Lipopolysaccharide (LPS) is a crucial constituent of the outer membrane of most Gram-negative bacteria, playing a fundamental role in the protection of bacteria from environmental stress factors, in drug resistance, in pathogenesis, and in symbiosis. During the last decades, LPS has been thoroughly dissected, and massive information on this fascinating biomolecule is now available. In this Review, we will give the reader a third millennium update of the current knowledge of LPS with key information on the inherent peculiar carbohydrate chemistry due to often puzzling sugar residues that are uniquely found on it. Then, we will drive the reader through the complex and multifarious immunological outcomes that any given LPS can raise, which is strictly dependent on its chemical structure. Further, we will argue about issues that still remain unresolved and that would represent the immediate future of LPS research. It is critical to address these points to complete our notions on LPS chemistry, functions, and roles, in turn leading to innovative ways to manipulate the processes involving such a still controversial and intriguing biomolecule.
- Compound ID: 9223
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp |
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Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G01767JJ, GlycomeDB:
37903
- Compound ID: 15666
|
Subst-(1-4)-+
|
/Variants 0/-b-D-Glcp-(1-4)-+
|
/Variants 2/-+ EtN-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | | |
/Variants 1/-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/(2->6)lipid A/
|
Subst-(1-3)-+
/Variants 0/ is:
Cho-(1--P--6)--
OR (exclusively)
L-gro-D-manHepp-(1-6)-
OR (exclusively)
D-gro-D-manHepp-(1-6)-
/Variants 1/ is:
Gly-(1-3)-
OR (exclusively)
b-D-Galp-(1-3)-
OR (exclusively)
Subst-(1-3)-
OR (exclusively)
Ac-3)-
OR (exclusively)
EtN-(1-0)-?%P-3)-
/Variants 2/ is:
b-D-Galp-(1-2)-
OR (exclusively)
?%Subst-(1-2)-
Subst = H, sugar residue or OS unit |
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Structure type: oligomer
Aglycon: (2->6)lipid A
Trivial name: conserved tri-heptosyl inner core
Compound class: LOS
- Compound ID: 15667
Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15668
|
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp |
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Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15669
|
b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-+
|
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp |
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Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15670
Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15671
|
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp |
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Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15672
Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15673
Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15674
|
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp |
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Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 15675
Structure type: fragment of a bigger structure
Compound class: core oligosaccharide
- Compound ID: 528
|
b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
|
a-D-GlcpNAc-(1-2)-+ | a-Kdop-(2-4)-+
| | |
EtN-(1--P--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
Trivial name: core oligosaccharide L8
Compound class: core oligosaccharide, LOS, LPS
Reference(s) to other database(s): GTC:G66058QA
- Compound ID: 797
|
a-D-GlcpNAc-(1-2)-+
|
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
| |
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L7
Compound class: core oligosaccharide, LOS
Reference(s) to other database(s): GTC:G45549QG
- Compound ID: 6318
|
Lau-(1-3)-R-3HOMyr-(1-2)-+
|
Lau-(1-3)-R-3HOMyr-(1-2)-+ |
| |
EtN-(1---P---P---4)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1---P---P---1)-EtN
| |
R-3HOLau-(1-3)-+ |
|
R-3HOLau-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 15676
|
a-D-GlcpNAc-(1-2)-+
|
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
| |
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L3
Compound class: LOS
- Compound ID: 15677
|
a-D-GlcpNAc-(1-2)-+
|
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
| |
a-Neup5Ac-(2-6)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L1
Compound class: LOS
- Compound ID: 15678
|
a-D-GlcpNAc-(1-2)-+
|
/Variants 0/-L-gro-a-D-manHepp3Ac-(1-3)-+ a-Kdop-(2-4)-+
| |
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
EtN-(1--P--7)--
OR (exclusively)
EtN-(1--P--6)-- |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L4
Compound class: LOS
- Compound ID: 15679
|
a-D-GlcpNAc-(1-2)-+
|
/Variants 0/-L-gro-a-D-manHepp3Ac-(1-3)-+ a-Kdop-(2-4)-+
| |
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
EtN-(1--P--7)--
OR (exclusively)
EtN-(1--P--6)-- |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L9
Compound class: LOS
- Compound ID: 15680
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
|
a-D-GlcpNAc-(1-2)-+ | a-Kdop-(2-4)-+
| | |
/Variants 0/-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
a-D-Glcp-(1-3)-+
/Variants 0/ is:
EtN-(1--P--7)--
OR (exclusively)
EtN-(1--P--6)-- |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L2
Compound class: LOS
- Compound ID: 15681
|
b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
|
a-D-GlcpNAc-(1-2)-+ | a-Kdop-(2-4)-+
| | |
/Variants 0/-L-gro-a-D-manHepp3Ac-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
EtN-(1--P--7)--
OR (exclusively)
EtN-(1--P--6)-- |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: core oligosaccharide L6
Compound class: LOS
- Compound ID: 314
|
R-3HOMyr-(1-2)-+
|
Myr-(1-3)-R-3HOMyr-(1-3)-+ |
| |
Lau-(1-3)-R-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
R-3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: LPS, lipid A, glycolipid, phosphoglycolipid
- Compound ID: 1598
|
R-3HOMyr-(1-2)-+
|
R-3HOMyr-(1-3)-+ |
| |
R-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
R-3HOMyr-(1-3)-+ |
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Structure type: oligomer
Trivial name: lipid IV A, lipid IV(A)
Compound class: lipid A, glycolipid
- Compound ID: 15685
|
Pam-(1-3)-3HOMyr-(1-2)-+
|
Lau-(1-3)-3HOMyr-(1-3)-+ |
| |
Myr-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1--P--0)--?%P-1)-EtN
| |
b-L-Arap4N-(1--P--4)--+ 3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 2029
Structure type: polymer chemical repeating unit
Trivial name: i-antigen, N-acetyllactosaminoglycan, poly-(N-acetyl-b-lactosamine) chain, polylacNAc O-chain, poly(N-acetyl-b-lactosamine) chain, Poly LacNAc
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G39453SO, GlycomeDB:
15913
- Compound ID: 12637
Structure type: oligomer
Trivial name: Lewis a antigen Le(a), Lewis a antigen, Lewis A antigen Le(a)
Reference(s) to other database(s): GTC:G39023AU
- Compound ID: 12638
Structure type: oligomer
Trivial name: Lewis b antigen Le(b), Lewis b antigen, Lewis B antigen Le(b)
Reference(s) to other database(s): GTC:G00048MO
- Compound ID: 12640
Structure type: oligomer
Trivial name: Lewis Y antigen, Lewis Y antigen Le(y), Lewis y antigen Le(y)
Reference(s) to other database(s): GTC:G00052MO
- Compound ID: 12641
Structure type: oligomer
Trivial name: Lewis X antigen, Lewis X antigen Le(x), Lewis x antigen Le(x)
Reference(s) to other database(s): GTC:G00051MO
- Compound ID: 711
|
S-3HOBut-(1-7)-+
|
-4)-b-Sugp5Ac-(2-2)-S-2HOGlt-(5-4)-b-D-QuipNAc4N3Ac-(1-
Sug = 5,7,8-triamino-3,5,7,8,9-pentadeoxy-?-glycero-L-manno-non-2-ulosonic acid = SMILES CC({7}[C@@H]([C@@H]1O{2}[C@@](C(O)=O)(C{4}[C@@H]({5}[C@@H]1N)O)O)N)N |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 15662
|
b-D-Galp-(1-4)-+ L-gro-a-D-manHepp-(1-7)-+ P-4)-+ a-Kdop-(2-4)-+
| | | |
a-D-Galp-(1-2)-a-D-Galp-(1-2)-a-D-Glcp-(1-3)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop
|
P-4)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 15686
|
2HOLau-(1-3)-3HOLau-(1-2)-+
|
Lau-(1-3)-3HODco-(1-3)-+ |
| |
Lau-(1-3)-3HOLau-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1--P--1)--b-L-Arap4N
|
b-L-Arap4N-(1--P--4)--+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 15683
|
Subst2-25Ac-(1-3)-R-3HOMyr-(1-2)-+ R-3HOMyr-(1-2)-+
| |
Subst-(34-31)-Subst1-(1-3)-R-3HOLau-(1-3)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GalpA
| |
a-D-Manp-(1-6)-a-D-Manp-(1-4)-+ R-3HOLau-(1-3)-+
Subst = 34-carboxyl-bacteriohopane-32,33-diol = SMILES CC(CCC{32}(O){33}C(O){34}C(O)=O)C1C2CC[C@@]3(C)[C@]4(C)CCC5C(C)(C)CCC[C@]5(C)C4CCC3[C@@]2(C)CC1;
Subst1 = 2R,31-dihydroxy dotriacontanoic acid = SMILES C{31}C(O)CCCCCCCCCCCCCCCCCCCCCCCCCCCC{2}[C@@H](O){1}C(O)=O;
Subst2 = 25-hydroxy-hexacosanoic acid = SMILES C{25}C(O)CCCCCCCCCCCCCCCCCCCCCCC{1}C(O)=O |
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Structure type: oligomer
Trivial name: HoLA
Compound class: lipid A
- Compound ID: 14479
|
a-Kdop-(2-2)-a-D-Glcp-(1-4)-+
|
a-D-GlcpA-(1-3)-+ |
| |
3HOBut-(1-7)-b-Pse5Ac-(2-3)-3HOBut-(1-7)-b-Pse5Ac-(2-2)-b-D-GalpA-(1-4)-a-D-GalpA-(1-2)-b-D-GlcpA-(1-4)-a-D-GalpA-(1-3)-b-D-Glcp-(1-6)-a-D-Galp-(1-5)-a-Kdop |
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Structure type: oligomer
Compound class: core oligosaccharide, LPS
- Compound ID: 3770
|
3oxoMyr-(1-2)-+
|
3HODco-(1-3)-+ |
| |
C14={7}-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HODco-(1-3)-+ |
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Structure type: oligomer
Trivial name: pentaacyl monophosphoryl lipid A
Compound class: LPS, lipid A, glycolipid
Reference(s) to other database(s): CCSD:
48486, CBank-STR:9750
- Compound ID: 3969
|
-3)-R-3HOBut-(1-7)-b-Psep5Ac-(2-4)-a-D-FucpNAc-(1-3)-b-D-QuipNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 5484
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 9265
Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G25919EA
- Compound ID: 13145
|
R-3HOMyr-(1-3)-+
|
?%b-L-Arap4N-(1--P--1)--+ |
| |
?%b-L-Arap4N-(1--P--4)--+ | |
| | |
Myr-(1-3)-R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
R-3HOMyr-(1-3)-+ |
|
R-3HOPam-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 10622
|
b-L-ArapNAc3NAc4NAc-(1-4)-b-D-GlcpNAc3NAcA6NH2-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-4)-+
|
-3)-b-D-QuipNAc4NAc-(1-3)-a-D-Galp-(1-
AraN3N4N = 2,3,4-triamino-2,3,4-trideoxy-L-arabinose |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 12548
|
Pam-(1-3)-3HOMyr-(1-3)-+ 3HOMyr-(1-2)-+
| |
LIP25Ac-(1-3)-3HOMyr-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GalpA
| |
a-D-Manp-(1-4)-+ 3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 15682
|
a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+ a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
| | | |
a-L-Fucp-(1-2)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-{{{-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-}}}{{{-b-D-Galp-(1-4)-a-D-GlcpNAc-(1-3)-}}}b-D-Galp-(1-4)-a-D-GlcpNAc-(1-2)-D-gro-a-D-manHepp-(1-3)-{{{-D-gro-a-D-manHepp-(1-3)-}}}a-D-Glcp-(1-6)-{{{-a-D-Glcp-(1-6)-}}}/n=4/-D-gro-a-D-manHepp-(1-3)-a-L-Fucp-(1-3)-a-D-GlcpNAc-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdo-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
- Compound ID: 15684
|
3HOiMar-(1-2)-+
|
?%3HOPam-(1-3)-+ |
| |
iC15-(1-3)-3HOiMar-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
3HOPam-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 7740
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 15663
|
/Variants 0/-+
|
/Variants 1/-+ |
| |
a-D-GlcpNAc-(1-6)-+ | |
| | |
b-D-Galp-(1-6)-+ | | |
| | | |
a-D-Galp-(1-4)-a-D-Galp-(1-3)-a-D-Galp-(1-3)-a-D-Manp-(1-5)-a-Kdop
|
/Variants 2/-+
/Variants 0/ is:
P-4)-
OR (exclusively)
EtN-(1--P--4)--
/Variants 1/ is:
P-4)-
OR (exclusively)
EtN-(1--P--4)--
/Variants 2/ is:
P-2)-
OR (exclusively)
EtN-(1--P--2)-- |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 15665
|
a-D-GlcpN(%)Me-(1-7)-L-gro-a-D-manHepp-(1-3)-a-D-Manp4Me-(1-5)-a-Kdop-(2-4)-a-D-Manp-(1-4)-a-D-Glcp-(1-4)-a-Kdop |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 12365
|
b-D-Glcp-(1-6)-+
|
b-D-Quip1N4NAc-(1-6)-+ |
| |
-4)-a-D-GalpNAc-(1-3)-b-D-QuipNAc-(1-3)-a-D-GalpA-(1-4)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 13150
|
a-Kop-(2-6)-+
|
Pam-(1-3)-3HOMyr-(1-3)-+ | 3HOSte-(1-2)-+
| | |
Pam-(1-3)-3HOSte-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN-(1-1)-a-D-GlcpA
| |
a-D-Manp-(1-4)-+ 3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A