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

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

中文翻译：

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脂质连接寡糖（LLOs）的合成及其膦酸酯类似物作为研究蛋白质糖基化酶的探针

摘要

在这里，我们审查化学和化学酶法合成脂质连接的寡糖（LLOs）及其膦酸酯类似物的方法，它们可作为底物和抑制剂来研究蛋白质N-糖基化酶的结构和机理。我们强调如何克服与这类化合物的不稳定性和困难的理化性质有关的挑战。

1引言

2 LLO综合

2.1磷酸糖基酯的合成

2.2糖基膦酸酯

2.3脂质伸长

2.4磷脂脂质

2.5偶联反应策略

3化学酶法合成伸长的LLO

4合成LLO的生物学特性

5结论

在这里，我们审查化学和化学酶法合成脂质连接的寡糖（LLOs）及其膦酸酯类似物的方法，它们可作为底物和抑制剂来研究蛋白质N-糖基化酶的结构和机理。我们强调如何克服与这类化合物的不稳定性和困难的理化性质有关的挑战。

1引言

2 LLO综合

2.1磷酸糖基酯的合成

2.2糖基膦酸酯

2.3脂质伸长

2.4磷脂脂质

2.5偶联反应策略

3化学酶法合成伸长的LLO

4合成LLO的生物学特性

5结论