Thermodynamic and structural behaviour of α-Galactosylceramide and 
C6-functionalized α-GalCer in 2D layers at the air-liquid interface

Brezesinski, Gerald; Calow, Adam D. J.; Pereira, Claney Lebev; Seeberger, Peter H.

doi:10.1002/cbic.201900491

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Thermodynamic and structural behaviour of α-Galactosylceramide and C6-functionalized α-GalCer in 2D layers at the air-liquid interface

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Brezesinski, Gerald
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Calow, Adam D. J.
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pereira, Claney Lebev
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger, Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Brezesinski, G., Calow, A. D. J., Pereira, C. L., & Seeberger, P. H. (2020). Thermodynamic and structural behaviour of α-Galactosylceramide and C6-functionalized α-GalCer in 2D layers at the air-liquid interface. ChemBioChem: A European Journal of Chemical Biology, 21(1-2), 241-247. doi:10.1002/cbic.201900491.

Cite as: https://hdl.handle.net/21.11116/0000-0004-C7AD-9

Abstract

α-Galactosylceramide (KRN7000) is a ligand for the glycoprotein CD1d that presents lipid antigens to natural killer T cells. Therefore, KRN7000 as well as some modified version thereof have been widely investigated as part of novel immunotherapies. To examine the impact of structural modification, we investigated KRN7000 and C6-modified KRN7000 at the air-liquid interface using monolayer isotherms, BAM, IRRAS, GIXD and TRXF. The amino group has no influence on the highly ordered sub-gel structures found at lateral pressures relevant for biological membranes. Neither lateral compression nor the protonation state of the amino group has a measurable effect on the lattice structure, which is defined by strong and rigid intermolecular hydrogen-bonds. However, the first-order phase transition found for the C6-functionalized α-GalCer is connected with an extraordinary surface inhibited nucleation. Our study demonstrates that KRN7000 can be functionalized at C6 without significantly changing the structural properties.