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dc.contributor.authorMyrvoll, Ragnhild
dc.date.accessioned2014-08-14T08:57:28Z
dc.date.available2014-08-14T08:57:28Z
dc.date.copyright2014
dc.date.issued2014-08-14
dc.identifier.urihttp://hdl.handle.net/11250/217197
dc.description.abstractSynthesis of methyl (6E,8Z,11Z,14Z,17Z)-5-hydroxy-6,8,11,14,17-eicosapentaenate (methyl-5-HEPE) (5), methyl (6E,8Z,11Z,14Z,17Z)-5-oxo-6,8,11,14,17-eicosapentaenate(methyl-5-oxo-EPE) (6) and methyl 4-(3-((2Z,5Z,8Z,11Z)-tetradeca-2,5,8,11-tetraen-1-yl)ocsirane-2-yl)butanate (3) was performed without any significant problems, and with satisfactory yields. We found no good method for the synthesis of methyl (9Z,12Z,15Z,18Z)-5-hydroxyhenicosa-9,12,15,18-tetraenoate (8) and methyl (9Z,12Z,15Z,18Z)-5-oxohenicosa-9,12,15,18-tetraenoate (9), and future work is needed. There was no time to prepare a separation method for the racemic mixture of compound 5 with HPLC. Formation of the chiral ligand (S)-3-etoxy-4-(2-(hydroxydiphenylmethyl)pyrrolidine-1-yl) cyclobut-3-ene-1,2-dione (12) from squaric acid and prolinole was successful and gave satisfactory yields. The use of this ligand in the asymmetric reduction of ketone 6 into respectively 5R or 5S gave ambiguous results and need further exploration. A commercially available model substance for the ketomethyl ester 6 available as methyl-5-oxooctadecanoate (42) was obtained and reduced into methyl-5-hydroksyoktadekanoat (43). Derivatization of compound 43 with Mosher’s acid chloride to make a diastereomeric mixture for use in analysis (HPLC and 1H NMR) were attempted, but gave the product only in enantiomeric form. Studies during the last years have shown that oxygenated PUFAs holds interesting biological activities. The biological activity of compound 5 and 6 will further be characterized pharmacologically at the OXE receptor in a calcium mobilization assay ( Tyagi et al. , 2012) . This test will be indicative of the anti-inflammatory properties of these compounds "in vitro". We had also hoped to carry out this test for compound 5 in its pure enantiomeric form (5R or 5S) and for compound 8 and 9, but since these syntheses were not as successful as we hoped for, this will have to be done as future work.nb_NO
dc.description.sponsorshipNMBU, Pronova BioPharma ASnb_NO
dc.language.isonobnb_NO
dc.publisherNorwegian University of Life Sciences, Ås
dc.subjectOrganic Chemistrynb_NO
dc.subjectFatty Acidsnb_NO
dc.subjectIcosapentaenoic acidnb_NO
dc.subjectEPAnb_NO
dc.subjectAsymmetric reductionnb_NO
dc.subjectSynthesisnb_NO
dc.subjectVDP::Matematikk og Naturvitenskap: 400::Kjemi: 440::Organisk kjemi: 441nb_NO
dc.titleSyntese av noen 5-okso-derivater av (all-Z)-5,8,11,14,17-eicosapentaensyre (EPA) og forsøk på asymmetrisk reduksjon av ketogruppennb_NO
dc.title.alternativeSynthesis of some 5-oxo derivatives of all-Z)-5,8,11,14,17-icosapentaenoic acid (EPA) and attempted asymmetric reduction of the keto groupnb_NO
dc.typeMaster thesisnb_NO
dc.source.pagenumber82nb_NO
dc.relation.projectNMBUnb_NO
dc.description.localcodeM-KJEMInb_NO


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