This review covers data on composition and structure of lipid A, core, and O-polysaccharide of the known lipopolysaccharides from Gram-negative bacteria. The relationship between the structure and biological activity of lipid A is discussed. The data on roles of core and O-polysaccharide in biological activities of lipopolysaccharides are presented. The structural homology of some oligosaccharide sequences of lipopolysaccharides to gangliosides of human cell membranes is considered.

core, Lipooligosaccharide, O-antigen, lipid A, gangliosides, cytokines, lipopolysaccharide (endotoxin)

NCBI PubMed ID: 20618127
Publication DOI: 10.1134/S0006297910040012
Journal NLM ID: 0376536
Publisher: Nauka/Interperiodica
Correspondence: kabanovd1rambler.ru
Institutions: Institute of Basic Biological Problems, Russian Academy of Sciences, Pushchino, Russia
 

• Compound ID: 9004
  

  a-Galp-(1-4)-+ | a-GalpA-(1-5)-Kdop-(2-4)-+ | a-GalpA-(1-4)-+ | | | Fucp-(1-?)-Manp-(1-?)-QuipNAc-(1-?)-Kdop-(2-6)-a-Galp-(1-6)-a-Manp-(1-5)-Kdop-(2--/lipid A/

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GTC:G03173PE
  
   
  
  Rhizobium etli CE3
  CSDB ID 25678 (all data & tools)
• Compound ID: 9022
  

  a-6dTalp3Me-(1-3)-+ | -4)-a-D-GlcpA-(1-4)-a-L-Fucp-(1-

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  Structure type: polymer biological repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G32020LR, GlycomeDB:37875
  
   
  
  Rhizobium etli CE3
  CSDB ID 25706 (all data & tools)
• Compound ID: 9023
  

  a-Fucp2Me3Me4Me-(1-4)-Subst-(1-3)-a-L-Fucp-(1-3)-b-D-Manp-(1-3)-b-QuipNAc-(1-4)-a-Kdop-(2--/core-lipid A/ Subst = O-antigen ID 25706

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  Structure type: oligomer
  Aglycon: core-lipid A
  Compound class: O-polysaccharide, O-antigen
  
   
  
  Rhizobium etli CE3
  CSDB ID 25707 (all data & tools)
• Compound ID: 172
  

  b-D-Glcp-(1-2)-+ | a-D-Galp-(1-2)-+ | | | a-Neup5Ac-(2-3)-+ | | /Variants 0/-+ | | | | b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ | b-D-Glcp-(1-4)-+ /Variants 0/ is: P-6)- OR (exclusively) EtN-(1--P--6)--

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide, LPS
  
   
  
  Campylobacter jejuni NCTC 11168
  CSDB ID 25684 (all data & tools)
• Compound ID: 9024
  

  -4)-a-Neup5Ac-(2-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1-

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  Structure type: polymer chemical repeating unit
  Aglycon: core-lipid A
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G41603RX, GlycomeDB:25560
  
   
  
  Salmonella enterica sv. Toucra O48
  CSDB ID 25708 (all data & tools)
• Compound ID: 1590
  

  b-D-GlcpNAc-(1-4)-+ | EtN-(1--P--6)--+ | | | L-Ala-(2-6)-+ | | | | | -3)-a-D-GalpA-(1-3)-b-D-GlcpNAc-(1-3)-b-D-GlcpA-(1- | L-Lys-(2-6)-+

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  Structure type: polymer chemical repeating unit
  Compound class: O-polysaccharide, O-antigen
  
   
  
  Proteus mirabilis O27
  CSDB ID 25704 (all data & tools)
• Compound ID: 9021
  

  D-Rib-ol-(5--P--3)--+ EtN-(1--P--6)--+ | | -2)-b-D-Galp-(1-3)-a-D-GlcpNAc-(1-3)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1-

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  Structure type: polymer chemical repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G50608KJ
  
   
  
  Proteus mirabilis D52
  CSDB ID 25701 (all data & tools)
• Compound ID: 581
  

  -4)-a-L-GalpNAc3NAcA-(1-

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  Structure type: homopolymer
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G17747AL, GlycomeDB:26665
  
   
  
  Bordetella bronchiseptica 110H, Bordetella bronchiseptica Bp5132
  CSDB ID 25690 (all data & tools)
• Compound ID: 9000
  

  b-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-+ /Variants 0/-+ a-Kdop-(2-4)-+ | | | /Variants 1/-a-GlcpN-(1-4)-a-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ /Variants 0/ is: b-GalpA-(1-6)-b-Glcp-(1-4)- OR (exclusively) b-Glcp-(1-4)- /Variants 1/ is: D-gro-a-D-manHepp-(1-4)-a-Kdop-(2-6)- OR (exclusively) a-Kdop-(2-6)-

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  
   
  
  Klebsiella pneumoniae O3
  CSDB ID 25672 (all data & tools)
• Compound ID: 9017
  

  -2)-b-D-Ribf-(1-4)-a-D-Galp-(1-

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  Structure type: polymer biological repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G71407UU, GlycomeDB:3999
  
   
  
  Klebsiella pneumoniae O4
  CSDB ID 25696 (all data & tools)
• Compound ID: 9018
  

  a-Kdop-(2-2)-Subst Subst = O-antigen (ID 25696)

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  Structure type: oligomer
  Compound class: O-polysaccharide, O-antigen
  
   
  
  Klebsiella pneumoniae O4
  CSDB ID 25697 (all data & tools)
• Compound ID: 9019
  

  b-Kdop-(2-3)-a-L-Rhap-(1-3)-Subst Subst = O-antigen (ID 25699)

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  Structure type: oligomer
  Compound class: O-polysaccharide, O-antigen
  
   
  
  Klebsiella pneumoniae O12
  CSDB ID 25698 (all data & tools)
• Compound ID: 9020
  

  -3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-

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  Structure type: suggested polymer biological repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G63032KR, GlycomeDB:3573
  
   
  
  Klebsiella pneumoniae O12
  CSDB ID 25699 (all data & tools)
• Compound ID: 8999
  

  b-D-Glcp-(1-2)-+ | a-D-GalpN-(1-2)-+ | | | Sug-(1-3)-b-D-QuipNAc-(1-4)-b-D-Manp-(1-4)-a-D-Manp-(1-5)-a-Kdop-(2--/lipid A/ | a-D-Glcp-(1-3)-+ Sug = modified ??GalNA

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  
   
  
  Francisella tularensis ATCC 29684
  CSDB ID 25297 (all data & tools)
• Compound ID: 9005
  

  L-gro-a-D-manHepp-(1-7)-+ b-Glcp-(1-4)-+ b-L-Arap4N-(1-8)-+ | | | L-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ | /Variants 0/-+ /Variants 0/ is: Kop-(2-4)- OR (exclusively) Kdop-(2-4)-

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  
   
  
  Serratia marcescens 111R
  CSDB ID 25679 (all data & tools)
• Compound ID: 8623
  

  b-D-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-+ | D-gro-a-D-manHepp-(1-2)-+ | b-D-Glcp-(1-4)-+ b-L-Arap4N-(1-8)-+ | | | | D-gro-a-D-manHepp-(1-6)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ | | EtN-(1--P--6)--+ a-Kdop-(2-4)-+

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide, LOS, LPS
  Reference(s) to other database(s): GTC:G74966LS
  
   
  
  Proteus mirabilis R110/1959
  CSDB ID 25677 (all data & tools)
• Compound ID: 9010
  

  a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+ | a-D-Glcp-(1-3)-+ | | | /Variants 0/-+ | | a-Kdop-(2-4)-+ | | | | EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ | a-D-GlcpNAc-(1-2)-+ /Variants 0/ is: EtN-(1--P--7)-- OR (exclusively) Gly-(1-7)-

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  
   
  
  Neisseria meningitidis L2
  CSDB ID 25685 (all data & tools)
• Compound ID: 3917
  

  a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ | Subst-(1-7)-+ | P-7)-+ | | | a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ Subst = O-antigen

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  
   
  
  Helicobacter pylori 26695
  CSDB ID 25671 (all data & tools)
• Compound ID: 9015
  

  a-L-Fucp-(1-2)-Subst-(1-3)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp Subst = O-antigen (ID22695)

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  Structure type: oligomer
  Compound class: LPS
  
   
  
  Helicobacter pylori 26695
  CSDB ID 25694 (all data & tools)
• Compound ID: 9016
  

  a-L-Fucp-(1-3)-+ | -3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-

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  Structure type: polymer biological repeating unit
  Trivial name: Lewis X epitope
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G79959AY, GlycomeDB:17105
  
   
  
  Helicobacter pylori 26695
  CSDB ID 25695 (all data & tools)
• Compound ID: 1259
  

  a-D-Galp-(1-2)-+ | -7)-a-Neup5Ac-(2-3)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1-

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  Structure type: suggested polymer biological repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G32692RT, GlycomeDB:6888
  
   
  
  Escherichia coli O56
  CSDB ID 25691 (all data & tools)
• Compound ID: 4728
  

  -4)-a-D-Galp-(1-4)-a-Neup5Ac7Ac9Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-

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  Structure type: suggested polymer biological repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G18884UL, GlycomeDB:3545
  
   
  
  Escherichia coli O104
  CSDB ID 25692 (all data & tools)
• Compound ID: 1586
  

  S,R-CetLys-(2-6)-a-D-GalpA-(1-4)-+ | -3)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-

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  Structure type: polymer chemical repeating unit
  Compound class: O-polysaccharide, O-antigen
  
   
  
  Proteus mirabilis O13
  CSDB ID 25702 (all data & tools)
• Compound ID: 7915
  

  a-L-Fucp-(1-4)-+ | -3)-b-D-GlcpNAc-(1-4)-a-D-GalpA-(1-3)-a-L-Fucp-(1-3)-b-D-GlcpNAc-(1-

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  Structure type: polymer biological repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G59020TN, GlycomeDB:28129
  
   
  
  Escherichia coli O159
  CSDB ID 25693 (all data & tools)
• Compound ID: 1752
  

  a-D-Glcp-(1-2)-b-D-Galp-(1-4)-+ | -3)-a-D-GlcpNAc-(1-4)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1-

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  Structure type: polymer chemical repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G10235UA, GlycomeDB:27451
  
   
  
  Proteus mirabilis O20
  CSDB ID 25703 (all data & tools)
• Compound ID: 9002
  

  a-D-Glcp-(1-4)-+ | a-D-Glcp-(1-6)-+ | P-4)-+ P-2)-+ a-Kdop-(2-4)-+ | | | | | a-L-Rhap-(1-3)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp7Cm-(1-5)-a-Kdop-(2--/lipid A/ | | | L-Ala-(1-2)-+ P-6)-+ P-4)-+

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GlycomeDB:37870
  
   
  
  Pseudomonas aeruginosa 2192
  CSDB ID 25675 (all data & tools)
• Compound ID: 9003
  

  a-L-Rhap-(1-6)-a-D-Glcp-(1-4)-+ P-4)-+ P-2)-+ a-Kdop-(2-4)-+ | | | | a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp7Cm-(1-5)-a-Kdop-(2--/lipid A/ | | | L-Ala-(1-2)-+ P-6)-+ P-4)-+

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GlycomeDB:37871
  
   
  
  Pseudomonas aeruginosa 2192
  CSDB ID 25676 (all data & tools)
• Compound ID: 9014
  

  a-D-Glcp-(1-4)-+ | LIP-(1-3)-+ | | | -2)-b-D-Quip3N-(1-6)-a-D-Glcp-(1-4)-b-D-GlcpA-(1-3)-a-D-GlcpNAc-(1-

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  Structure type: polymer biological repeating unit
  Compound class: O-polysaccharide
  Reference(s) to other database(s): GlycomeDB:33591
  
   
  
  Hafnia alvei 1185
  CSDB ID 25689 (all data & tools)
• Compound ID: 9007
  

  P-4)-+ | a-D-Glcp-(1--P--3)--L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/

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  Structure type: fragment of a bigger structure
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GTC:G39696RK, GlycomeDB:37872
  
   
  
  Alteromonas addita KMM 3600T
  CSDB ID 25681 (all data & tools)
• Compound ID: 9006
  

  D-GroA-(2--P--7)--+ /Variants 0/-+ | | a-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-5)-a-Kdop8N-(2--/lipid A/ | L-gro-a-D-manHepp-(1-2)-+ /Variants 0/ is: P-4)- OR (exclusively) EtN-(1---P---P---4)-

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  
   
  
  Shewanella pacifica KMM 3772
  CSDB ID 25680 (all data & tools)
• Compound ID: 9009
  

  L-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-+ | b-D-QuipNAc-(1-3)-a-L-Rhap-(1-2)-+ | a-Kop-(2-4)-+ | | | b-D-Glcp-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-L-Rhap-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ | L-gro-a-D-manHepp-(1-7)-+

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GTC:G03152EV, GlycomeDB:37874
  
   
  
  Burkholderia multivorans
  CSDB ID 25683 (all data & tools)
• Compound ID: 7182
  

  a-D-GalpA-(1-3)-+ b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+ | | | b-D-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GTC:G63317BP, GlycomeDB:27951
  
   
  
  Klebsiella pneumoniae 52145 O1:K12
  CSDB ID 25673 (all data & tools)
• Compound ID: 9001
  

  b-D-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-+ b-D-Glcp-(1-4)-+ | | b-D-Glcp-(1-6)-a-D-Glcp-(1-4)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GTC:G36534XJ, GlycomeDB:37869
  
   
  
  Klebsiella pneumoniae 52145 O1:K12
  CSDB ID 25674 (all data & tools)
• Compound ID: 9008
  

  Arap4N-(1-?)-a-Kop-(2-4)-+ | L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-7)-+ | | | a-D-Glcp-(1-6)-+ | b-D-Glcp-(1-4)-+ | | | | | a-L-Rhap-(1-3)-b-D-QuipNAc-(1-7)-L-gro-a-D-manHepp-(1-2)-a-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/

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  Structure type: oligomer
  Aglycon: lipid A
  Compound class: core oligosaccharide
  Reference(s) to other database(s): GTC:G17312AV, GlycomeDB:37873
  
   
  
  Burkholderia cenocepacia ET-12 (J2315)
  CSDB ID 25682 (all data & tools)
• Compound ID: 9011
  

  a-D-Glcp-(1-4)-+ | a-D-Glcp-(1-6)-+ | P-6)-+ EtN-(1---P---P---2)-+ a-Kdop-(2-4)-+ | | | | | a-L-Rhap2Ac-(1-4)-a-L-GalpNAcA-(1-3)-a-D-QuipNAc-(1-3)-Subst-(1-3)-a-L-Rhap2Ac-(1-3)-a-L-GalpNAcA-(1-3)-b-D-QuipNAc-(1-3)-a-L-Rhap-(1-3)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ | | L-Ala-(1-2)-+ P-4)-+ Subst = O-antigen (ID 25687)

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  Structure type: oligomer
  Aglycon: lipid A
  Trivial name: S-LPS
  Compound class: LPS
  
   
  
  Pseudomonas aeruginosa O10 immunotype 5
  CSDB ID 25686 (all data & tools)
• Compound ID: 9012
  

  -3)-a-L-Rhap2Ac-(1-3)-a-L-GalpNAcA-(1-3)-a-D-QuipNAc-(1-

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  Structure type: polymer biological repeating unit
  Aglycon: core oligosaccharide ID 25686
  Compound class: O-antigen
  Reference(s) to other database(s): GTC:G19927HQ, GlycomeDB:27544
  
   
  
  Pseudomonas aeruginosa O10 immunotype 5
  CSDB ID 25687 (all data & tools)
• Compound ID: 9013
  

  a-D-Glcp-(1-4)-+ | a-D-Glcp-(1-6)-+ | P-6)-+ EtN-(1---P---P---2)-+ a-Kdop-(2-4)-+ | | | | | a-L-Rhap2Ac-(1-4)-a-L-GalpNAcA-(1-3)-b-D-QuipNAc-(1-3)-a-L-Rhap-(1-3)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ | | L-Ala-(1-2)-+ P-4)-+

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  Structure type: oligomer
  Aglycon: lipid A
  Trivial name: SR-LPS
  Compound class: core oligosaccharide with O-unit
  
   
  
  Pseudomonas aeruginosa O10 immunotype 5
  CSDB ID 25688 (all data & tools)
• Compound ID: 2570
  

  L-Lys-(2-6)-a-D-GalpA-(1-4)-+ | -3)-b-D-GalpNAc-(1-6)-b-D-GalpNAc-(1-4)-b-D-GlcpA-(1-

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  Structure type: polymer chemical repeating unit
  Compound class: O-polysaccharide, O-antigen
  
   
  
  Proteus mirabilis G1
  CSDB ID 25700 (all data & tools)
• Compound ID: 33
  

  -4)-a-D-GalpNAcA3Ac6NH2-(1-4)-a-D-GalpNFoA6NH2-(1-3)-a-D-QuipNAc-(1-2)-a-L-Rhap-(1-

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  Structure type: polymer chemical repeating unit
  Compound class: O-polysaccharide, O-antigen
  Reference(s) to other database(s): GTC:G36772HX, GlycomeDB:25506
  
   
  
  Pseudomonas aeruginosa 170041
  CSDB ID 25705 (all data & tools)