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Synthetic approach towards a panel of 13C5-labeled glycosphingolipids for glycosphongolipid storage disorders

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Synthetic approach towards a panel of 13C5-labeled glycosphingolipids for glycosphongolipid storage disorders

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Samenvatting

The aim of this project was to develop a synthetic approach towards a panel of 13C5-labeled glycosphingolipids for glycosphingolipid storage disorders. The first step was to synthesize the sphingosine backbone with the emphasis on introducing the labeled fatty tail in the final step. The sphingosine backbone has been successfully synthesized from Fmoc-L-Serine. During the first step, Fmoc-L-Serine was converted to the corresponding Weinreb amide. After protecting the 1⁰ alcohol, the Weinreb amide was converted into a α-β ketone. This ketone was then selectively reduced to the anti-alcohol and afterward protected. After deprotection of the 1⁰ alcohol, the fatty chain was installed using cross metathesis. Previously, in work done by P. van Oerle, this happened after reducing the ketone. This new route allows for the installment of a fatty chain with 13C5-atoms in the final phase, which is much more cost efficient.
The second step was the synthesis of four different sugar donors who would be coupled to the sphingosine backbone in a later stage. The four sugar donors of interest were galactose, glucose, lactose and 3-O-sulfogalactose. Galactose imidate and glucose imidate have successfully been synthesized and coupled to the sphingosine backbone. Deprotection of the protected galactosylsphingosine and glucosylsphingosine have been achieved as well and has been confirmed by LC-MS analysis. Preliminary NMR data suggests that lactose imidate has successfully been coupled to the sphingosine backbone. However, deprotection and more analysis are still necessary to fully identify this compound. The synthesis of the 3-O-sulfogalactose donor has not been finished yet by a lack of time and resources. At the moment, the synthesis is in its final stage and could be finished if more time was available.

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OrganisatieAvans Hogeschool
OpleidingChemie-Breda
AfdelingATGM Academie voor de technologie van Gezondheid en Milieu
PartnersUniversity of Leiden
Jaar2016
TypeBachelor
TaalEngels

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