Found 70 structures.
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1. Compound ID: 1463
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R-3HOPam-(1-2)-+
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?%b-L-Arap4N-(1--P--1)--+ |
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?%b-L-Arap4N-(1--P--4)--+ | |
| | |
Myr-(1-3)-R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
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?%R-3HOMyr-(1-3)-+ |
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?%R-3HOMyr-(1-3)-+ |
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Structure type: oligomer
; 1933.1
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531,IEDB_176772
The structure is contained in the following publication(s):
- Article ID: 466
Silipo A, Molinaro A, Cescutti P, Bedini E, Rizzo R, Parrilli M, Lanzetta R "Complete structural characterization of the lipid A fraction of a clinical strain of B. cepacia genomovar I lipopolysaccharide" -
Glycobiology 15(5) (2005) 561-570
Burkholderia cepacia, a Gram negative bacterium ubiquitous in the environment, is a plant pathogen causing soft rot of onions. This microorganism has recently emerged as a life-threatening multiresistant pathogen in cystic fibrosis patients. An important virulence factor of B. cepacia is the lipopolysaccharide fraction. Clinical isolates and environmental strains possess LPS of high inflammatory nature which induces a high level production of cytokines. For the first time, the complete structure of the lipid A components isolated from the lipopolysaccharide fraction of a clinical strain of Burkholderia cepacia is herein described. The structural studies carried out by selective chemical degradations, mass spectrometry and NMR spectroscopy revealed multiple species differing in the acylation and in the phosphorylation patterns. The highest mass species was identified as a penta-acylated tetrasaccharide backbone containing two phosphoryl-arabinosamine residues in addition to the archetypal glucosamine disaccharide [Arap4N-L-β-1-P→4-β-D-GlcpN-(1→6)-α-D-GlcpN-1→P-1-β-L-Arap4N] . Lipid A fatty acids substitution was also described, with two 3-hydroxytetradecanoic acids 14:0 (3-OH) in ester linkage, and two 3-hydroxyhexadecanoic acids 16:0 (3-OH) in amide-linkage, one of which was substituted by a secondary a 14:0 residue at its C-3. Other lipid A species present in the mixture and exhibiting lower molecular weight lacked one or both β-L-Arap4N residues.
Lipopolysaccharide, LPS, Burkholderia, Burkholderia cepacia, lipid A, NMR spectroscopy, mass spectrometry
NCBI PubMed ID: 15610978Publication DOI: 10.1093/glycob/cwi029Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole Università degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, composition analysis, methanolysis
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2. Compound ID: 1464
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R-3HOPam-(1-2)-+
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b-L-Arap4N-(1--P--4)--+ |
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Myr-(1-3)-R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
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R-3HOMyr-(1-3)-+ P-1)-+ |
Show graphically |
Structure type: oligomer
; 1576.5
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531,IEDB_176772
The structure is contained in the following publication(s):
- Article ID: 466
Silipo A, Molinaro A, Cescutti P, Bedini E, Rizzo R, Parrilli M, Lanzetta R "Complete structural characterization of the lipid A fraction of a clinical strain of B. cepacia genomovar I lipopolysaccharide" -
Glycobiology 15(5) (2005) 561-570
Burkholderia cepacia, a Gram negative bacterium ubiquitous in the environment, is a plant pathogen causing soft rot of onions. This microorganism has recently emerged as a life-threatening multiresistant pathogen in cystic fibrosis patients. An important virulence factor of B. cepacia is the lipopolysaccharide fraction. Clinical isolates and environmental strains possess LPS of high inflammatory nature which induces a high level production of cytokines. For the first time, the complete structure of the lipid A components isolated from the lipopolysaccharide fraction of a clinical strain of Burkholderia cepacia is herein described. The structural studies carried out by selective chemical degradations, mass spectrometry and NMR spectroscopy revealed multiple species differing in the acylation and in the phosphorylation patterns. The highest mass species was identified as a penta-acylated tetrasaccharide backbone containing two phosphoryl-arabinosamine residues in addition to the archetypal glucosamine disaccharide [Arap4N-L-β-1-P→4-β-D-GlcpN-(1→6)-α-D-GlcpN-1→P-1-β-L-Arap4N] . Lipid A fatty acids substitution was also described, with two 3-hydroxytetradecanoic acids 14:0 (3-OH) in ester linkage, and two 3-hydroxyhexadecanoic acids 16:0 (3-OH) in amide-linkage, one of which was substituted by a secondary a 14:0 residue at its C-3. Other lipid A species present in the mixture and exhibiting lower molecular weight lacked one or both β-L-Arap4N residues.
Lipopolysaccharide, LPS, Burkholderia, Burkholderia cepacia, lipid A, NMR spectroscopy, mass spectrometry
NCBI PubMed ID: 15610978Publication DOI: 10.1093/glycob/cwi029Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy, Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole Università degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, SDS-PAGE, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, composition analysis, methanolysis
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3. Compound ID: 1465
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?%P-1)-+
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R-3HOPam-(1-2)-+ |
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3HOMyr-(1-3)-+ | |
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3HOBut-(1-27)-27HOMon-(1-3)-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
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P-4)-+ 3HOMyr-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 467
Silipo A, De Castro C, Lanzetta R, Molinaro A, Parrilli M "Full structural characterization of the lipid A components from the Agrobacterium tumefaciens strain C58 lipopolysaccharide fraction" -
Glycobiology 14(9) (2004) 805-815
For the first time, the complete structure of the lipid A from the lipopolysaccharide of an Agrobacterium species is here reported. In particular, the structure of the lipid A from A. tumefaciens strain C58, a soil pathogen bacterium strictly related to Rhizobiaceae, was determined. The structural study, carried out by chemical analysis, mass spectrometry, and nuclear magnetic resonance spectroscopy, revealed that lipid A fraction consisted of a mixture of species all sharing the bis-phosphorylated glucosamine disaccharide backbone that could be designated in two main structural motifs, according to the acylation pattern. The main species was a penta-acylated lipid A bearing two unsubstituted 14:0 (3-OH) fatty acids in ester linkage and two 16:0 (3-OH) in amide linkage; the one on GlcN II was O-acylated by a long chain fatty acid, 28:0 (27-OH). This in turn was esterified by a 3-hydroxy-butyroyl residue at its hydroxy group. The second species, in lesser amounts, was identified as a tetra-acylated lipid A and lacked the 14:0 (3-OH) residue on GlcN I. Other species deriving from these two lacked a phosphate group or 3-hydroxy-butyroyl residue or otherwise carried a 26:0 (25-OH) as long chain fatty acid. The lipid A structure of phytopathogen A. tumefaciens strain C58 presents deep structural analogies with lipid A of symbiotic Rhizobium, and the hypothesis is advanced that it can be a strategy of the bacterium to escape or attenuate the plant response
Lipopolysaccharide, lipid A, NMR spectroscopy, Agrobacterium tumefaciens, MALDI-TOF mass spectrometry
NCBI PubMed ID: 15159382Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia 4, 80126 Napoli, Italy
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, sugar analysis, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, methanolysis
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4. Compound ID: 1466
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R-3HOPam-(1-2)-+
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3HOMyr-(1-3)-+ |
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?%3HOBut-(1-27)-27HOMon-(1-3)-/Variants 0/-b-D-GlcpN-(1-6)-a-D-GlcpN
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P-4)-+
/Variants 0/ is:
3HOPam-(1-2)-
OR (exclusively)
LIP-(1-2)- |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 467
Silipo A, De Castro C, Lanzetta R, Molinaro A, Parrilli M "Full structural characterization of the lipid A components from the Agrobacterium tumefaciens strain C58 lipopolysaccharide fraction" -
Glycobiology 14(9) (2004) 805-815
For the first time, the complete structure of the lipid A from the lipopolysaccharide of an Agrobacterium species is here reported. In particular, the structure of the lipid A from A. tumefaciens strain C58, a soil pathogen bacterium strictly related to Rhizobiaceae, was determined. The structural study, carried out by chemical analysis, mass spectrometry, and nuclear magnetic resonance spectroscopy, revealed that lipid A fraction consisted of a mixture of species all sharing the bis-phosphorylated glucosamine disaccharide backbone that could be designated in two main structural motifs, according to the acylation pattern. The main species was a penta-acylated lipid A bearing two unsubstituted 14:0 (3-OH) fatty acids in ester linkage and two 16:0 (3-OH) in amide linkage; the one on GlcN II was O-acylated by a long chain fatty acid, 28:0 (27-OH). This in turn was esterified by a 3-hydroxy-butyroyl residue at its hydroxy group. The second species, in lesser amounts, was identified as a tetra-acylated lipid A and lacked the 14:0 (3-OH) residue on GlcN I. Other species deriving from these two lacked a phosphate group or 3-hydroxy-butyroyl residue or otherwise carried a 26:0 (25-OH) as long chain fatty acid. The lipid A structure of phytopathogen A. tumefaciens strain C58 presents deep structural analogies with lipid A of symbiotic Rhizobium, and the hypothesis is advanced that it can be a strategy of the bacterium to escape or attenuate the plant response
Lipopolysaccharide, lipid A, NMR spectroscopy, Agrobacterium tumefaciens, MALDI-TOF mass spectrometry
NCBI PubMed ID: 15159382Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cynthia 4, 80126 Napoli, Italy
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, HF solvolysis, sugar analysis, TLC, 31P NMR, MALDI-TOF MS, de-O-acylation with hydrazine, methanolysis
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5. Compound ID: 1639
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R-3HOPam-(1-2)-+
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/Variants 0/-+ |
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R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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P-4)-+ Pam-(1-3)-+
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
aiC15-(1-3)- |
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Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 509
Toman R, Garidel P, Andra J, Slaba K, Hussein A, Koch MH, Brandenburg K "Physicochemical characterization of the endotoxins from Coxiella burnetii strain Priscilla in relation to their bioactivities" -
BMC Biochemistry 5(1) (2004) 1
BACKGROUND: Coxiella burnetii is the etiological agent of Q fever found worldwide. The microorganism has like other Gram-negative bacteria a lipopolysaccharide (LPS, endotoxin) in its outer membrane, which is important for the pathogenicity of the bacteria. In order to understand the biological activity of LPS, a detailed physico-chemical analysis of LPS is of utmost importance. RESULTS: The lipid A moiety of LPS is tetraacylated and has longer (C-16) acyl chains than most other lipid A from enterobacterial strains. The two ester-linked 3-OH fatty acids found in the latter are lacking. The acyl chains of the C. burnetii endotoxins exhibit a broad melting range between 5 and 25 degrees C for LPS and 10 and 40 degrees C for lipid A. The lipid A moiety has a cubic inverted aggregate structure, and the inclination angle of the D-glucosamine disaccharide backbone plane of the lipid A part with respect to the membrane normal is around 40 degrees. Furthermore, the endotoxins readily intercalate into phospholipid liposomes mediated by the lipopolysaccharide-binding protein (LBP). The endotoxin-induced tumor necrosis factor alpha (TNF-α) production in human mononuclear cells is one order of magnitude lower than that found for endotoxins from enterobacterial strains, whereas the same activity as in the latter compounds is found in the clotting reaction of the Limulus amebocyte lysate assay. CONCLUSIONS: Despite a considerably different chemical primary structure of the C. burnetii lipid A in comparison with enterobacterial lipid A, the data can be well understood by applying the previously presented conformational concept of endotoxicity, a conical shape of the lipid A moiety of LPS and a sufficiently high inclination of the sugar backbone plane with respect to the membrane plane. Importantly, the role of the acyl chain fluidity in modulating endotoxicity now becomes more evident.
Lipopolysaccharide, X-ray diffraction, lipid A, endotoxin, Coxiella burnetii, lipopolysaccharide-binding, lipopolysaccharide-binding protein, liposome, Molecular Conformation, phospholipid, Matrix-Assisted Laser Desorption-Ionization
NCBI PubMed ID: 14715092Journal NLM ID: 101084098Publisher: London: BioMed Central
Correspondence: virutoma@savba.sk; kbranden@fz-borstel.de
Institutions: Institute of Virology, Slovak Academy of Sciences, Dubravska cesta 9, 84245 Bratislava, Slovak Republic, Martin-Luther-Universität Halle, Institut für Physikalische Chemie, Mühlpforte 1, 06108 Halle, Germany, Forschungszentrum Borstel, Div. of Biophysics, Parkallee 10, D-23845 Borstel, Germany, European Molecular Biology Laboratory, Hamburg outstation, EMBL c/o DESY, Notkestr. 85, D-22603 Hamburg
Methods: GC-MS, X-ray, SDS-PAGE, TLC, GC, MALDI-TOF MS, TNF-a assays, FTIR, composition analysis, UV, FRET
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6. Compound ID: 1819
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R-3HOPam-(1-2)-+
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R-3HOMyr-(1-3)-+ |
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Myr-(1-3)-R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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P-4)-+ |
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R-3HOMyr-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141807,IEDB_151531,IEDB_176772
The structure is contained in the following publication(s):
- Article ID: 573
Sforza S, Silipo A, Molinaro A, Marchelli R, Parrilli M, Lanzetta R "Determination of fatty acid positions in native lipid A by positive and negative electrospray ionization mass spectrometry" -
Journal of Mass Spectrometry 39(4) (2004) 378-383
Lipid A is the endotoxic principle of the lipopolysaccharide fraction from Gram-negative bacteria. It is involved in the elicitation of cytokine production that leads to massive inflammation and to septic shock as a lethal consequence. For this reason, the structural elucidation of lipopolysaccharides from toxic Gram-negative bacteria is an important and complicated task, mainly owing to its natural heterogeneity. Here, a new methodology to infer the distribution of the primary and secondary acyl residues is described, based on electrospray ionization mass spectrometry (ESI-MS) of intact lipid A under high cone voltage in order to achieve in-source fragmentation. Under these conditions, acyl fragmentation is induced and a different regioselective cleavage of secondary fatty acids is observed in positive and negative ESI-MS, allowing the rapid identification of the lipid A structure.
lipid A, Gram-negative bacteria, electrospray ionization mass spectrometry, fatty acid distribution, in-source collision-induced dissociation
NCBI PubMed ID: 15103651Journal NLM ID: 9504818Publisher: Chichester, UK: Wiley
Correspondence: lanzetta@unina.it
Institutions: Dipartimento di Chimica Organica e Industriale, Universita di Parma, Parco Area delle Scienze 17/a, I-43100 Parma, Italy, Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Complesso Universitario Monte Sant’Angelo, Via Cinthya 4, I-80126 Naples, Italy
Methods: ESI-MS, mild acid hydrolysis, CID-MS
- Article ID: 6082
Kawahara K "Variation, Modification and Engineering of Lipid A in Endotoxin of Gram-Negative Bacteria" -
International Journal of Molecular Sciences 22(5) (2021) 2281
Lipid A of Gram-negative bacteria is known to represent a central role for the immunological activity of endotoxin. Chemical structure and biosynthetic pathways as well as specific receptors on phagocytic cells had been clarified by the beginning of the 21st century. Although the lipid A of enterobacteria including Escherichia coli share a common structure, other Gram-negative bacteria belonging to various classes of the phylum Proteobacteria and other taxonomical groups show wide variety of lipid A structure with relatively decreased endotoxic activity compared to that of E. coli. The structural diversity is produced from the difference of chain length of 3-hydroxy fatty acids and non-hydroxy fatty acids linked to their hydroxyl groups. In some bacteria, glucosamine in the backbone is substituted by another amino sugar, or phosphate groups bound to the backbone are modified. The variation of structure is also introduced by the enzymes that can modify electrostatic charges or acylation profiles of lipid A during or after its synthesis. Furthermore, lipid A structure can be artificially modified or engineered by the disruption and introduction of biosynthetic genes especially those of acyltransferases. These technologies may produce novel vaccine adjuvants or antagonistic drugs derived from endotoxin in the future.
Lipopolysaccharide, lipid A, endotoxin, chemical structure, fatty acid, engineering
NCBI PubMed ID: 33668925Publication DOI: 10.3390/ijms22052281Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: kawahara@kanto-gakuin.ac.jp
Institutions: Department of Biosciences, College of Science and Engineering, Kanto Gakuin University, Yokohama, Kanagawa 236-8501, Japan
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7. Compound ID: 3795
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R-3HOiMar-(1-2)-+
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R-3HOPam-(1-3)-+ |
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iC15-(1-3)-R-3HOiMar-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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R-3HOiC15-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1447
Kato H, Haishima Y, Iida T, Tanaka A, Tanamoto K "Chemical structure of lipid A isolated from Flavobacterium meningosepticum lipopolysaccharide" -
Journal of Bacteriology 180(15) (1998) 3891-3899
The chemical structure of the lipid A of the lipopolysaccharide component isolated from Flavobacterium meningosepticum IFO 12535 was elucidated. Methylation and nuclear magnetic resonance analyses showed that two kinds of hydrophilic backbone exist in the free lipid A: a β(1→6)-linked 2-amino-2-deoxy-D-glucose, which is usually present in enterobacterial lipid A's, and a 2-amino-6-O-(2, 3-diamino-2,3-dideoxy-β-D-glucopyranosyl)-2-deoxy-D-glucose, in a molar ratio of 1.00:0.35. Both backbones were α-glycosidically phosphorylated in position 1, and the hydroxyl groups at positions 4, 4', and 6' were unsubstituted. Liquid secondary ion-mass spectrometry revealed a pseudomolecular ion at m/z 1673 [M-H]- as a major monophosphoryl lipid A component carrying five acyl groups. Fatty acid analysis showed that the lipid A contained 1 mol each of amide-linked (R)-3-OH iC17:0, ester-linked (R)-3-OH iC15:0, amide-linked (R)-3-O-(iC15:0)-iC17:0, and both amide- and ester-linked (R)-3-OH C16:0. Fatty acid distribution analyses using several mass spectrometry determinations demonstrated that the former two constituents were distributed on positions 2 and 3 of the reducing terminal unit of the backbones and that the latter two were attached to the 2' and 3' positions in the nonreducing terminal residue.
Lipopolysaccharide, structure, lipid, lipid A, chemical, chemical structure, Flavobacterium
NCBI PubMed ID: 9683486Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: tanamoto@nihs.go.jp
Institutions: Division of Microbiology, National Institute of Health Sciences, Setagayaku, Tokyo 158,1and, Department of Drug Analysis, Showa College of Pharmaceutical Sciences, Machida, Tokyo 194,2 Japan
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, de-O-acylation, 31P NMR, GLC, FAB-MS/MS, composition analysis, LSI-MS
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8. Compound ID: 3796
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R-3HOiMar-(1-2)-+
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R-3HOPam-(1-3)-+ |
| |
iC15-(1-3)-R-3HOiMar-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN-(1-P
|
R-3HOiC15-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1447
Kato H, Haishima Y, Iida T, Tanaka A, Tanamoto K "Chemical structure of lipid A isolated from Flavobacterium meningosepticum lipopolysaccharide" -
Journal of Bacteriology 180(15) (1998) 3891-3899
The chemical structure of the lipid A of the lipopolysaccharide component isolated from Flavobacterium meningosepticum IFO 12535 was elucidated. Methylation and nuclear magnetic resonance analyses showed that two kinds of hydrophilic backbone exist in the free lipid A: a β(1→6)-linked 2-amino-2-deoxy-D-glucose, which is usually present in enterobacterial lipid A's, and a 2-amino-6-O-(2, 3-diamino-2,3-dideoxy-β-D-glucopyranosyl)-2-deoxy-D-glucose, in a molar ratio of 1.00:0.35. Both backbones were α-glycosidically phosphorylated in position 1, and the hydroxyl groups at positions 4, 4', and 6' were unsubstituted. Liquid secondary ion-mass spectrometry revealed a pseudomolecular ion at m/z 1673 [M-H]- as a major monophosphoryl lipid A component carrying five acyl groups. Fatty acid analysis showed that the lipid A contained 1 mol each of amide-linked (R)-3-OH iC17:0, ester-linked (R)-3-OH iC15:0, amide-linked (R)-3-O-(iC15:0)-iC17:0, and both amide- and ester-linked (R)-3-OH C16:0. Fatty acid distribution analyses using several mass spectrometry determinations demonstrated that the former two constituents were distributed on positions 2 and 3 of the reducing terminal unit of the backbones and that the latter two were attached to the 2' and 3' positions in the nonreducing terminal residue.
Lipopolysaccharide, structure, lipid, lipid A, chemical, chemical structure, Flavobacterium
NCBI PubMed ID: 9683486Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: tanamoto@nihs.go.jp
Institutions: Division of Microbiology, National Institute of Health Sciences, Setagayaku, Tokyo 158,1and, Department of Drug Analysis, Showa College of Pharmaceutical Sciences, Machida, Tokyo 194,2 Japan
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, de-O-acylation, 31P NMR, GLC, FAB-MS/MS, composition analysis, LSI-MS
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9. Compound ID: 3986
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R-3HOMyr-(1-3)-+
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?%b-L-Arap4N-(1--P--1)--+ |
| |
?%R-3HOMyr-(1-3)-+ | |
| | |
Myr-(1-3)-R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
?%P-4)-+ |
|
R-3HOPam-(1-2)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531,IEDB_176772
The structure is contained in the following publication(s):
- Article ID: 1473
Molinaro A, Lindner B, De Castro C, Nolting B, Silipo A, Lanzetta R, Parrilli M, Holst O "The structure of lipid A of the lipopolysaccharide from Burkholderia caryophilli with a 4-amino-4-deoxy-L-arabinopyranose 1-phosphate residue exclusively in glycosidic linkage" -
Chemistry: a European Journal 9(7) (2003) 1542-1548
From the lipopolysaccharides (LPSs) of the plant-pathogenic bacterium Burkholderia caryophylli, the complete structure of lipid A has been characterized. For the first time, a 4-amino-4-deoxy-L-arabinopyranose 1-phosphate residue was proven to be exclusively linked to the reducing end of lipid A from a wild-type LPS. The LPSs of B. caryophylli were degraded by mild acetate buffer hydrolysis at pH 4.4. The obtained lipid A was analyzed as such, and also after de-O-acylation or dephosphorylation. The structure of lipid A was identified mainly by means of matrix-assisted laser desorption/ionisation mass spectrometry, and by various 1D and 2D (1)H and (13)C NMR spectroscopic measurements.
lipopolysaccharides, lipid A, NMR spectroscopy, mass spectrometry, Burkholderia caryophilli
NCBI PubMed ID: 12658652Publication DOI: 10.1002/chem.200390177Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: oholst@fz-borstel.de
Institutions: Divison of Structural Biochemistry, Research Center Borstel, Center for Medicine and Biosciences Parkallee 22, 23845 Borstel (Germany), Dipartimento di Chimica Organica e Biochimica, Università degli studi di Napoli Federico II, Italy
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, HF solvolysis, TLC, 31P NMR, GLC, chemical methods, MALDI-TOF MS, de-O-acetylation, NMR-1D
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10. Compound ID: 4001
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R-3HOSte-(1-2)-+
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Ste-(1-3)-R-3HOSte-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1--P--1)--EtN
|
R-3HOPam-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_141807,IEDB_151531,IEDB_534865
The structure is contained in the following publication(s):
- Article ID: 1486
Suda T, Kim Y, Ogawa T, Yasui N, Hasegawa Y, Kashihara W, Shimoyama T, Aoyama K, Nagata K, Tamura T, Kusumoto S "Chemical structure and biological activity of a lipid A component from Helicobacter pylori strain 206" -
Journal of Endotoxin Research 7(2) (2001) 95-104
The chemical structure of a lipid A, which was obtained as a minor component from lipopolysaccharide of Helicobacter pylori strain 206-1, was determined to be a glucosamine β-(1-6) disaccharide 1-(2-aminoethyl)phosphate acylated by (R)-3-hydroxyoctadecanoic acid, (R)-3- hydroxyhexadecanoic acid, and (R)-3-(octadecanoyloxy)octadecanoic acid at the 2-, 3- and 2'-positions, respectively. Compared with the other major lipid A from the same strain, which was previously reported [Suda Y, Ogawa T, Kashihara W et al. Chemical structure of lipid A from Helicobacter pylori strain 206-1 lipopolysaccharide. J Biochem 1997; 121: 1129--1133], the structure was very similar with one exception. An (R)-3-hydroxyhexadecanoic acid was present at the 3-position of the novel lipid A component. The structure is apparently identical to one of the proposals by Moran et al. [Moran AP, Lindner B, Walsh EJ. Structural characterization of the lipid A component of Helicobacter pylori rough- and smooth-form lipopolysaccharides. J Bacteriol 1997; 179: 6453--6463], who concluded the same structure as the so-called major lipid A from the H. pylori strain NCTC 11637 but without isolating a homogeneous component. The endotoxic properties and pro-inflammatory cytokine-inducing activities of this novel tetra-acyl type lipid A were lower than those of previously reported major tri-acyl type lipid A.
structure, lipid A, chemical structure, biological activity, Helicobacter pylori, Helicobacter
NCBI PubMed ID: 11521089Journal NLM ID: 9433350Publisher: Maney Publishing
Correspondence: ysuda@chem.sci.osaka-u.ac.jp
Institutions: Department of Chemistry, Graduate School of Science, Osaka University, Osaka, Japan, Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan, Department of Internal Medicine IV, Hyogo College of Medicine, Hyogo, Japan, Department of Bacteriology and Laboratory of Host Defenses, Institute for Advanced Medical Sciences (IAMS), Hyogo College of Medicine, Hyogo, Japan
Methods: 1H NMR, FAB-MS, SDS-PAGE, TLC, 31P NMR, ESI-MS, acid hydrolysis, ESI-MS/MS, GC, biological assays, composition analysis, LSI-MS, cytokine assay
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11. Compound ID: 4016
|
R-3HOPam-(1-3)-+
|
?%EtN-(1--P--1)--+ |
| |
Ste-(1-3)-R-3HOSte-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
|
R-3HOSte-(1-2)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_141807,IEDB_151531,IEDB_534865
The structure is contained in the following publication(s):
- Article ID: 1491
Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" -
Book: Endotoxin in Health and Disease (1999) 93-114
no abstract available
lipopolysaccharides, core, lipid A, O-polysaccharide, endotoxin, structural analysis, stucture
WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=falsePublisher: New York, Marcel Dekker, Inc.
Editors: Brade H, Opal SM, Vogel SN, Morrison DC
Institutions: Research Center Borstel, Borstel, Germany
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12. Compound ID: 4018
|
R-3HOPam-(1-3)-+
|
?%EtN-(1--P--1)--+ |
| |
Ste-(1-3)-R-3HOSte-(1-2)-+ | |
| | |
/Variants 0/-R-3HOPam-(1-3)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
?%P-4)-+ |
|
R-3HOSte-(1-2)-+
/Variants 0/ is:
Myr-(1-3)-
OR (exclusively)
Lau-(1-3)- |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864,IEDB_534865
The structure is contained in the following publication(s):
- Article ID: 1491
Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" -
Book: Endotoxin in Health and Disease (1999) 93-114
no abstract available
lipopolysaccharides, core, lipid A, O-polysaccharide, endotoxin, structural analysis, stucture
WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=falsePublisher: New York, Marcel Dekker, Inc.
Editors: Brade H, Opal SM, Vogel SN, Morrison DC
Institutions: Research Center Borstel, Borstel, Germany
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13. Compound ID: 4024
|
R-3HOPam-(1-2)-+
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Pam-(1-3)-R-3HOPam-(1-2)-+ |
| |
L-gro-a-D-manHepp-(1--P--4)--b-D-GlcpN-(1-6)-a-D-GlcpN-(1--P--1)--D-GalpA
| |
Lau-(1-3)-R-3HOMyr-(1-3)-+ |
|
R-3HOMyr-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531,IEDB_2189047,IEDB_534864
The structure is contained in the following publication(s):
- Article ID: 1491
Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" -
Book: Endotoxin in Health and Disease (1999) 93-114
no abstract available
lipopolysaccharides, core, lipid A, O-polysaccharide, endotoxin, structural analysis, stucture
WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=falsePublisher: New York, Marcel Dekker, Inc.
Editors: Brade H, Opal SM, Vogel SN, Morrison DC
Institutions: Research Center Borstel, Borstel, Germany
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14. Compound ID: 4037
|
R-3HOiMar-(1-2)-+
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R-3HOPam-(1-3)-+ |
| |
iC15-(1-3)-R-3HOiMar-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
R-3HOC15-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1491
Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" -
Book: Endotoxin in Health and Disease (1999) 93-114
no abstract available
lipopolysaccharides, core, lipid A, O-polysaccharide, endotoxin, structural analysis, stucture
WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=falsePublisher: New York, Marcel Dekker, Inc.
Editors: Brade H, Opal SM, Vogel SN, Morrison DC
Institutions: Research Center Borstel, Borstel, Germany
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15. Compound ID: 4038
|
R-3HOPam-(1-2)-+
|
R-3HOC15-(1-3)-+ |
| |
iC15-(1-3)-R-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
R-3HOPam-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1491
Zähringer U, Lindner B, Rietschel ET "Chemical structure of lipid A: recent advances in structural analysis of biologically active molecules" -
Book: Endotoxin in Health and Disease (1999) 93-114
no abstract available
lipopolysaccharides, core, lipid A, O-polysaccharide, endotoxin, structural analysis, stucture
WWW link: https://books.google.ru/books?id=oWhqhK1cE-gC&pg=PA93&lpg=PA93&dq=Chemical+structure+of+lipid+A:+recent+advances+in+structural+analysis+of+biologically+active+molecules&source=bl&ots=7h9_ecjijZ&sig=Pe0bcz2OlOZp_CZx135g91R0yHw&hl=ru&sa=X&ved=0ahUKEwiyr_j05pjNAhXICiwKHSptB2UQ6AEIGzAA#v=onepage&q=Chemical%20structure%20of%20lipid%20A%3A%20recent%20advances%20in%20structural%20analysis%20of%20biologically%20active%20molecules&f=falsePublisher: New York, Marcel Dekker, Inc.
Editors: Brade H, Opal SM, Vogel SN, Morrison DC
Institutions: Research Center Borstel, Borstel, Germany
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