Synthesis 2023; 55(09): 1337-1354
DOI: 10.1055/a-1938-2293
special topic
Bürgenstock Special Section 2022 – Future Stars in Organic Chemistry

Recent Developments in Solid-Phase Glycan Synthesis

a   Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
b   Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany
,
a   Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany
› Author Affiliations
This work was supported by the Bundesministerium für Bildung und Forschung (German Federal Ministry of Education and Research) (Grant no. 13XP5114), the Max-Planck-Gesellschaft (Max Plank Society­), and the MPG-FhG Cooperation Project GLyco3Dsplay. J.Y.H acknowledges the International Max Planck Research School on Multiscale­ Bio-Systems for funding.


Abstract

Solid-phase glycan synthesis (SPGS) is a valuable approach to access broad collections of complex, well-defined oligo- and polysaccharides in short amounts of time. The target structure is assembled following iterative cycles of glycosylation and deprotection, often aided by automated machines. To expand the scope of SPGS, new solid supports, linkers, glycosylation and deprotection reactions, and functionalization strategies are constantly being developed. Here we discuss the state of the art of SPGS, with particular focus on the chemistry happening on solid-phase. We highlight recent achievements as well as challenges to be addressed to expand the scope of SPGS even further.

1 Introduction

2 Solid-Phase Glycan Synthesis

2.1 The Solid Support

2.2 The Linker

2.3 The Assembly Process

2.4 Post-Assembly Manipulations

2.5 The Analysis

2.6 Cleavage from the Solid Support

3 Conclusion and Outlook



Publication History

Received: 14 July 2022

Accepted after revision: 07 September 2022

Accepted Manuscript online:
07 September 2022

Article published online:
18 October 2022

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