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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

Institutional repository: Repository of the Faculty of Science

Cite this document

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

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

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

Šišić, M. (2021). 'Priprava i razdvajanje enantiomera (±)-ektoina', Master's thesis, University of Zagreb, Faculty of Science, accessed 16 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:929787

Šišić M. Priprava i razdvajanje enantiomera (±)-ektoina [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 November 16] Available at: https://urn.nsk.hr/urn:nbn:hr:217:929787

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

Metadata
TitlePriprava i razdvajanje enantiomera (±)-ektoina
Title (english)Synthesis and enantioseparation of (±)-ectoine
AuthorMarcela Šišić
MentorMarin Roje (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberNives Galić (član povjerenstva)
Committee memberŽeljka Soldin (član povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2021, 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)
Languagecroatian
URN:NBNurn:nbn:hr:217:929787
ProjectNumber: 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 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: 2022-09-23
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Created on2021-10-20 09:09:44