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  Design, synthesis, and characterization of stapled oligosaccharides

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.

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 Creators:
Garcia Ricardo, Manuel1, Author                 
Reuber, Emelie2, Author           
Yao, Ling2, Author           
Danglad-Flores, José Angél3, Author                 
Delbianco, Martina4, Author           
Seeberger, Peter H.2, Author                 
Affiliations:
1Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              
2Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              
3Hans Riegler, Theorie & Bio-Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863502              
4Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2559692              

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 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.

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Language(s): eng - English
 Dates: 2022-09-292022
 Publication Status: Published in print
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 Identifiers: DOI: 10.1021/jacs.2c06882
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 144 (40) Sequence Number: - Start / End Page: 18429 - 18434 Identifier: ISSN: 0002-7863