Design, Synthesis, and Characterization of Stapled Oligosaccharides

[Image: see text] 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...

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Autores principales: Ricardo, Manuel G., Reuber, Emelie E., Yao, Ling, Danglad-Flores, José, Delbianco, Martina, Seeberger, Peter H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9562281/
https://www.ncbi.nlm.nih.gov/pubmed/36173281
http://dx.doi.org/10.1021/jacs.2c06882
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author Ricardo, Manuel G.
Reuber, Emelie E.
Yao, Ling
Danglad-Flores, José
Delbianco, Martina
Seeberger, Peter H.
author_facet Ricardo, Manuel G.
Reuber, Emelie E.
Yao, Ling
Danglad-Flores, José
Delbianco, Martina
Seeberger, Peter H.
author_sort Ricardo, Manuel G.
collection PubMed
description [Image: see text] 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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spelling pubmed-95622812022-10-15 Design, Synthesis, and Characterization of Stapled Oligosaccharides Ricardo, Manuel G. Reuber, Emelie E. Yao, Ling Danglad-Flores, José Delbianco, Martina Seeberger, Peter H. J Am Chem Soc [Image: see text] 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. American Chemical Society 2022-09-29 2022-10-12 /pmc/articles/PMC9562281/ /pubmed/36173281 http://dx.doi.org/10.1021/jacs.2c06882 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ricardo, Manuel G.
Reuber, Emelie E.
Yao, Ling
Danglad-Flores, José
Delbianco, Martina
Seeberger, Peter H.
Design, Synthesis, and Characterization of Stapled Oligosaccharides
title Design, Synthesis, and Characterization of Stapled Oligosaccharides
title_full Design, Synthesis, and Characterization of Stapled Oligosaccharides
title_fullStr Design, Synthesis, and Characterization of Stapled Oligosaccharides
title_full_unstemmed Design, Synthesis, and Characterization of Stapled Oligosaccharides
title_short Design, Synthesis, and Characterization of Stapled Oligosaccharides
title_sort design, synthesis, and characterization of stapled oligosaccharides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9562281/
https://www.ncbi.nlm.nih.gov/pubmed/36173281
http://dx.doi.org/10.1021/jacs.2c06882
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