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  Automated assembly of starch and glycogen polysaccharides

Zhu, Y., Delbianco, M., & Seeberger, P. H. (2021). Automated assembly of starch and glycogen polysaccharides. Journal of the American Chemical Society, 143(26), 9758-9768. doi:10.1021/jacs.1c02188.

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 Creators:
Zhu, Yuntao1, Author              
Delbianco, Martina2, Author              
Seeberger, Peter H.1, Author              
Affiliations:
1Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              
2Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2559692              

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Free keywords: Carbohydrates; Protective groups; Organic compounds; Chemical biology; Post-translational modification
 Abstract: Polysaccharides are Nature’s most abundant biomaterials essential for plant cell wall construction and energy storage. Seemingly minor structural differences result in entirely different functions: cellulose, a β (1–4) linked glucose polymer, forms fibrils that can support large trees, while amylose, an α (1–4) linked glucose polymer forms soft hollow fibers used for energy storage. A detailed understanding of polysaccharide structures requires pure materials that cannot be isolated from natural sources. Automated Glycan Assembly provides quick access to trans-linked glycans analogues of cellulose, but the stereoselective installation of multiple cis-glycosidic linkages present in amylose has not been possible to date. Here, we identify thioglycoside building blocks with different protecting group patterns that, in concert with temperature and solvent control, achieve excellent stereoselectivity during the synthesis of linear and branched α-glucan polymers with up to 20 cis-glycosidic linkages. The molecules prepared with the new method will serve as probes to understand the biosynthesis and the structure of α-glucans.

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Language(s): eng - English
 Dates: 2021-06-112021
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1021/jacs.1c02188
BibTex Citekey: doi:10.1021/jacs.1c02188
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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: 143 (26) Sequence Number: - Start / End Page: 9758 - 9768 Identifier: ISSN: 0002-7863