On resin synthesis of sulfated oligosaccharides

Tyrikos-Ergas, Theodore; Sletten, Eric T.; Huang, Jhih-Yi; Seeberger, Peter H.; Delbianco, Martina

doi:10.1039/D1SC06063E

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On resin synthesis of sulfated oligosaccharides

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Tyrikos-Ergas, Theodore
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Sletten, Eric T.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Huang, Jhih-Yi
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger, Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare 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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引用

Tyrikos-Ergas, T., Sletten, E. T., Huang, J.-Y., Seeberger, P. H., & Delbianco, M. (2022). On resin synthesis of sulfated oligosaccharides. Chemical Science, 13(7), 2115-2120. doi:10.1039/D1SC06063E.

引用: https://hdl.handle.net/21.11116/0000-0009-FEC3-D

要旨

Sulfated glycans are involved in many biological processes, making well-defined sulfated oligosaccharides highly sought molecular probes. These compounds are a considerable synthetic challenge, with each oligosaccharide target requiring specific synthetic protocols and extensive purifications steps. Here, we describe a general on resin approach that simplifies the synthesis of sulfated glycans. The oligosaccharide backbone, obtained by Automated Glycan Assembly (AGA), is subjected to regioselective sulfation and hydrolysis of protecting groups. The protocol is compatible with several monosaccharides and allows for multi-sulfation of linear and branched glycans. Seven diverse, biologically relevant sulfated glycans were prepared in good to excellent overall yield.