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Book Chapter

Orthogonally protected building blocks for automated glycan assembly

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Pfrengle,  Fabian
Fabian Pfrengle, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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

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Citation

Pfrengle, F., & Seeberger, P. H. (2018). Orthogonally protected building blocks for automated glycan assembly. In Protecting Groups (pp. 451-471). Weinheim: Wiley-VCH.


Cite as: https://hdl.handle.net/21.11116/0000-0006-DB42-9
Abstract
Summary Following an introduction to solid-phase carbohydrate chemistry and automated glycan assembly, we discuss the specific requirements for protecting groups (PGs) used in solid-phase chemistry. Besides routinely applied permanent and temporary PGs, specialized solutions for specific problems such as the introduction of β-mannosides are covered. Based on the available orthogonal PGs, a general strategy for the design of suitable building blocks for a given oligosaccharide target is proposed. A set of “approved” monosaccharide building blocks that have been successfully applied in the assembly of various oligosaccharides is presented. Exemplary syntheses of mammalian, microbial, and plant oligosaccharides are described to demonstrate the importance of choosing suitable orthogonally protected building blocks. Finally, an update on commercial automated oligosaccharide synthesizers is provided as well as a short outlook on the chances and challenges of automated glycan assembly.