Tyrikos-Ergas Theodore, Sletten Eric T, Huang Jhih-Yi, Seeberger Peter H, Delbianco Martina
Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces Am Mühlenberg 1 14476 Potsdam Germany
Department of Chemistry and Biochemistry, Freie Universität Berlin Arnimallee 22 14195 Berlin Germany.
Chem Sci. 2022 Jan 31;13(7):2115-2120. doi: 10.1039/d1sc06063e. eCollection 2022 Feb 16.
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.
硫酸化聚糖参与许多生物过程，这使得结构明确的硫酸化寡糖成为备受追捧的分子探针。这些化合物在合成上颇具挑战，每个寡糖目标都需要特定的合成方案和大量的纯化步骤。在此，我们描述了一种通用的树脂上合成方法，该方法简化了硫酸化聚糖的合成。通过自动聚糖组装（AGA）获得的寡糖主链，经过区域选择性硫酸化和保护基团的水解。该方案与多种单糖兼容，并允许对线性和分支聚糖进行多硫酸化。以良好至优异的总收率制备了七种不同的、具有生物学相关性的硫酸化聚糖。
