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Book Chapter

Automated oligosaccharide synthesis : the past, present, and future


Downey,  Michael
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;


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

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Downey, M., & Seeberger, P. H. (2021). Automated oligosaccharide synthesis: the past, present, and future. In Comprehensive glycoscience Vol. 2 "Analysis and preparation of glycans" (pp. 561-601). Amsterdam: Elsevier B.V. doi:10.1016/B978-0-12-819475-1.00106-1.

Cite as: https://hdl.handle.net/21.11116/0000-0008-AE5B-F
Of the three most important classes of biomolecules: oligopeptides (proteins), oligonucleotides, and oligosaccharides, the last remains the most difficult to synthesize in an automated fashion due to the presence of many stereocenters and bond connections possible among a large pool of monosaccharide monomers. For these reasons, it was not until the early 21st century, nearly 50years after automated oligopeptide synthesis was first available, that a preliminary method presented to automate the synthesis of carbohydrates.1.The Past: We will discuss a brief history of automated biomolecule assembly methods available that served as inspiration for automated glycan assembly (AGA) as well as early solid-phase oligosaccharide synthesis, leading up to automation of the processes. We will also discuss a progression in the glycans available up to 2001.2.The Present: Leading up to where we are right now (2001 to today) and some key syntheses and applications especially from the last years. We will compare automated glycan assembly, programmable one-pot synthesis, chemo-enzymatic synthesis, as well as fluorous- and HPLC-assisted methods aiming at partial automation of the assembly process.3.The Future: We will address shortcomings of the prevailing methods and postulate potential improvements to better access biologically-relevant and otherwise interesting oligosaccharides to advance the glycosciences.