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  Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.

Pongener, I., Sletten, E. T., Danglad-Flores, J. A., Seeberger, P. H., & Miller, G. J. (2024). Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly. Organic & Biomolecular Chemistry, 22(7), 1395-1399. doi:10.1039/d3ob01909h.

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Pongener, Imlirenla, Author
Sletten, Eric T.1, Author           
Danglad-Flores, José Angél1, Author                 
Seeberger, Peter H.1, Author                 
Miller, Gavin J, Author
Affiliations:
1Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 Abstract: Herein we utilise automated glycan assembly to complete solid-phase synthesis of defined heparan sulfate oligosaccharides, employing challenging D-glucuronate disaccharide donors. Using an orthogonally protected D-GlcN-alpha-D-GlcA donor, milligram-scale synthesis of a heparan sulfate tetrasaccharide is completed in 18% yield over five steps. Furthermore, orthogonal protecting groups enabled regiospecific on-resin 6-O-sulfation. This methodology provides an important benchmark for the rapid assembly of biologically relevant heparan sulfate sequences.

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Language(s): eng - English
 Dates: 2024-01-242024
 Publication Status: Issued
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1039/d3ob01909h
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Title: Organic & Biomolecular Chemistry
  Other : Organic and Biomolecular Chemistry
  Abbreviation : Org. Biomol. Chem.
Source Genre: Journal
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Publ. Info: Cambridge : Royal Society of Chemistry
Pages: - Volume / Issue: 22 (7) Sequence Number: - Start / End Page: 1395 - 1399 Identifier: ISSN: 1477-0520