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doctoral thesis
Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama
Zagreb: University of Zagreb, Faculty of Science, 2015. urn:nbn:hr:217:927553
Šporec, Anita
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Šporec, A. (2015). Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:927553

Šporec, Anita. "Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama." Doctoral thesis, University of Zagreb, Faculty of Science, 2015. https://urn.nsk.hr/urn:nbn:hr:217:927553

Šporec, Anita. "Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama." Doctoral thesis, University of Zagreb, Faculty of Science, 2015. https://urn.nsk.hr/urn:nbn:hr:217:927553

Šporec, A. (2015). 'Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:927553

Šporec A. Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2015 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:217:927553

A. Šporec, "Enantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2015. Available at: https://urn.nsk.hr/urn:nbn:hr:217:927553

Metadata
TitleEnantioselektivna kromatografija β-aminoalkohola na polisaharidnim kiralnim nepokretnim fazama
Title (english)Enantioselective chromatography of β-aminoalcohols on polysaccharide based chiral stationary phases
AuthorAnita Šporec
MBZ: 251756
MentorVladimir Vinković (mentor)
MBZ: 71214
Committee memberVlasta Drevenkar (predsjednik povjerenstva)
Committee memberVladimir Vinković (član povjerenstva)
MBZ: 71214
Committee memberSrđanka Tomić-Pisarović (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2015-07-13, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
Pripravljeno je dvadeset i pet modelnih β-aminoalkohola (β-aa) podijeljenih u tri skupine sobzirom na način sinteze. Prva skupina spojeva sintetizirana je katalitičkom amonolizom racemičnih derivata stiren-oksida (43a-50a), druga skupina amonolizom glicidil-fenil-etera (57-65), a treća amonolizom simetričnih meso-epoksida (71-78). Sintetizirani spojevi suracemične smjese R- i S-enantiomera. Razvijene su enantioselektivne tekućinsko kromatografske metode za njihovo odjeljivanje na četiri „kiralne kolone“, uz detekciju spojeva UV-detektorom s nizom fotodioda. Za svaku kombinaciju sastava pokretne faze i polisaharidne kiralne nepokretne faze razmatrani su enantio-kromatografski pokazatelji (k1, α, Rs). Za potvrdu redoslijeda ispiranja enantiomera (R- ili S-) s kolone, pripravljeni su enantiomerno čisti predstavnici triju skupina β-aa. Na temelju rezultata enantioselektivne analize predloženi su mogući mehanizmi kiralnog prepoznavanja modelnih β-aa. Primjenjivost razvijenih metoda potvrđena je odjeljivanjem enantiomera četiriju kardiovaskularnih lijekova čija je djelatna tvar po sastavu β-aa: atenolola, sotalola, bisoprolola i karvedilola. Kolona Chiralcel OD pokazala se učinkovitom za odvajanje enantiomera kako modelnih β-aa tako i kardiovaskularnih lijekova.
Abstract (english)
Synthesis of twenty five model β-amino alcohols (β-aa) is described. Based on the synthetic approach applied for preparation, three classes of β-aa are identified: the first class is made by catalytic amonolysis of racemic derivatives of styrene oxide (43a-50a), the second by amonolysis of ethyl glycidyl ether (57-65) and the third by amonolysis of symmetric mesoepoxides(71-78). Prepared compounds were racemic mixtures of R- and S- enantiomers and efficient analytical methods for enantioseparation were developed using “chiral columns” connected with high performance liquid chromatograph and UV diode-array detector. For each combination of mobile phase composition and polysaccharide-based stationary phase, enantio-chromatographic parameters were studied (k1, Rs, α). For confirmation of enantiomerelution order (R- or S-) from the column, enantioenriched representative compounds were synthetized. Based on the enantioselective chromatography results mechanisms of chiral recognition of β-aa were proposed. Applicability of developed enantioselective methods was confirmed on four cardiovascular drugs with β-aa moiety: atenolol, sotalol, bisoprolol, carvedilol. It was found that the best enantioseparation of model β-amino alcohols and tested cardiovascular drugs was obtained with Chiralcel OD column.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:927553
Study programmeTitle: Doctoral study in chemistry
Study programme type: university
Study level: postgraduate
Academic / professional title: doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija (doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija)
Type of resourceText
Extent205 str. ; 30 cm
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2017-03-02 15:28:14