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Pathogen-Associated Molecular Patterns: The Synthesis of Heptose Phosphates and Derivatives
Synthesis ( IF 2.6 ) Pub Date : 2021-09-06 , DOI: 10.1055/s-0040-1720179
Janelle Sauvageau , Dean Williams , Mohammad P. Jamshidi

Lipopolysaccharide biosynthesis metabolites, such as d-glycero-β-d-manno-heptopyranosyl 1,7-diphosphate, d-glycero-β-d-manno-heptopyranosyl phosphate, and adenosine 5′-(l-glycero-β-d-manno-heptopyranosyl)diphosphate, have been found to activate NF-κB via alpha-kinase 1 and TRAF-interacting protein with forkhead associated domain. This axis has been determined as a novel pathway of innate immunity yet to be targeted for immunomodulatory treatment approaches. Key in understanding this new axis has been the ability to synthesize these metabolites. The design of synthetic analogues and probes have also been published not only to design new drugs, but also to gain insight into the mechanism of action for these compounds. The focus of the present review is the synthesis of heptose phosphate metabolites­ as well as synthetic analogues and probes.

1 Introduction

2 Synthesis of d-glycero-d-manno-Heptose

2.1 Using d-Mannose as Starting Material

2.2 Using d-Ribose as Starting Material

2.3 Using 2,2-Dimethyl-1,3-dioxan-5-one as Starting Material

3 Synthesis of l-glycero-d-manno-Heptose

3.1 Using d-Mannose as Starting Material

3.2 Using 2,2-Dimethyl-1,3-dioxan-5-one as Starting Material

3.3 Using l-Lyxose as Starting Material

4 Synthesis of Heptose Phosphates

4.1 Synthesis of d-glycero-β-d-manno-Heptose 1,7-Diphosphate

4.2 Synthesis of Heptose Phosphate Derivatives

4.2.1 Development of Scaffolds for Conjugation

4.2.2 Development of Heptose Phosphates Derivatives for Cell Intake and Metabolic Stability

5 Conclusion and Outlook



中文翻译:

病原体相关分子模式:磷酸庚糖及其衍生物的合成

脂多糖生物合成代谢物,如 d-甘油-β-d-甘露糖-吡喃基1,7-二磷酸,d-甘油-β-d-甘露糖-吡喃庚糖基磷酸酯和腺苷 5'-(-甘油-β-d-甘露糖-吡喃基)二磷酸,已被发现通过 α-激酶 1 和具有叉头相关结构域的 TRAF 相互作用蛋白激活 NF-κB。该轴已被确定为一种新的先天免疫途径,尚未成为免疫调节治疗方法的目标。理解这个新轴的关键是合成这些代谢物的能力。合成类似物和探针的设计也已经发表,不仅可以设计新药,还可以深入了解这些化合物的作用机制。本综述的重点是磷酸庚糖代谢物以及合成类似物和探针的合成。

1 简介

2 合成 d-甘油-d-甘露糖-

2.1 使用 d- 甘露糖作为起始材料

2.2 使用 d-核糖作为起始材料

2.3 使用 2,2-Dimethyl-1,3-dioxan-5-one 作为原料

3 合成 -甘油-d-甘露糖-

3.1 使用 d- 甘露糖作为起始材料

3.2 使用 2,2-Dimethyl-1,3-dioxan-5-one 作为原料

3.3 使用 - 来苏糖作为起始材料

4 磷酸庚糖的合成

4.1 合成 d-甘油-β-d-甘露糖-糖 1,7-二磷酸

4.2 磷酸庚糖衍生物的合成

4.2.1 共轭支架的开发

4.2.2 用于细胞摄取和代谢稳定性的磷酸庚糖衍生物的开发

5 结论与展望

更新日期:2021-09-07
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