Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_140624

• Article ID: 5052
  Vinogradov E, St Michael F, Cox AD "The structure of the LPS O-chain of Fusobacterium nucleatum strain 25586 containing two novel monosaccharides, 2-acetamido-2,6-dideoxy-L-altrose and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid" - Carbohydrate Research (2017) 10-15
  

  Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. Recently, it has been gaining attention as a potential causative agent for colorectal cancer and is strongly linked with pregnancy complications including pre-term and still births. Little is known about the virulence factors of this organism, and thus we have initiated studies to examine the bacterium's surface glycochemistry. We isolated lipopolysaccharide (LPS) from F. nucleatum strain 25586 and purified and performed structural analysis on the O-antigen polysaccharide. The polysaccharide contained two novel sugars, 2-acetamido-2,6-dideoxy-l-altrose (l-6dAltNAc) and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid (Non5Am), which was tentatively assigned the l-glycero-l-gluco configuration. The polysaccharide was found to have a trisaccharide repeating unit, which is phosphorylated with phosphocholine (PCho), and the following structure was established: -[-4-β-Nonp5Am-4-α-l-6dAltpNAc3PCho-3-β-d-QuipNAc-]- We propose the trivial name 'fusaminic acid' for the novel nonulosonic acid. It is the first occurrence of a 9-deoxynonulosonic acid with a hydroxyl group at C-7, which is occupied by an amino group in all monosaccharides of this class described so far.

  Lipopolysaccharide, NMR, structure, Fusobacterium, Fusobacterium nucleatum, Fusaminic acid

  NCBI PubMed ID: 28135570
  Publication DOI: 10.1016/j.carres.2017.01.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Evgeny.Vinogradov@nrc-cnrc.gc.ca
  Institutions: Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON K1A 0R6, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, GC-MS, de-O-acylation, sugar analysis, acid hydrolysis, anion-exchange chromatography, HPLC, GPC, HF treatment, acetylation
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 11979 (all data & tools)
• Article ID: 5516
  Wei R, Liu H, Li X "De novo synthesis of novel bacterial monosaccharide fusaminic acid" - The Journal of Antibiotics 72(6) (2019) 420-431
  

  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.

  synthesis, structure, O-antigen, nonulosonic acid, virulence factor, Fusobacterium nucleatum, Fusaminic acid

  NCBI PubMed ID: 30903099
  Publication DOI: 10.1038/s41429-019-0170-3
  Journal NLM ID: 0151115
  Publisher: London: Nature Publishing Group
  Correspondence: Xuechen Li
  Institutions: Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong, P. R. China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, optical rotation measurement, HR-ESI-MS, flash chromatography
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 1141 (all data & tools)

Show legend Show as text

Structure type: monomer
Aglycon: (1->4) O-antigen (ID 11979)
Compound class: O-polysaccharide, O-antigen

• Article ID: 5052
  Vinogradov E, St Michael F, Cox AD "The structure of the LPS O-chain of Fusobacterium nucleatum strain 25586 containing two novel monosaccharides, 2-acetamido-2,6-dideoxy-L-altrose and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid" - Carbohydrate Research (2017) 10-15
  

  Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. Recently, it has been gaining attention as a potential causative agent for colorectal cancer and is strongly linked with pregnancy complications including pre-term and still births. Little is known about the virulence factors of this organism, and thus we have initiated studies to examine the bacterium's surface glycochemistry. We isolated lipopolysaccharide (LPS) from F. nucleatum strain 25586 and purified and performed structural analysis on the O-antigen polysaccharide. The polysaccharide contained two novel sugars, 2-acetamido-2,6-dideoxy-l-altrose (l-6dAltNAc) and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid (Non5Am), which was tentatively assigned the l-glycero-l-gluco configuration. The polysaccharide was found to have a trisaccharide repeating unit, which is phosphorylated with phosphocholine (PCho), and the following structure was established: -[-4-β-Nonp5Am-4-α-l-6dAltpNAc3PCho-3-β-d-QuipNAc-]- We propose the trivial name 'fusaminic acid' for the novel nonulosonic acid. It is the first occurrence of a 9-deoxynonulosonic acid with a hydroxyl group at C-7, which is occupied by an amino group in all monosaccharides of this class described so far.

  Lipopolysaccharide, NMR, structure, Fusobacterium, Fusobacterium nucleatum, Fusaminic acid

  NCBI PubMed ID: 28135570
  Publication DOI: 10.1016/j.carres.2017.01.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Evgeny.Vinogradov@nrc-cnrc.gc.ca
  Institutions: Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON K1A 0R6, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, GC-MS, de-O-acylation, sugar analysis, acid hydrolysis, anion-exchange chromatography, HPLC, GPC, HF treatment, acetylation
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 12261 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_140624

• Article ID: 5052
  Vinogradov E, St Michael F, Cox AD "The structure of the LPS O-chain of Fusobacterium nucleatum strain 25586 containing two novel monosaccharides, 2-acetamido-2,6-dideoxy-L-altrose and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid" - Carbohydrate Research (2017) 10-15
  

  Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. Recently, it has been gaining attention as a potential causative agent for colorectal cancer and is strongly linked with pregnancy complications including pre-term and still births. Little is known about the virulence factors of this organism, and thus we have initiated studies to examine the bacterium's surface glycochemistry. We isolated lipopolysaccharide (LPS) from F. nucleatum strain 25586 and purified and performed structural analysis on the O-antigen polysaccharide. The polysaccharide contained two novel sugars, 2-acetamido-2,6-dideoxy-l-altrose (l-6dAltNAc) and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid (Non5Am), which was tentatively assigned the l-glycero-l-gluco configuration. The polysaccharide was found to have a trisaccharide repeating unit, which is phosphorylated with phosphocholine (PCho), and the following structure was established: -[-4-β-Nonp5Am-4-α-l-6dAltpNAc3PCho-3-β-d-QuipNAc-]- We propose the trivial name 'fusaminic acid' for the novel nonulosonic acid. It is the first occurrence of a 9-deoxynonulosonic acid with a hydroxyl group at C-7, which is occupied by an amino group in all monosaccharides of this class described so far.

  Lipopolysaccharide, NMR, structure, Fusobacterium, Fusobacterium nucleatum, Fusaminic acid

  NCBI PubMed ID: 28135570
  Publication DOI: 10.1016/j.carres.2017.01.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Evgeny.Vinogradov@nrc-cnrc.gc.ca
  Institutions: Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON K1A 0R6, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, GC-MS, de-O-acylation, sugar analysis, acid hydrolysis, anion-exchange chromatography, HPLC, GPC, HF treatment, acetylation
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 12262 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen

• Article ID: 5052
  Vinogradov E, St Michael F, Cox AD "The structure of the LPS O-chain of Fusobacterium nucleatum strain 25586 containing two novel monosaccharides, 2-acetamido-2,6-dideoxy-L-altrose and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid" - Carbohydrate Research (2017) 10-15
  

  Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. Recently, it has been gaining attention as a potential causative agent for colorectal cancer and is strongly linked with pregnancy complications including pre-term and still births. Little is known about the virulence factors of this organism, and thus we have initiated studies to examine the bacterium's surface glycochemistry. We isolated lipopolysaccharide (LPS) from F. nucleatum strain 25586 and purified and performed structural analysis on the O-antigen polysaccharide. The polysaccharide contained two novel sugars, 2-acetamido-2,6-dideoxy-l-altrose (l-6dAltNAc) and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid (Non5Am), which was tentatively assigned the l-glycero-l-gluco configuration. The polysaccharide was found to have a trisaccharide repeating unit, which is phosphorylated with phosphocholine (PCho), and the following structure was established: -[-4-β-Nonp5Am-4-α-l-6dAltpNAc3PCho-3-β-d-QuipNAc-]- We propose the trivial name 'fusaminic acid' for the novel nonulosonic acid. It is the first occurrence of a 9-deoxynonulosonic acid with a hydroxyl group at C-7, which is occupied by an amino group in all monosaccharides of this class described so far.

  Lipopolysaccharide, NMR, structure, Fusobacterium, Fusobacterium nucleatum, Fusaminic acid

  NCBI PubMed ID: 28135570
  Publication DOI: 10.1016/j.carres.2017.01.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Evgeny.Vinogradov@nrc-cnrc.gc.ca
  Institutions: Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON K1A 0R6, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, GC-MS, de-O-acylation, sugar analysis, acid hydrolysis, anion-exchange chromatography, HPLC, GPC, HF treatment, acetylation
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 12263 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide, O-antigen

• Article ID: 5052
  Vinogradov E, St Michael F, Cox AD "The structure of the LPS O-chain of Fusobacterium nucleatum strain 25586 containing two novel monosaccharides, 2-acetamido-2,6-dideoxy-L-altrose and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid" - Carbohydrate Research (2017) 10-15
  

  Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. Recently, it has been gaining attention as a potential causative agent for colorectal cancer and is strongly linked with pregnancy complications including pre-term and still births. Little is known about the virulence factors of this organism, and thus we have initiated studies to examine the bacterium's surface glycochemistry. We isolated lipopolysaccharide (LPS) from F. nucleatum strain 25586 and purified and performed structural analysis on the O-antigen polysaccharide. The polysaccharide contained two novel sugars, 2-acetamido-2,6-dideoxy-l-altrose (l-6dAltNAc) and a 5-acetimidoylamino-3,5,9-trideoxy-gluco-non-2-ulosonic acid (Non5Am), which was tentatively assigned the l-glycero-l-gluco configuration. The polysaccharide was found to have a trisaccharide repeating unit, which is phosphorylated with phosphocholine (PCho), and the following structure was established: -[-4-β-Nonp5Am-4-α-l-6dAltpNAc3PCho-3-β-d-QuipNAc-]- We propose the trivial name 'fusaminic acid' for the novel nonulosonic acid. It is the first occurrence of a 9-deoxynonulosonic acid with a hydroxyl group at C-7, which is occupied by an amino group in all monosaccharides of this class described so far.

  Lipopolysaccharide, NMR, structure, Fusobacterium, Fusobacterium nucleatum, Fusaminic acid

  NCBI PubMed ID: 28135570
  Publication DOI: 10.1016/j.carres.2017.01.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Evgeny.Vinogradov@nrc-cnrc.gc.ca
  Institutions: Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON K1A 0R6, Canada
  Methods: 13C NMR, 1H NMR, GLC-MS, GC-MS, de-O-acylation, sugar analysis, acid hydrolysis, anion-exchange chromatography, HPLC, GPC, HF treatment, acetylation
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 12264 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: polysaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_140624

• Article ID: 6513
  Zhu J, Li M, Li J, Wu J "Sialic acid metabolism of oral bacteria and its potential role in colorectal cancer and Alzheimer’s disease" - Carbohydrate Research 541 (2024) ID 109172
  

  Sialic acid metabolism in oral bacteria is a complex process involving nutrient acquisition, immune evasion, cell surface modification, and the production of metabolites that contribute to bacterial persistence and virulence in the oral cavity. In addition to causing various periodontal diseases, certain oral pathogenic bacteria, such as Porphyromonas gingivalis, Tannerella forsythia, and Fusobacterium nucleatum, can induce inflammatory reactions and influence the immunity of host cells. These associations with host cells are linked to various diseases, particularly colorectal cancer and Alzheimer's disease. Sialic acid can be found in the host oral mucosa, saliva, or food residues in the oral cavity, and it may promote the colonization of oral bacteria and contribute to disease development. This review aims to summarize the role of sialic acid metabolism in oral bacteria and discuss its effect on the pathogenesis of colorectal cancer and Alzheimer's disease

  Porphyromonas gingivalis, Fusobacterium nucleatum, Alzheimer's disease, colorectal cancer, sialic acid metabolism

  NCBI PubMed ID: 38823062
  Publication DOI: 10.1016/j.carres.2024.109172
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: kinowu@jiangnan.edu.cn
  Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China
  
   
  
  Fusobacterium nucleatum 25586
  CSDB ID 15656 (all data & tools)