De novo synthesis of novel bacterial monosaccharide fusaminic acid

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 t...

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Bibliographic Details
Published inJournal of antibiotics Vol. 72; no. 6; pp. 420 - 431
Main Authors Wei, Ruohan, Liu, Han, Li, Xuechen
Format Journal Article
LanguageEnglish
Published LONDON Springer Nature 01.06.2019
Nature Publishing Group
Subjects
Acids
Bacteria
Bacteria - chemistry
Biotechnology & Applied Microbiology
Carbohydrate Conformation
Fusobacterium nucleatum - chemistry
Immunology
Ketoses - chemical synthesis
Ketoses - chemistry
Life Sciences & Biomedicine
Microbiology
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
Pharmacology & Pharmacy
Science & Technology
FUSOBACTERIUM-NUCLEATUM
LEGIONAMINIC ACID
PERIODONTITIS
PORPHYROMONAS-GINGIVALIS
PSEUDAMINIC ACID
ISOCYANOACETATE
FADA
ALDOL REACTIONS
ALDEHYDES
SERUM ANTIBODIES
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Summary: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-beta-Nonp5Am-4-alpha-L-6dAltpNAc3PCho-3-beta-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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ISSN:0021-8820
1881-1469
DOI:10.1038/s41429-019-0170-3