Synthesis of Gb3 glycosphingolipids with labeled head groups: Distribution in 
phase-separated giant unilamellar vesicles

Sibold, J.; Kettelhoit, K.; Vuong, L.; Liu, F.; Werz, D. B.; Steinem, Claudia

doi:10.1002/anie.201910148

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Synthesis of Gb₃ glycosphingolipids with labeled head groups: Distribution in phase-separated giant unilamellar vesicles

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Steinem, Claudia
Max Planck Fellow Group Membrane-based biomimetic nano- and micro-compartments, Max Planck Institute for Dynamics and Self-Organization, Max Planck Society;

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Citation

Sibold, J., Kettelhoit, K., Vuong, L., Liu, F., Werz, D. B., & Steinem, C. (2019). Synthesis of Gb₃ glycosphingolipids with labeled head groups: Distribution in phase-separated giant unilamellar vesicles. Angewandte Chemie International Edition, 58(49), 17805-17813. doi:10.1002/anie.201910148.

Cite as: https://hdl.handle.net/21.11116/0000-0005-4887-2

Abstract

The receptor lipid Gb3 is responsible for the specific internalization of Shiga toxin (STx) into cells. The head group of Gb3 defines the specificity of STx binding, and the backbone with different fatty acids is expected to influence its localization within membranes impacting membrane organization and protein internalization. To investigate this influence, a set of Gb3 glycosphingolipids labeled with a BODIPY fluorophore attached to the head group was synthesized. C24 fatty acids, saturated, unsaturated, α-hydroxylated derivatives, and a combination thereof, were attached to the sphingosine backbone. The synthetic Gb3 glycosphingolipids were reconstituted into coexisting liquid-ordered (lo )/liquid-disordered (ld ) giant unilamellar vesicles (GUVs), and STx binding was verified by fluorescence microscopy. Gb3 with the C24:0 fatty acid partitioned mostly in the lo phase, while the unsaturated C24:1 fatty acid distributes more into the ld phase. The α-hydroxylation does not influence its partitioning.