Citation for published version (APA): Fodran, P. (2015). Stereoselective synthesis of glycerol-based lipids [S.l.]: [S.n.]

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1 University of Groningen Stereoselective synthesis of glycerol-based lipids Fodran, Peter IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2015 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Fodran, P. (2015). Stereoselective synthesis of glycerol-based lipids [S.l.]: [S.n.] Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date:

2 Samenvatting Het idee dat verzeepbare fosfolipiden alleen functioneren als bouwstenen en energiebron voor de cel werd weerlegd door de ontdekking van signaalfuncties van fosfolipiden. Tegenwoordig worden deze lipiden uitgebreid bestudeerd, en steeds worden nieuwe functies ontdekt. Een aspect wat de studie van fosfolipiden bemoeilijkt, is hun gelimiteerde beschikbaarheid in zuivere vorm. Biologische membranen, de hoofdbron van fosfolipiden, bestaan vaak uit honderden zeer vergelijkbare lipiden. Daarin is soms maar een zeer geringe hoeveelheid van een bepaald lipide met een specifieke fysiologische eigenschap aanwezig. Het vinden en isoleren van dit lipide doet denken aan het spreekwoord een speld in een hooiberg zoeken. Hoewel de organische chemie niet direct kan helpen naar de zoektocht naar de speld, geeft het wel een andere oplossing; het maken van een zo n speld. Dit vereist wel een efficiënte strategie voor de synthese van gedefinieerde, chemisch zuivere lipiden en hun derivaten. Dat is wat dit proefschrift beschrijft. Hoofdstuk 2 beschrijft de modulaire synthese van vertakte vetzuren, vaak hoofdbestanddelen van membranen van bacteriële pathogenen. De beschreven route maakt het mogelijk om vetzuren te synthetiseren die methylsubstituenten hebben op elke positie van de lineaire keten, in combinatie met de gewenste absolute configuratie. Figure 1. De modulaire synthese van vertakte vetzuren Deze modulaire benadering is succesvol toegepast in de synthese van 3 verschillende vetzuren in hoeveelheden die toereikend zijn voor verdere studies. 175

3 Ondanks het feit dat glycerofosfolipiden een vrij eenvoudige structuur lijken te hebben, is hun synthese verrassend complex. Hoofdstuk 3 is dan ook gewijd aan de synthese van deze glycerofosfolipiden. Met behulp van een kobalt katalysator kan een beschermd glycidol regioselectief worden geopend. Het verkregen monoacylglycerol wordt nogmaals veresterd in dezelfde reactiekolf. Het resulterende beschermde diacylglycerol wordt ontschermd zonder acylmigratie en vervolgens omgezet naar het fosfolipide. Figure 2. Eénpotssynthese van beschermde diacylglycerolen en de omzetting naar een fosfolipide Hoofdstuk 4 is een uitbreiding van deze methodologie tot de synthese van triacylglycerolen. Door glycidyl-esters te gebruiken als startmateriaal, kunnen onder dezelfde condities enantiozuivere triacylglycerolen worden geïsoleerd. Deze methodologie is gedemonstreerd in de synthese van 18 verschillende triacylglycerolen. Figure 3. Een efficiënte, 3-stapssynthese van triacylglycerolen. 176

4 Bovendien beschrijft dit hoofdstuk ook de eerste stap in de richting van de geautomatiseerde synthese van triacylglycerolen met behulp van een pipetteer robot. De verkregen triacylglycerolen kunnen gebruikt worden als standaarden in de analyse van triacylglycerolmengsels zoals in melkvet. Hoofdstuk 2 en 3 beschrijven een strategie voor de synthese van fosfolipiden met methylvertakte vetzuren. Deze lipiden zijn gesynthetiseerd in hoeveelheden die initiële studies toelieten naar hun eigenschappen als membraanlipiden. Figure 4. De invloed van methylvertakkingen op de organisatie van de lipide bilaag, links de moleculaire dynamicasimulaties. De fosfolipiden werden gebruikt in liposomen. De bilaag van deze liposomen is gesimuleerd met moleculaire dynamica. Het blijkt dat kanaalvormende membraaneiwitten succesvol in deze liposomen kunnen worden gereconstitueerd. Hoofdstuk 6 is ook gewijd aan de invloed van lipiden op de functie van eiwitten, maar dan vanuit een ander perspectief. Eiwitlipidering is een posttranslationele modificatie waarbij lipiden de activiteit van eiwitten sturen. Dit hoofdstuk beschrijft 177

5 de synthese van een lipide-sonde, die gebruikt zou kunnen worden in levende cellen voor de modificatie van eiwitten met lipiden om ze dusdanig te kunnen bestuderen. Figure 5. Een sonde voor de studie van eiwitlipidering laat een schone en snelle dipolaire cycloadditie zien. Hoofstuk 7 is gewijd aan (fosfo)lipiden die gevonden worden in Archaea. Archaea vormen één van de domeinen van het leven, die in een beginstadium van de evolutie is afgesplitst van de andere twee domeinen. Figure 6. ( I ) Synthese van een intermediair uit de biosynthese van archaiële lipiden in verband met de identificatie van het betrokken enzym. ( II ) Epoxide ringopening als de belangrijkste stap in de totaalsynthese van cycloarchaeol. 178

6 De gescheiden evolutie van deze domeinen liet toe dat Archaea hun eigen route hebben ontwikkeld voor lipidensynthese. Het bestuderen van deze syntheseroute is uitdagend, omdat er maar enkele analyses bestaan en de bijhorende biosynthese-intermediairen niet beschikbaar zijn. Hoofdstuk 7 beschrijft de synthese van één van deze intermediairen, die leidde tot de identificatie van een enzym in de lipide-biosynthese. Hoofdstuk 7 beschrijft ook een belangrijke stap in de totaalsynthese van cycloachaeol, een membraanlipide uit Archaea. 179

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