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master's thesis
Kinetička rezolucija fluoriranih alkohola katalizirana lipazama
Zagreb: University of Zagreb, Faculty of Science, 2019. urn:nbn:hr:217:807825
Ević, Valentina
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Ević, V. (2019). Kinetička rezolucija fluoriranih alkohola katalizirana lipazama (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:807825

Ević, Valentina. "Kinetička rezolucija fluoriranih alkohola katalizirana lipazama." Master's thesis, University of Zagreb, Faculty of Science, 2019. https://urn.nsk.hr/urn:nbn:hr:217:807825

Ević, Valentina. "Kinetička rezolucija fluoriranih alkohola katalizirana lipazama." Master's thesis, University of Zagreb, Faculty of Science, 2019. https://urn.nsk.hr/urn:nbn:hr:217:807825

Ević, V. (2019). 'Kinetička rezolucija fluoriranih alkohola katalizirana lipazama', Master's thesis, University of Zagreb, Faculty of Science, accessed 25 May 2024, https://urn.nsk.hr/urn:nbn:hr:217:807825

Ević V. Kinetička rezolucija fluoriranih alkohola katalizirana lipazama [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2019 [cited 2024 May 25] Available at: https://urn.nsk.hr/urn:nbn:hr:217:807825

V. Ević, "Kinetička rezolucija fluoriranih alkohola katalizirana lipazama", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2019. Available at: https://urn.nsk.hr/urn:nbn:hr:217:807825

Metadata
TitleKinetička rezolucija fluoriranih alkohola katalizirana lipazama
Title (english)Kinetic resolution of fluoroalcohols catalysed by lipases
AuthorValentina Ević
MentorMaja Majeric Elenkov (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberJasmina Rokov Plavec (član povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberIvana Biljan (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2019-02-21, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Optički čisti spojevi su vrijedni prekursori u farmaceutskoj industriji. Fluorirani spojevi su aktivne tvari u mnogim lijekovima, stoga su nove mogućnosti sinteze fluoriranih kiralnih graĎevnih blokova posebno zanimljive i vrijedne. U ovom radu sintetizirana su tri racemična derivata 1-fluorpropan-2-ola koji su supstituirani u položaju 3 azido (1a), cijano (2a) skupinom i klorom (3a) te su korišteni kao supstrati za kinetičku rezoluciju kataliziranu lipazama. Pripravljeni su i odgovarajući racemični acetati alkohola (1b-3b) kao standardi. U ovim reakcijama ispitano je pet različitih lipaza. Najaktivnije i najselektivnije lipaze za pojedini alkohol testirane su u različitim organskim otapalima. Lipaze su pokazale nisku do srednje visoku enantioselektivnost prema ispitanim supstratima (E = 1 – 44). U preparativnim reakcijama kataliziranim lipazama najviše enantioselektivnosti, pripravljeni su enantiomerno obogaćeni produkti: (R)-1a (ev = 65 – 85 %), (S)-1b (ev = 92 %), (R)-2a (ev = 84 %), (S)-2b (ev = 68 %) te smjesa (S)-3a (ev = 30 %) i (R)-3b (ev = 69 %).
Abstract (english)
Optically pure compunds are valuable precursors in pharmaceutical industry. Active ingridients in many drugs are fluorinated compounds, therefore the new possibilities in synthesis of fluorinated chiral building blocks are especially interesting and valuable. In this thesis three racemic derivatives of 1-fluoropropan-2-ol were synthesized, substituated at position 3 with azide (1a), cyanide (2a) and chloride (3a) and used as substrates in lipasecatalyzed kinetic resolution. Corresponding racemic acetates were prepared (1b-3b) as standards. Five different lipases were tested. Lipase with highest activity and selectivity with each alcohol was tested in different organic solvents. Lipases have shown low to high enantioselectivity toward supstrates (E = 1 – 44). In preparative-scale reactions catalysed by lipases with highest enantioselectivity, enantiomerically enriched products were prepared: (R)-1a (ee = 65 – 85 %), (S)-1b (ee = 92 %), (R)-2a (ee = 84 %), (S)-2b (ee = 68 %), and mixture of (S)-3a (ee = 30 %) and (R)-3b (ee = 69 %).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:807825
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
Terms of useLicence In copyright icon
Created on2019-03-07 11:01:53