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Design, synthesis, and characterization of stapled oligosaccharides

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

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Reuber,  Emelie
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Yao,  Ling
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Danglad-Flores,  José Angél       
Hans Riegler, Theorie & Bio-Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Delbianco,  Martina
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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

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Citation

Garcia Ricardo, M., Reuber, E., Yao, L., Danglad-Flores, J. A., Delbianco, M., & Seeberger, P. H. (2022). Design, synthesis, and characterization of stapled oligosaccharides. Journal of the American Chemical Society, 144(40), 18429-18434. doi:10.1021/jacs.2c06882.


Cite as: https://hdl.handle.net/21.11116/0000-000B-32C1-2
Abstract
Stapling short peptides to lock specific conformations and thereby obtain superior pharmacological properties is well established. However, similar concepts have not been applied to oligosaccharides. Here, we describe the design, synthesis, and characterization of the first stapled oligosaccharides. Automated assembly of β-(1,6)-glucans equipped with two alkenyl side chains was followed by on-resin Grubbs metathesis for efficient ring closure with a variety of cross-linkers of different sizes. Oligosaccharide stapling increases enzymatic stability and cell penetration, therefore opening new opportunities for the use of glycans in medicinal chemistry.