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Synthesis 2018; 50(14): 2631-2654
DOI: 10.1055/s-0037-1609735
DOI: 10.1055/s-0037-1609735
review
Synthesis of Lipid-Linked Oligosaccharides (LLOs) and Their Phosphonate Analogues as Probes To Study Protein Glycosylation Enzymes
This work was financially supported by the Swiss National Science Foundation (Synergia grant no. CRSII3_147632).Further Information
Publication History
Received: 23 February 2018
Accepted after revision: 04 April 2018
Publication Date:
26 June 2018 (online)
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
-
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