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1. (Article ID: 4766)
Korneev KV, Arbatsky NP, Molinaro A, Palmigiano A, Shaikhutdinova RZ, Shneider MM, Pier GB, Kondakova AN, Sviriaeva EN, Sturiale L, Garozzo D, Kruglov AA, Drutskaya MS, Nedospasov SA, Knirel YA, Kuprash DV
Contribution of the lipid A acyl groups to activation of murine Toll-Like Receptor 4 by lipopolysaccharides from various pathogenic strains of Gram-negative bacteria
Frontiers in Immunology 6 (2015)
595
Toll-like receptor 4 (TLR4) is required for activation of innate immunity upon recognition of lipopolysaccharide (LPS) of Gram-negative bacteria. The ability of TLR4 to respond to a particular LPS species is important since insufficient activation may not prevent bacterial growth while excessive immune reaction may lead to immunopathology associated with sepsis. Here we investigated the biological activity of LPS from Burkholderia mallei that causes glanders, and from the two well-known opportunistic pathogens Acinetobacter baumannii and Pseudomonas aeruginosa (causative agents of nosocomial infections). For each bacterial strain, R-form LPS was purified by hydrophobic chromatography and the chemical structure of lipid A, an LPS structural component, was elucidated by HR-MALDI-TOF mass spectrometry. The biological activity of LPS preparations was evaluated by their ability to induce production of proinflammatory cytokines, such as IL-6 and TNF, by bone marrow-derived macrophages (BMDM). Our results demonstrate direct correlation between the biological activity of LPS from these pathogenic bacteria and the extent of their lipid A acylation.
lipid A, Gram-negative bacteria, macrophages, innate immunity, acyl chains, proinflammatory cytokines
NCBI PubMed ID: 26635809Publication DOI: 10.3389/fimmu.2015.00595Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Kuprash DV
gmail.com>; Knirel YA gmail.com>
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia, Department of Chemical Sciences, Università di Napoli Federico II, Naples, Italy, CNR Institute for Polymers Composites and Biomaterials, Catania, Italy, State Centre of Applied Microbiology and Biotechnology, Obolensk, Moscow region, Russia, Shemyakin & Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Division of Infectious Diseases, Department of Medicine, Brigham and Women’s Hospital and Harvard Medical School, Boston, MA, USA, German Rheumatism Research Center (DRFZ), a Leibniz Institute, Berlin, Germany.
Methods: ELISA, MS/MS, biological assays, GPC, UV, RT-PCR, statistical analysis, HR-MALDI-TOF MS
The publication contains the following compound(s):
- Compound ID: 11947
|
3HOLau-(1-3)-3HOLau-(1-2)-+
|
P-4)-+ |
| |
3HOLau-(1-3)-3HOLau-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
|
P-1)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 11945
|
P-1)-+
|
Lau-(1-3)-3HOMyr-(1-2)-+ |
| |
P-4)-+ | |
| | |
a-Kdop-(2-4)-a-Kdop-(2-6)-+ | | |
| | | |
3HOLau-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
Lau-(1-3)-3HOLau-(1-3)-+ 3HOLau-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 11946
|
3HOMyr-(1-3)-+
|
?%b-L-Arap4N-(1--P--1)--+ |
| |
?%b-L-Arap4N-(1--P--4)--+ | |
| | |
3HOMyr-(1-3)-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
3HOMyr-(1-3)-+ 3HOPam-(1-2)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
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2. (Article ID: 4800)
Shashkov AS, Shneider MM, Senchenkova SN, Popova AV, Nikitina AS, Babenko VV, Kostryukova ES, Miroshnikov KA, Volozhantsev NV, Knirel YA
Structure of the capsular polysaccharide of Acinetobacter baumannii 1053 having the KL91 capsule biosynthesis gene locus
Carbohydrate Research 404 (2015)
79-82
Acinetobacter baumannii 1053 is the type strain for the maintenance of specific bacteriophage AP22, which infects a fairly broad range of A. baumannii strains circulating in Russian clinics and hospitals. A capsular polysaccharide (CPS) was isolated from cells of strain 1053 and studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the linear trisaccharide repeating unit was established: →4)-β-D-ManpNAcA-(1→4)-β-D-ManpNAcA-(1→3)-α-D-FucpNAc-(1→ where ManNAcA and FucNAc indicate 2-acetamido-2-deoxymannuronic acid and 2-acetamido-2,6-dideoxygalactose, respectively. A polysaccharide having the same repeating unit but a shorter chain was isolated by the phenol-water extraction of bacterial cells. Sequencing of the CPS biosynthesis gene locus showed that A. baumannii 1053 belongs to a new group designated KL91. The gene functions assigned putatively by a comparison with available databases were in agreement with the CPS structure established.
Acinetobacter baumannii, 2-acetamido-2, 6-dideoxy-D-galactose, capsular polysaccharide structure, 2-acetamido-2-deoxy-D-mannuronic acid, Polysaccharide biosynthesis gene locus
NCBI PubMed ID: 25665782Publication DOI: 10.1016/j.carres.2014.11.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Y.A. Knirel
gmail.com>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, M.M. Shemyakin & Y.A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Institute of Physical-Chemical Medicine, Moscow, Russia, Institute of Fundamental Medicine and Biology, Kazan (Volga Region) Federal University, Kazan, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, DNA sequencing, sugar analysis, acid hydrolysis, GLC, mild acid hydrolysis, NMR-1D, GPC, extraction, bioinformatic analysis
The publication contains the following compound(s):
- Compound ID: 12026
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G52976SY
- Compound ID: 12027
Structure type: fragment of a bigger structure
Trivial name: polysaccharide (PS)
Reference(s) to other database(s): GTC:G93871SB
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3. (Article ID: 4819)
Giguere D
Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses
Carbohydrate Research 418 (2015)
29-43
The emergence of multidrug-resistance Acinetobacter baumannii requires novel approaches for prevention, treatment and diagnosis. The structures of surface polysaccharides from A. baumannii are valuable tools to understand pathogenesis, virulence and immunogenicity. The synthesis of bacterial mono- or polysaccharides may result in novel probes to become important therapeutic options in the fight against A. baumannii. This report exemplifies the relevance of glycochemistry for the development of new antibiotics.
lipopolysaccharides, capsular polysaccharides, Acinetobacter, Acinetobacter baumannii, polysaccharide synthesis, surface polysaccharides
NCBI PubMed ID: 26531136Publication DOI: 10.1016/j.carres.2015.10.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: denis.giguere

chm.ulaval.ca
Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
The publication contains the following compound(s):
- Compound ID: 12079
Structure type: homopolymer
; n=9
Aglycon: 3-(4-(acetylthio)butyrylamino)propyl or spacer + carrier protein (Tetanus Toxoid)
Trivial name: PNAG
Reference(s) to other database(s): GTC:G11006VI
- Compound ID: 327
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G70774JU, GlycomeDB:
25556
- Compound ID: 328
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, LPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G52429QS, GlycomeDB:
6694
- Compound ID: 728
|
a-L-FucpNAc-(1-4)-+
|
-3)-a-D-GalpNAcA-(1-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G73635WZ, GlycomeDB:
25208
- Compound ID: 12077
|
a-Kdop-(2-4)-+
|
b-D-GlcpN-(1-7)-+ |
| |
a-D-GalpN(%)Ac-(1-4)-+ | |
| | |
a-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-a-D-GlcpNAcA-(1-4)-a-Kdop-(2-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G80033MB
- Compound ID: 12078
|
a-Kdop-(2-4)-+
|
b-D-GlcpN-(1-7)-+ |
| |
a-D-GalpN(%)Ac-(1-4)-a-D-GlcpNAcA-(1-4)-a-Kdop-(2-5)-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:G20251VZ
- Compound ID: 12072
|
/Variants 0/-+
|
-4)-a-D-GlcpNAc6(50%)Ac-(1-4)-a-D-GalpNAcA-(1-3)-b-D-QuipNAc4N-(1-
/Variants 0/ is:
66%Ac-4)-
OR (exclusively)
33%R-3HOBut-(1-4)- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
- Compound ID: 2076
|
b-D-ManpNAc-(1-4)-a-D-Galp-(1-4)-+
|
-3)-b-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G40148IO, GlycomeDB:
25205
- Compound ID: 12080
Structure type: oligomer
Trivial name: repeating unit of the O-polysaccharide
Reference(s) to other database(s): GTC:G50329IW
- Compound ID: 2077
|
b-D-Glcp-(1-6)-+
|
-4)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-6)-b-D-Galp-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G69238MT, GlycomeDB:
25206
- Compound ID: 2078
|
b-D-Glcp-(1-3)-+
|
-6)-a-D-GlcpNAc-(1-4)-a-D-GalpNAc-(1-3)-a-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: surface polysaccharide
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G53088UD, GlycomeDB:
25207
- Compound ID: 2085
|
/Variants 0/-+
|
-6)-a-D-GlcpNAc-(1-3)-a-L-FucpNAc-(1-3)-a-D-GlcpNAc-(1-4)-b-Legp7Ac-(2-
/Variants 0/ is:
50%S-3HOBut-(1-5)-
OR (exclusively)
50%Ac-5)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
- Compound ID: 2087
|
R-3HOBut-(1-3)-b-D-Quip3N-(1-6)-a-D-GlcpNAc-(1-4)-+
|
-3)-b-D-GlcpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
- Compound ID: 2088
|
a-D-Glcp-(1-6)-+
|
-3)-b-D-Quip4NAc-(1-3)-a-D-GalpNAc-(1-4)-a-D-GalpNAc-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: type K57 CPS
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G82786KR, GlycomeDB:
25210, SpecDB: ol.9
- Compound ID: 2089
|
b-L-Rhap-(1-4)-b-D-GlcpNAc-(1-3)-+
|
-3)-a-D-GlcpNAc-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G32499RM, GlycomeDB:
25211
- Compound ID: 5483
|
a-D-ManpNAc-(1-3)-+
|
-3)-a-D-GlcpNAc-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G94329VK, GlycomeDB:
6779
- Compound ID: 8566
|
b-D-GlcpNAc3NAcA-(1-4)-+
|
-6)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-
|
b-D-GlcpNAc-(1-6)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G47927SM, GlycomeDB:
37288
- Compound ID: 11322
|
b-D-GlcpNAc3NAcA4Ac-(1-4)-+
|
-3)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-
|
b-D-GlcpNAc-(1-6)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: O-glycan
Compound class: CPS
Reference(s) to other database(s): GTC:G64997NS
- Compound ID: 12073
|
/Variants 0/-+
|
-4)-a-D-GlcpNAc6(50%)Ac-(1-4)-a-L-GalpNAcA-(1-3)-b-D-QuipNAc4N-(1-
/Variants 0/ is:
66%Ac-4)-
OR (exclusively)
33%R-3HOBut-(1-4)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 10877
|
a-Kdop-(2-4)-+
|
b-D-GlcpN-(1-7)-+ |
| |
a-D-GalpN-(1-4)-+ | |
| | |
a-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-a-D-GlcpNAcA-(1-4)-a-Kdop-(2-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LOS
Reference(s) to other database(s): GTC:G87252TX
- Compound ID: 12076
|
a-Kdop-(2-4)-+
|
a-D-GlcpNAc-(1-4)-b-D-GlcpNA-(1-4)-+ |
| |
?%a-L-Rhap-(1-3)-?%a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-8)-a-Kdop-(2-5)-a-Kdop-(2-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G08271SD
- Compound ID: 11621
|
a-Psep5Ac7Ac-(2-6)-b-D-Glcp-(1-6)-+
|
-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, polysaccharide
Reference(s) to other database(s): GTC:G97931NE, GenDB:JX976549.1
- Compound ID: 11852
Structure type: polymer chemical repeating unit
Compound class: CPS, cell wall polysaccharide
Reference(s) to other database(s): GTC:G73006WP
- Compound ID: 11899
|
b-D-Glcp-(1-6)-+
|
-4)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G71656OE
- Compound ID: 12074
|
-4)-a-Psep5Ac7Ac-(2-6)-b-D-Galp-(1-6)-b-D-Galp-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G91504ME
- Compound ID: 12026
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G52976SY
- Compound ID: 12014
|
R-3HOBut-(1-7)-a-Psep5Ac-(2-4)-+
|
-3)-b-D-Ribp-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 12013
|
/Variants 0/-+
|
-3)-b-D-ManpNAcA-(1-4)-b-D-ManpNAcA-(1-3)-a-D-QuipNAc4N-(1-
/Variants 0/ is:
71%S-3HOBut-(1-4)-
OR (exclusively)
29%Ac-4)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
- Compound ID: 12028
|
b-D-Glcp-(1-3)-+
|
-2)-a-D-Galp-(1-6)-a-D-Glcp-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G68883RH
- Compound ID: 12029
|
b-D-Glcp-(1-3)-+
|
-3)-a-D-Glcp-(1-6)-a-D-GlcpNAc-(1-4)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G35428RP
- Compound ID: 12031
|
b-D-Glcp-(1-3)-+
|
-4)-a-D-GalpNAc6(50%)Ac-(1-4)-a-D-GalpNAc-(1-3)-a-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G57327XB
- Compound ID: 12075
|
a-Acip5Ac7Ac-(2-6)-+
|
-3)-a-D-GalpNAc-(1-3)-a-L-FucpNAc-(1-3)-a-D-FucpNAc-(1-
Aci = 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-altro-non-2-ulosonic (acinetaminic) acid (5,7-di-N-acetyl-acinetaminic acid Aci5Ac7Ac) |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Reference(s) to other database(s): GTC:G90675WE
- Compound ID: 1030
Structure type: homopolymer
Trivial name: poly-β-1,6-GlcNAc (PGA), biofilm, poly-b-(1-6)-N-acetyl-D-glucosamine (PNAG), poly-β-N-acetyl-glucosamine (PNAG), PNAG, poly-N-acetylglucosamine, PNAG
Compound class: CPS, EPS, O-polysaccharide, glucan, polysaccharide
Reference(s) to other database(s): GTC:G36952FI, GlycomeDB:
11210
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