Synthesis of Lipid-Linked Oligosaccharides (LLOs) and Their Phosphonate Analogues as Probes To Study Protein Glycosylation Enzymes

Jérémy M. Boilevin; Jean-Louis Reymond

doi:10.1055/s-0037-1609735

Synthesis, Table of Contents

Synthesis 2018; 50(14): 2631-2654
DOI: 10.1055/s-0037-1609735

review

Synthesis of Lipid-Linked Oligosaccharides (LLOs) and Their Phosphonate Analogues as Probes To Study Protein Glycosylation Enzymes

Authors

Jérémy M. Boilevin

Department of Chemistry and Biochemistry,University of Bern, Freiestrasse 3, 3012 Bern, Switzerland Email: jean-louis.reymond@dcb.unibe.ch
Jean-Louis Reymond *

Department of Chemistry and Biochemistry,University of Bern, Freiestrasse 3, 3012 Bern, Switzerland Email: jean-louis.reymond@dcb.unibe.ch

Abstract

All articles of this category

Abstract

Here we review chemical and chemoenzymatic methods for the synthesis of lipid-linked oligosaccharides (LLOs) and their phosphonate analogues, which serve as substrates and inhibitors to investigate the structure and mechanism of protein N-glycosylation enzymes. We emphasize how to overcome the challenges pertaining to the instability and difficult physicochemical properties of this class of compounds.

1 Introduction

2 LLO Syntheses

2.1 Glycosyl Phosphate Syntheses

2.2 Glycosyl Phosphonates

2.3 Lipid Elongation

2.4 Lipid Phosphates

2.5 Coupling Reaction Strategies

3 Chemoenzymatic Synthesis of Elongated LLOs

4 Biological Properties of Synthetic LLOs

5 Conclusion

Key words

carbohydrates - polyprenols - diphosphates - phosphonates - glycosides - lipid-linked oligosaccharides

Full Text

References

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