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1. (Article ID: 3744)
Molinaro A, Newman M, Lanzetta R, Parrilli M
The structures of lipopolysaccharides from plant-associated Gram-negative bacteria
European Journal of Organic Chemistry 2009(34) (2009)
5887-5896
Gram-negative bacterial lipopolysaccharides (LPSs) have multiple roles in plant-microbe interactions. LPSs contribute to the low permeabilities of bacterial outer membranes, which act as barriers to protect bacteria from plant-derived antimicrobial substances. Conversely, perception of LPSs by plant cells can lead to the triggering of defence responses or to the priming of the plant to respond more rapidly and/or to a greater degree to subsequent pathogen challenge. LPSs are thus key molecules in the interactions between bacteria and plants, either in symbiosis or pathogenesis. Since LPSs are glycoconjugates genetically and chemically consisting of three different molecular regions, their detailed structure elucidation is a very topical and major scientific task for chemists, and is achieved by a combination of state-of-art chemical and spectroscopic techniques. Knowledge of LPSs' chemical structures is an important prerequisite for any further understanding of the biological processes in plant-microbe interactions. Moreover, the LPSs from Gram-negative bacteria - especially those originating from plant-associated bacteria - are a great source of novel monosaccharides with unusual and occasionally astounding chemical structures, never found in the eukaryotic world. This review presents the structures of LPSs from plant-associated bacteria isolated and identified from 2001 onwards.
lipopolysaccharides, structure elucidation, glycolipids, innate immunity, immunochemistry, plant-associated bacteria
Publication DOI: 10.1002/ejoc.200900682Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: molinaro

unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, via Cinthia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Faculty of Life Sciences, Department of Plant Biology & Biotechnology, University of Copenhagen, 1871 Frederiksberg, Denmark
The publication contains the following compound(s):
- Compound ID: 1427
|
-3)-a-L-FucpNAc-(1-3)-a-D-QuipNAc-(1-3)-a-L-FucpNAc-(1-2)-b-D-Quip3NAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G94472EZ, GlycomeDB:
27342
- Compound ID: 8605
|
b-D-GlcpNAc-(1-4)-+ a-Kdop-(2-4)-+
| |
a-L-Rhap-(1-3)-b-D-GlcpNAc-(1-3)-a-D-GalpNAc-(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:G79816DM, GlycomeDB:
27348
- Compound ID: 1445
Structure type: polymer chemical repeating unit
Trivial name: L-rhamnan, water-soluble EPS
Compound class: EPS, O-polysaccharide, O-antigen, polysaccharide, rhamnan
Reference(s) to other database(s): GTC:G60116ZJ, GlycomeDB:
27349
- Compound ID: 8585
|
b-GlcpNAc-(1-2)-+
|
-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G00785OL, GlycomeDB:
27530
- Compound ID: 8586
|
b-GlcpNAc-(1-2)-+
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G96793YB, GlycomeDB:
37383
- Compound ID: 1767
|
a-D-Galf-(1-2)-a-L-Rhap-(1-3)-b-D-Manp-(1-3)-a-L-Rhap-(1-3)-+
|
-4)-a-L-Rhap-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, EPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G84099GD, GlycomeDB:
27459
- Compound ID: 8592
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G21588FD, GlycomeDB:
37386
- Compound ID: 8603
|
a-L-Rhap-(1-6)-b-D-Glcp-(1-4)-+ P-6)-+ ?%EtN-(1---P---P---2)-+ a-Kdop-(2-4)-+
| | | |
b-D-GlcpNAc-(1-2)-a-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/
| |
Ala-(1-2)-+ P-4)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 8604
|
a-Kdop-(2-6)-b-D-Glcp-(1-4)-+ P-6)-+ ?%EtN-(1---P---P---2)-+ a-Kdop-(2-4)-+
| | | |
b-D-GlcpNAc-(1-2)-a-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/
| |
Ala-(1-2)-+ P-4)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 8601
|
L-Ala2Ac-(1-2)-+
|
-3)-b-D-QuipN4N-(1-3)-a-D-GlcpNAm-(1-3)-a-D-QuipNAc4NAc-(1-
|
L-Ala2Ac-(1-4)-+ |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 8596
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G40410TF
- Compound ID: 8588
|
a-L-Fucp3NAc-(1-3)-+
|
-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G72003MX
- Compound ID: 8590
|
a-L-Fucp3NAc-(1-3)-+
|
-2)-/Variants 0/-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-
/Variants 0/ is:
a-L-Rhap-(1-3)-
OR (exclusively)
a-L-Rhap-(1-2)- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 7729
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G47404WS, GlycomeDB:
36851
- Compound ID: 7782
|
b-D-Glcp-(1-3)-+
|
-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-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:G42224IR, GlycomeDB:
37390
- Compound ID: 8597
|
b-D-GlcpNAc-(1-4)-+
|
-4)-a-L-Rhap2Me-(1-3)-a-D-ManpN-(1-
|
S-3HOBut-(1-2)-+ |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 8598
|
D-Glcp-(1-2)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G88042PC, GlycomeDB:
37389
- Compound ID: 8595
|
/Variants 0/-+
|
-3)-a-L-6dTalp-(1-3)-b-D-GalpNAc-(1-
/Variants 0/ is:
?%b-D-Xylp-(1-4)-
OR (exclusively)
?%b-D-Xylp-(1-2)- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 1839
|
a-D-Fucp3NAc-(1-3)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: L-rhamnan
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G53459KL, GlycomeDB:
37252
- Compound ID: 3458
Structure type: polymer chemical repeating unit
Trivial name: O-antigen A-band
Compound class: O-polysaccharide, K-antigen, O-antigen
Reference(s) to other database(s): GTC:G22783IK, GlycomeDB:
5694
- Compound ID: 1652
Structure type: polymer chemical repeating unit
Trivial name: repeat unit of the lipopolysaccharide side-chain
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G16519OM, GlycomeDB:
27428
- Compound ID: 3269
|
a-D-Fucf-(1-4)-+
|
-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap3(65%)Me-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G42613RR
- Compound ID: 829
Structure type: polymer chemical repeating unit
Trivial name: common antigen, common polysaccharide antigen, A band polysaccharide, D-rhamnan, repeat unit of the lipopolysaccharide side-chain, A-band polysaccharide (A-PS), A-band polysaccharide
Compound class: O-polysaccharide, O-antigen, LPS, enterobacterial common antigen, CPA
Reference(s) to other database(s): GTC:G80135ZC, GlycomeDB:
25893
- Compound ID: 1701
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G45669LB, GlycomeDB:
27439
- Compound ID: 8591
|
?%a-D-Fucp3NAc-(1-2)-+
|
?%a-D-Fucp3NAc-(1-2)-+ |
| |
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G29553KF, GlycomeDB:
37385
- Compound ID: 8593
|
?%b-D-Xyl-(1-4)-+
|
?%b-D-Xyl-(1-4)-+ |
| |
?%b-D-Xyl-(1-4)-+ | |
| | |
-2)-a-L-Rhap-(1-2)-a-D-Glcp-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G25224QN
- Compound ID: 3270
|
a-D-Glcp-(1-3)-+
|
-3)-b-L-Rhap-(1-4)-a-L-Rhap-(1-3)-a-D-Fucp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G16936VX, GlycomeDB:
3470
- Compound ID: 4203
|
b-Erwiniose-(1-3)-a-D-Galp2Ac-(1-2)-+
|
-3)-a-D-Galp-(1-3)-a-D-Manp-(1-4)-a-L-Rhap-(1-
Erwiniose = 3,6,8-trideoxy-4-C-[(R)-1-hydroxyethyl)]-D-gulo-octose (erwiniose) |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 273
|
-2)-b-D-Rhap-(1-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: CPS, O-polysaccharide
Reference(s) to other database(s): GTC:G03470SB, GlycomeDB:
27764
- Compound ID: 4074
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-b-D-Manp-(1-4)-+
|
-3)-b-D-Galp-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G55556CH, GlycomeDB:
27611
- Compound ID: 8602
|
-4)-a-L-GulpNAcA3Ac6NH2-(1-3)-b-D-QuipNAc-(1-4)-a-L-GulpNAcA6NH2-(1-3)-b-D-QuipNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G55915DK, GlycomeDB:
37391
- Compound ID: 8606
|
a-D-GalpA-(1--P--4)--+
|
/Variants 0/-+ |
| |
?%a-D-Manp-(1-3)-?%a-D-Manp-(1-4)-b-D-Glcp-(1-4)-a-D-Manp-(1-5)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
P0NH2-(0-3)-
OR (exclusively)
a-D-GalpA-(1--P--3)-- |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
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