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Synthesis 2022; 54(01): 79-91
DOI: 10.1055/s-0040-1720179
DOI: 10.1055/s-0040-1720179
short review
Pathogen-Associated Molecular Patterns: The Synthesis of Heptose Phosphates and Derivatives
The subject related to this review was funded by the Vaccine and Emerging Infections Research Initiative within the Human Health Therapeutics Research Centre at the National Research Council Canada.
Abstract
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
Key words
heptose diphosphate - heptose monophosphate - ADP-heptose - metabolites - pathogen associated molecular patternsPublikationsverlauf
Eingereicht: 28. Mai 2021
Angenommen nach Revision: 26. Juli 2021
Artikel online veröffentlicht:
06. September 2021
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