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De novo synthesis of novel bacterial monosaccharide fusaminic acid

Abstract

Fusobacterium nucleatum is an oral bacteria related to various types of diseases. As Gram-negative bacteria, lipopolysaccharide (LPS) of Fusobacterium nucleatum could be a potential virulence factor. Recently, the structure of O-antigen in LPS of Fusobacterium nucleatum strain 25586 was elucidated to contain a trisaccharide repeating unit -(4-β-Nonp5Am-4-α-L-6dAltpNAc3PCho-3-β-D-QuipNAc)-. The nonulosonic acid characterized as 5-acetamidino-3,5,9-trideoxy-L-glycero-L-gluco-non-2-ulosonic acid (named as fusaminic acid), and 2-acetamido-2,6-dideoxy-L-altrose are the novel monosaccharides isolated. Herein we report the de novo synthesis of 5-N-acetyl fusaminic acid and the thioglycoside derivative in order to further investigate the biological significance of nonulosonic acids for bacterial pathogenesis.

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Acknowledgements

This work was supported by the Research Grants Council of Hong Kong (17305615, 17309616, C5026–16G) and the University Grants Committee of Hong Kong (Grant AoE/P-705/16).

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Correspondence to Xuechen Li.

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The authors declare that they have no conflict of interest.

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Dedication: This is dedicated to Professor Samuel. J. Danishefsky for his great scientific contribution to total synthesis of highly complex and biologically important natural products.

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Supplementary information

SI De novo synthesis of novel bacteria monosaccharide fusaminic acid

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