Linker, loading, and reaction scale influence automated glycan assembly

Marlene C S Dal Colle; Manuel G Ricardo; Nives Hribernik; José Danglad-Flores; Peter H Seeberger; Martina Delbianco

doi:10.3762/bjoc.19.77

Linker, loading, and reaction scale influence automated glycan assembly

Beilstein J Org Chem. 2023 Jul 6:19:1015-1020. doi: 10.3762/bjoc.19.77. eCollection 2023.

Authors

Marlene C S Dal Colle^{1

2}, Manuel G Ricardo¹, Nives Hribernik¹, José Danglad-Flores¹, 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

Automated glycan assembly (AGA) affords collections of well-defined glycans in a short amount of time. We systematically analyzed how parameters connected to the solid support affect the AGA outcome for three different glycan sequences. We showed that, while loading and reaction scale did not significantly influence the AGA outcome, the chemical nature of the linker dramatically altered the isolated yields. We identified that the major determinants of AGA yields are cleavage from the solid support and post-AGA purification steps.

Keywords: automated glycan assembly; photocleavable linker; polysaccharides; solid-phase synthesis.

Grants and funding

We thank the Max Planck Society, the German Federal Ministry of Education and Research (BMBF, grant number 13XP5114), and the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation – SFB 1449 – 431232613; sub-project C2) for generous financial support.