Phosphates as Assisting Groups in Glycan Synthesis

Eric T Sletten; Giulio Fittolani; Nives Hribernik; Marlene C S Dal Colle; Peter H Seeberger; Martina Delbianco

doi:10.1021/acscentsci.3c00896

Phosphates as Assisting Groups in Glycan Synthesis

ACS Cent Sci. 2023 Dec 20;10(1):138-142. doi: 10.1021/acscentsci.3c00896. eCollection 2024 Jan 24.

Authors

Eric T Sletten¹, Giulio Fittolani¹, Nives Hribernik¹, Marlene C S Dal Colle^{1

2}, Peter H Seeberger^{1

2}, Martina Delbianco¹

Affiliations

¹ Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
² Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.

Abstract

In nature, phosphates are added to and cleaved from molecules to direct biological pathways. The concept was adapted to overcome limitations in the chemical synthesis of complex oligosaccharides. Phosphates were chemically placed on synthetic glycans to ensure site-specific enzymatic elongation by sialylation. In addition, the deliberate placement of phosphates helped to solubilize and isolate aggregating glycans. Upon traceless removal of the phosphates by enzymatic treatment with alkaline phosphatase, the native glycan structure was revealed, and the assembly of glycan nanostructures was triggered.