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  Synthesis of Gb(3) glycosphingolipids with labeled head groups: Distribution in phase-separated giant unilamellar vesicles

Sibold, J., Kettelhoit, K., Vuong, L., Liu, F., Werz, D. B., & Steinem, C. (2019). Synthesis of Gb(3) 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.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-182C-0 Version Permalink: http://hdl.handle.net/21.11116/0000-0005-4A2D-7
Genre: Journal Article

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 Creators:
Sibold, J., Author
Kettelhoit, K., Author
Vuong, L., Author
Liu, F., Author
Werz, D. B., Author
Steinem, Claudia1, Author              
Affiliations:
1Max Planck Fellow Group Membrane-based biomimetic nano- and micro-compartments, Max Planck Institute for Dynamics and Self-Organization, Max Planck Society, ou_2586691              

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Free keywords: carbohydrates; fatty acids; fluorescence; membranes; toxins
 Abstract: The receptor lipid Gb(3) is responsible for the specific internalization of Shiga toxin (STx) into cells. The head group of Gb(3) 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 Gb(3) glycosphingolipids labeled with a BODIPY fluorophore attached to the head group was synthesized. C-24 fatty acids, saturated, unsaturated, alpha-hydroxylated derivatives, and a combination thereof, were attached to the sphingosine backbone. The synthetic Gb(3) glycosphingolipids were reconstituted into coexisting liquid-ordered (l(o))/liquid-disordered (l(d)) giant unilamellar vesicles (GUVs), and STx binding was verified by fluorescence microscopy. Gb(3) with the C-24:0 fatty acid partitioned mostly in the l(o) phase, while the unsaturated C-24:1 fatty acid distributes more into the l(d) phase. The alpha-hydroxylation does not influence its partitioning.

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Language(s): eng - English
 Dates: 2019-09-172019-12-02
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1002/anie.201910148
 Degree: -

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Title: Angewandte Chemie International Edition
Source Genre: Journal
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Publ. Info: -
Pages: - Volume / Issue: 58 (49) Sequence Number: - Start / End Page: 17805 - 17813 Identifier: -