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Universiteit Gent - Laboratorium voor Organische en Bio-organische Synthese

Contact details
Traineeship proposition
Stageonderwerp 2008-2009: Vaste-fasesynthese van heterocyclische verbindingen met potentiële biologische activiteit
De studente zal de volgende technieken leren gebruiken:
- werken met droge solventen onder inerte atmosfeer
- synthese in oplossing
- synthese aan een hars
- dunnelaagchromatografie
- uitvoering en interpretatie van kleurtesten aan een hars
- chromatografische scheidingstechnieken (open kolomchromatografie, preparatieve HPLC)
- interpretatie van LC-MS-analyses
- interpretatie van 1H- en 13C-NMR-spectra
- opname en interpretatie van IR-spectra
- interpretatie van massaspectra
De studente zal ook kennismaken met moderne technieken voor literatuuronderzoek (electronische databanken zoals Web of Science en SciFinder), en met de wetenschappelijke literatuur.
Abstract Bachelor Project FBT 2018-2019: Towards an efficient synthesis of peloruside analogues
Cancer has a big impact on society, being a prevalent cause of death and disability throughout the world. Although there are already treatment options available for some types of cancer a panacea does not yet exist. Through diligent research we can however discover new treatments, improve the effectiveness of current ones and lower the cost of these medications. Paclitaxel (also known as Taxol®) is a well-known chemotherapeutic agent, often used in clinical settings. It exerts its function by binding to microtubules in the cytoplasm and inhibiting their depolymerization, thereby impeding microtubular functions during the cell division, making it the prime example of the microtubule targeting agents.
Nevertheless the clinical importance of paclitaxel and other taxanes, their efficiency and efficacy is limited by the development of multidrug resistance, a disadvantaged pharmacokinetic profile and toxicity. Combined with a need for novel, improved agents, these shortcomings stimulate research into new microtubule-stabilizing agents.
(+)-Peloruside A and B, two polyketides isolated from the marine sponge Mycale hentscheli, show a cytotoxic activity similar to that of paclitaxel. As a result of improved pharmacokinetics, activity towards resistant tumours and better tolerability, this compound class has garnered a strong interest as a potential second generation of MSAs.
Following their discovery, (+)-peloruside A and analogues have been synthesized via long and elaborate routes. Coupled with their low natural abundance, their chemical complexity hinders their economic viability. Furthermore, all synthesized analogues so far have shown a greatly decreased activity. The Laboratory for Organic and Bio-Organic Synthesis researches improved synthetic routes towards pelorusanes as well as simplified analogues. This bachelor thesis aims to make a contribution towards the development of a synthesis for a peloruside analogue building block via a new synthetic route.
This building block was synthesized in eight steps starting from commercially available starting materials. The use of a organozinc reagent for introducing the allylic alcohol functionality is the key improvement. This approach resulted in an improved synthesis with a total yield of 13% in seven steps.
Samenvatting eindwerk 2011-2012:
Synthese van nieuwe amino- en azidocyclitolen uitgaande van D-(-)-kinazuur
Wegens confidentialiteit kan de samenvatting niet gepubliceerd worden.
Samenvatting eindwerk 2008-2009: Bijdrage tot de vaste-fasesynthese van benzodiazepineanalogen
Wegens confidentialiteit kan de samenvatting niet gepubliceerd worden.


Krijgslaan 281
9000 Gent


Traineeship supervisor
Johan Van der Eycken
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