Utvrđena je prisutnost izlučenog (+)-ektoina u hranjivim medijima koji su sadržavali različite koncentracije natrijevog klorida.
Abstract (english)	The synthetic route of preparation of (±)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid or (±)-ectoine was optimized. The synthetic pathway begins with the bromination of dihydrofuran-2-(3H)-one. The resulting 3-bromodihydrofuran-2-(3H)-one is converted in several reaction steps to 2,4-diaminobutanoic acid dihydrochloride. The resulting 2,4- diaminobutanoic acid dihydrochloride is complexed with a copper(II) cation to achieve selective acetylation of only the terminal amino group by reaction with 4-nitrophenyl acetate. The prepared 4-acetamido-2-aminobutanoic acid in the last synthetic step is thermally cyclized to the final compound, (±)-ectoine. Separation of the (±)-ectoine enantiomers is achieved by high-performance liquid chromatography on a ChiralT column using several analytical methods. In addition, the presence of (+)-ectoine was determined by high-performance liquid chromatography on a Synergi polar - RP column in a fermentation broths inoculated with different strains of bacteria Streptomyces sp., and different NaCl concentrations.
Keywords
Keywords (english)
Language	croatian
URN:NBN	urn:nbn:hr:217:929787
Project	Number: N/A Title: Znanstveni centar izvrsnosti za bioprospecting mora Title: Scientific Center of Excellence for Bioprospecting of the sea Acronym: BioProCro Leader: Rozelinda Čož-Rakovac Jurisdiction: Croatia Funder: MZOS Funding stream: ZCI
Study programme	Title: 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 resource	Text
File origin	Born digital
Access conditions	Open access Embargo expiration date: 2022-09-23
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Repository	Repository of the Faculty of Science
Created on	2021-10-20 09:09:44