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, Inhaltsverzeichnis

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

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

› Institutsangaben

Abstract

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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

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Referenzen

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