Found 49 structures.
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1. Compound ID: 14
a-D-Glcp-(1-3)-+
|
a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-+
|
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: lipooligosaccharide core L2
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_418762,IEDB_418764,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 7
Berrington AW, Tan YC, Srikhanta Y, Kuipers B, van der LP, Peak IR, Jennings MP "Phase variation in meningococcal lipooligosaccharide biosynthesis genes" -
FEMS Immunology and Medical Microbiology 34(4) (2002) 267-275
Neisseria meningitidis expresses a range of lipooligosaccharide (LOS) structures, comprising of at least 13 immunotypes (ITs). Meningococcal LOS is subject to phase variation of its terminal structures allowing switching between ITs, which is proposed to have functional significance in disease. The objectives of this study were to investigate the repertoire of structures that can be expressed in clinical isolates, and to examine the role of phase-variable expression of LOS genes during invasive disease. Southern blotting was used to detect the presence of LOS biosynthetic genes in two collections of meningococci, a global set of strains previously assigned to lineages of greater or lesser virulence, and a collection of local clinical isolates which included paired throat and blood isolates from individual patients. Where the phase-variable genes lgtA, lgtC or lgtG were identified, they were amplified by PCR and the homopolymeric tracts, responsible for their phase-variable expression, were sequenced. The results revealed great potential for variation between alternate LOS structures in the isolates studied, with most strains capable of expressing several alternative terminal structures. The structures predicted to be currently expressed by the genotype of the strains agreed well with conventional immunotyping. No correlation was observed between the structural repertoire and virulence of the isolate. Based on the potential for LOS phase variation in the clinical collection and observations with the paired patient isolates, our data suggest that phase variation of LOS structures is not required for translocation between distinct compartments in the host
Lipopolysaccharide, biosynthesis, structure, Meningococcus, Phase variation, Lipooligosaccharide, Pathogenesis, Neisseria meningitidis, alternative, Bacterial Proteins, biosynthetic, blood, blotting, chemistry, clinical, correlation, disease, expression, functional, gene, Gene Expression Regulation, Bacterial, genetics, genotype, growth & development, host, human, immunotype, immunotyping, invasive, isolate, LOS, meningococcal, Meningococcal Infections, meningococci, metabolism, microbiology, Neisseria, pathogenicity, PCR, phase, phenotype, polymerase chain reaction, potential, role, Sequence Analysis, DNA, significance, strain, structural, Support, Non-U.S.Gov't, terminal, tract, translocation, variation, Variation (Genetics), virulence
NCBI PubMed ID: 12443826Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: jennings@biosci.uq.edu.au
Institutions: Department of Microbiology and Parasitology, University of Queensland, St. Lucia, Brisbane, Qld 4072, Australia, National Institute of Public Health and the Environment, Bilthoven, The Netherlands, School of Health Science, Gri?th University, Gold Coast Campus, Qld 4217, Australia
Methods: PCR, DNA sequencing
- Article ID: 277
Kahler CM, Carlson RW, Rahman MM, Martin LE, Stephens DS "Two glycosyltransferase genes, lgtF and rfaK, constitute the lipooligosaccharide ice (inner core extension) biosynthesis operon of Neisseria meningitidis" -
Journal of Bacteriology 178(23) (1996) 6677-6684
We have characterized an operon required for inner-core biosynthesis of the lipooligosaccharide (LOS) of Neisseria meningitidis. Using Tn916 mutagenesis, we recently identified the α-1,2-N-acetylglucosamine (GlcNAc) transferase gene (rfaK), which when inactivated prevents the addition of GlcNAc and alpha chain to the meningococcal LOS inner core (C. M. Kahler, R. W. Carlson, M. M. Rahman, L. E. Martin, and D. S. Stephens, J. Bacteriol. 178:1265-1273, 1996). During the study of rfaK, a second open reading frame (lgtF) of 720 bp was found upstream of rfaK. An amino acid sequence homology search of the GenBank and EMBL databases revealed that the amino terminus of LgtF has significant homology with a family of β-glycosyltransferases involved in the biosynthesis of polysaccharides and O antigen of lipopolysaccharides. The chromosomal copy of lgtF was mutagenized with a nonpolar antibiotic resistance cassette to minimize potential polar effects on rfaK. Tricine sodium dodecyl sulfate-polyacrylamide gel electrophoresis and composition analysis of the LOS from the nonpolar lgtF mutant showed that this strain produced a truncated LOS structure which contained a LOS inner core of GlcNAc1Hep2KDO2lipid A but without the addition of lacto-N-neotetraose to HepI or glucose to HepII. These results and the amino acid homology with β-glycosyltransferases suggest that lgtF encodes the UDP-glucose:LOS-β-1,4-glucosyltransferase which attaches the first glucose residue to HepI of LOS. Reverse transcriptase PCR and primer extension analysis indicate that both lgtF and rfaK are cotranscribed as a polycistronic message from a promoter upstream of lgtF. This arrangement suggests that completion of the LOS inner core and the initiation of the alpha chain addition are tightly coregulated in N. meningitidis.
biosynthesis, Lipooligosaccharide, Neisseria meningitidis, gene, inner core, glycosyltransferase, operon
NCBI PubMed ID: 8955282Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: dstep01@emory.edu
Institutions: Departments of Medicine and Microbiology and Immunology, Emory University School of Medicine and Department of Veterans Affairs Medical Center, Atlanta, and The Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia
Methods: genetic methods
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2. Compound ID: 362
a-D-Glcp-(1-3)-+ b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+
| | |
a-D-GlcpNAc-(1-2)-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: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 107
Tong YH, Reinhold V, Reinhold B, Brandt B, Stein DC "Structural and immunochemical characterization of the lipooligosaccharides expressed by Neisseria subflava 44" -
Journal of Bacteriology 183(3) (2001) 942-950
Neisserial lipooligosaccharides (LOSs) are a family of complex cell surface glycolipids. We used mass spectrometry techniques (electrospray ionization, collision-induced dissociation, and multiple step), combined with fluorophore-assisted carbohydrate electrophoresis monosaccharide composition analysis, to determine the structure of the two low-molecular-mass LOS molecules (LOSI and LOSII) expressed by Neisseria subflava 44. We determined that LOSI contains one glucose on both the alpha and beta chains. LOSII is structurally related to LOSI and differs from it by the addition of a hexose (either glucose or galactose) on the alpha chain. LOSI and LOSII were able to bind monoclonal antibody (MAb) 25-1-LC1 when analyzed by Western blotting experiments. We used a set of genetically defined Neisseria gonorrhoeae mutants that expressed single defined LOS epitopes and a group of Neisseria meningitidis strains that expresses chemically defined LOS components to determine the structures recognized by MAb 25-1-LC1. We found that extensions onto the beta-chain glucose of LOSI block the recognition by this MAb, as does further elongation from the LOSII alpha chain. The LOSI structure was determined to be the minimum structure that is recognized by MAb 25-1-LC1.
Lipooligosaccharide, Neisseria, structural, characterization, immunochemical, lipooligosaccharides
NCBI PubMed ID: 11208793Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: DS64@UMAIL.UMD.EDTJ
Institutions: Department of Cell Biology and Molecular Genetics, University of Maryland, College Park, Maryland 20742
Methods: ESI-MS, CID-MS/MS, FACE
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3. Compound ID: 382
a-D-GlcpNAc-(1-2)-+
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/Variants 0/-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/
/Variants 0/ is:
EtN-(1--P--3)--
OR (exclusively)
a-D-Glcp-(1-3)- |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130659,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_175430,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418761,IEDB_418762,IEDB_418763,IEDB_418764,IEDB_418765,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_419430,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 121
Tsai CM, Kao G, Zhu P "Influence of the length of the lipooligosaccharide a chain on its sialylation in Neisseria meningitidis" -
Infection and Immunity 70(1) (2002) 407-411
The sialylation of lipooligosaccharide (LOS) in Neisseria meningitidis plays a role in the resistance of the organism to killing by normal human serum. The length of the alpha chain extending out from the heptose I [Hep (I)] moiety of LOS influenced sialylation of N. meningitidis LOS in vitro and in vivo. The alpha chain required a terminal Gal and a trisaccharide or longer oligosaccharide to serve as an acceptor for sialylation. The disaccharide lactose (Galβ1-4Glc) in the alpha chain of immunotype L8 LOS could not function as an acceptor for the sialyltransferase, probably due to steric hindrance imposed by the neighboring Hep (II) with phosphorylethanolamine and another group attached.
Lipooligosaccharide, Neisseria meningitidis, sialyltransferase, structure-activity relationship, Substrate Specificity
NCBI PubMed ID: 11748209Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: tsai@cber.fda.gov
Institutions: Division of Bacterial, Parasitic, and Allergenic Products, Center for Biologics, Food and Drug Administration, Bethesda, MD, USA
Methods: SDS-PAGE
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4. Compound ID: 511
a-D-GlcpNAc-(1-2)-+
|
/Variants 0/-L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
| |
?%a-Neup5Ac-(2-3)-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/
/Variants 0/ is:
EtN-(1--P--3)--
OR (exclusively)
a-D-Glcp-(1-3)- |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_175430,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418765,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_419430,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_170,SB_171,SB_172,SB_178,SB_187,SB_192,SB_195,SB_31,SB_39,SB_6,SB_62,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 121
Tsai CM, Kao G, Zhu P "Influence of the length of the lipooligosaccharide a chain on its sialylation in Neisseria meningitidis" -
Infection and Immunity 70(1) (2002) 407-411
The sialylation of lipooligosaccharide (LOS) in Neisseria meningitidis plays a role in the resistance of the organism to killing by normal human serum. The length of the alpha chain extending out from the heptose I [Hep (I)] moiety of LOS influenced sialylation of N. meningitidis LOS in vitro and in vivo. The alpha chain required a terminal Gal and a trisaccharide or longer oligosaccharide to serve as an acceptor for sialylation. The disaccharide lactose (Galβ1-4Glc) in the alpha chain of immunotype L8 LOS could not function as an acceptor for the sialyltransferase, probably due to steric hindrance imposed by the neighboring Hep (II) with phosphorylethanolamine and another group attached.
Lipooligosaccharide, Neisseria meningitidis, sialyltransferase, structure-activity relationship, Substrate Specificity
NCBI PubMed ID: 11748209Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: tsai@cber.fda.gov
Institutions: Division of Bacterial, Parasitic, and Allergenic Products, Center for Biologics, Food and Drug Administration, Bethesda, MD, USA
Methods: SDS-PAGE
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5. Compound ID: 512
a-D-GlcpNAc-(1-2)-+
|
/Variants 0/-L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
| |
?%a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-Glcp-(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--3)--
OR (exclusively)
a-D-Glcp-(1-3)- |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_130679,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_175430,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_419430,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_37,SB_39,SB_6,SB_68,SB_7,SB_76,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 121
Tsai CM, Kao G, Zhu P "Influence of the length of the lipooligosaccharide a chain on its sialylation in Neisseria meningitidis" -
Infection and Immunity 70(1) (2002) 407-411
The sialylation of lipooligosaccharide (LOS) in Neisseria meningitidis plays a role in the resistance of the organism to killing by normal human serum. The length of the alpha chain extending out from the heptose I [Hep (I)] moiety of LOS influenced sialylation of N. meningitidis LOS in vitro and in vivo. The alpha chain required a terminal Gal and a trisaccharide or longer oligosaccharide to serve as an acceptor for sialylation. The disaccharide lactose (Galβ1-4Glc) in the alpha chain of immunotype L8 LOS could not function as an acceptor for the sialyltransferase, probably due to steric hindrance imposed by the neighboring Hep (II) with phosphorylethanolamine and another group attached.
Lipooligosaccharide, Neisseria meningitidis, sialyltransferase, structure-activity relationship, Substrate Specificity
NCBI PubMed ID: 11748209Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: tsai@cber.fda.gov
Institutions: Division of Bacterial, Parasitic, and Allergenic Products, Center for Biologics, Food and Drug Administration, Bethesda, MD, USA
Methods: SDS-PAGE
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6. Compound ID: 513
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/
/Variants 0/ is:
EtN-(1--P--3)--
OR (exclusively)
a-D-Glcp-(1-3)- |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_136044,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_175430,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418765,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_419430,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 121
Tsai CM, Kao G, Zhu P "Influence of the length of the lipooligosaccharide a chain on its sialylation in Neisseria meningitidis" -
Infection and Immunity 70(1) (2002) 407-411
The sialylation of lipooligosaccharide (LOS) in Neisseria meningitidis plays a role in the resistance of the organism to killing by normal human serum. The length of the alpha chain extending out from the heptose I [Hep (I)] moiety of LOS influenced sialylation of N. meningitidis LOS in vitro and in vivo. The alpha chain required a terminal Gal and a trisaccharide or longer oligosaccharide to serve as an acceptor for sialylation. The disaccharide lactose (Galβ1-4Glc) in the alpha chain of immunotype L8 LOS could not function as an acceptor for the sialyltransferase, probably due to steric hindrance imposed by the neighboring Hep (II) with phosphorylethanolamine and another group attached.
Lipooligosaccharide, Neisseria meningitidis, sialyltransferase, structure-activity relationship, Substrate Specificity
NCBI PubMed ID: 11748209Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: tsai@cber.fda.gov
Institutions: Division of Bacterial, Parasitic, and Allergenic Products, Center for Biologics, Food and Drug Administration, Bethesda, MD, USA
Methods: SDS-PAGE
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7. Compound ID: 524
b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
|
a-D-Glcp-(1-3)-+ | a-Kdop-(2-4)-+
| | |
a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_136044,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 107
Tong YH, Reinhold V, Reinhold B, Brandt B, Stein DC "Structural and immunochemical characterization of the lipooligosaccharides expressed by Neisseria subflava 44" -
Journal of Bacteriology 183(3) (2001) 942-950
Neisserial lipooligosaccharides (LOSs) are a family of complex cell surface glycolipids. We used mass spectrometry techniques (electrospray ionization, collision-induced dissociation, and multiple step), combined with fluorophore-assisted carbohydrate electrophoresis monosaccharide composition analysis, to determine the structure of the two low-molecular-mass LOS molecules (LOSI and LOSII) expressed by Neisseria subflava 44. We determined that LOSI contains one glucose on both the alpha and beta chains. LOSII is structurally related to LOSI and differs from it by the addition of a hexose (either glucose or galactose) on the alpha chain. LOSI and LOSII were able to bind monoclonal antibody (MAb) 25-1-LC1 when analyzed by Western blotting experiments. We used a set of genetically defined Neisseria gonorrhoeae mutants that expressed single defined LOS epitopes and a group of Neisseria meningitidis strains that expresses chemically defined LOS components to determine the structures recognized by MAb 25-1-LC1. We found that extensions onto the beta-chain glucose of LOSI block the recognition by this MAb, as does further elongation from the LOSII alpha chain. The LOSI structure was determined to be the minimum structure that is recognized by MAb 25-1-LC1.
Lipooligosaccharide, Neisseria, structural, characterization, immunochemical, lipooligosaccharides
NCBI PubMed ID: 11208793Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: DS64@UMAIL.UMD.EDTJ
Institutions: Department of Cell Biology and Molecular Genetics, University of Maryland, College Park, Maryland 20742
Methods: ESI-MS, CID-MS/MS, FACE
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8. Compound ID: 525
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
a-D-Glcp-(1-3)-+ | a-Kdop-(2-4)-+
| | |
a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 107
Tong YH, Reinhold V, Reinhold B, Brandt B, Stein DC "Structural and immunochemical characterization of the lipooligosaccharides expressed by Neisseria subflava 44" -
Journal of Bacteriology 183(3) (2001) 942-950
Neisserial lipooligosaccharides (LOSs) are a family of complex cell surface glycolipids. We used mass spectrometry techniques (electrospray ionization, collision-induced dissociation, and multiple step), combined with fluorophore-assisted carbohydrate electrophoresis monosaccharide composition analysis, to determine the structure of the two low-molecular-mass LOS molecules (LOSI and LOSII) expressed by Neisseria subflava 44. We determined that LOSI contains one glucose on both the alpha and beta chains. LOSII is structurally related to LOSI and differs from it by the addition of a hexose (either glucose or galactose) on the alpha chain. LOSI and LOSII were able to bind monoclonal antibody (MAb) 25-1-LC1 when analyzed by Western blotting experiments. We used a set of genetically defined Neisseria gonorrhoeae mutants that expressed single defined LOS epitopes and a group of Neisseria meningitidis strains that expresses chemically defined LOS components to determine the structures recognized by MAb 25-1-LC1. We found that extensions onto the beta-chain glucose of LOSI block the recognition by this MAb, as does further elongation from the LOSII alpha chain. The LOSI structure was determined to be the minimum structure that is recognized by MAb 25-1-LC1.
Lipooligosaccharide, Neisseria, structural, characterization, immunochemical, lipooligosaccharides
NCBI PubMed ID: 11208793Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: DS64@UMAIL.UMD.EDTJ
Institutions: Department of Cell Biology and Molecular Genetics, University of Maryland, College Park, Maryland 20742
Methods: ESI-MS, CID-MS/MS, FACE
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9. Compound ID: 529
a-D-GlcpNAc-(1-2)-+
|
EtN-(1--P--7)--L-gro-a-D-manHepp-(1-3)-+
| |
a-D-Glcp-(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/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130659,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418762,IEDB_418764,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 120
Tsai C, Chen WH, Balakonis PA "Characterization of terminal NeuNAca2-3Galb1-4GlcNAc sequence in lipooligosaccharide of Neisseria meningitidis" -
Glycobiology 8(4) (1998) 359-365
Group B and C Neisseria meningitidis are the major cause of meningococcal disease in the United States and in Europe. N . meningitidis lipooligosaccharide (LOS), a major surface antigen, can be divided into 12 immunotypes of which L1 through L8 were found among Group B and C organisms. Groups B and C but not Group A may sialylate their LOSs with N-acetylneuraminic acid (NeuNAc) at the nonreducing end because they synthesize CMP-NeuNAc. Using sialic acid-galactose binding lectins as probes in an ELISA format, six of the eight LOS immunotypes (L2, L3, L4, L5, L7, and L8) in Groups B and C bound specifically to Maackia amurensis leukoagglutinin (MAL), which recognizes NeuNAcα2-3Galβ1-4GlcNAc/Glc sequence, but not to Sambucus nigra agglutinin, which binds NeuNAcα2-6Gal sequence. The combination of SDS-PAGE and MAL-blot analyses revealed that these six LOSs contained only the NeuNAcα2-3Galβ1-4GlcNAc trisaccharide sequence in their 4.1 kDa LOS components, which have a common terminal lacto-N-neotetraose (LNnT, Galβ1-4GlcNAcβ1-3Galβ1-4Glc) structure when nonsialylated as shown by previous studies. The LOS-lectin binding was abolished when the LOSs were treated with Newcastle disease viral neuraminidase which cleaves α2→3 linked sialic acid. Methylation analysis of a representative LOS (L2) confirmed that NeuNAc is 2→3 linked to Gal. Thus, these LOSs structurally mimic certain glycolipids, i.e., paragloboside (LNnT-ceramide) and sialylparagloboside and some glycoproteins in having LNnT and N-acetyllactosamine sequences, respectively, with or without α2→3 linked NeuNAc. The molecular mimicry of the LOSs may play a role in the pathogenesis of N.meningitidis by assisting the organism to evade host immune defenses in man.
LPS, structure, core, Lipooligosaccharide, Neisseria meningitidis, Neisseria, terminal, characterization, neuraminic acid, lactosamine, sequence
NCBI PubMed ID: 9499383Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Division of Bacterial Products, Center for Biologics Evaluation and Research, FDA, Bethesda, MD, USA.
Methods: methylation, ELISA
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10. Compound ID: 532
a-D-Glcp-(1-3)-+
|
a-D-GlcpNAc-(1-2)-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)-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
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130659,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 120
Tsai C, Chen WH, Balakonis PA "Characterization of terminal NeuNAca2-3Galb1-4GlcNAc sequence in lipooligosaccharide of Neisseria meningitidis" -
Glycobiology 8(4) (1998) 359-365
Group B and C Neisseria meningitidis are the major cause of meningococcal disease in the United States and in Europe. N . meningitidis lipooligosaccharide (LOS), a major surface antigen, can be divided into 12 immunotypes of which L1 through L8 were found among Group B and C organisms. Groups B and C but not Group A may sialylate their LOSs with N-acetylneuraminic acid (NeuNAc) at the nonreducing end because they synthesize CMP-NeuNAc. Using sialic acid-galactose binding lectins as probes in an ELISA format, six of the eight LOS immunotypes (L2, L3, L4, L5, L7, and L8) in Groups B and C bound specifically to Maackia amurensis leukoagglutinin (MAL), which recognizes NeuNAcα2-3Galβ1-4GlcNAc/Glc sequence, but not to Sambucus nigra agglutinin, which binds NeuNAcα2-6Gal sequence. The combination of SDS-PAGE and MAL-blot analyses revealed that these six LOSs contained only the NeuNAcα2-3Galβ1-4GlcNAc trisaccharide sequence in their 4.1 kDa LOS components, which have a common terminal lacto-N-neotetraose (LNnT, Galβ1-4GlcNAcβ1-3Galβ1-4Glc) structure when nonsialylated as shown by previous studies. The LOS-lectin binding was abolished when the LOSs were treated with Newcastle disease viral neuraminidase which cleaves α2→3 linked sialic acid. Methylation analysis of a representative LOS (L2) confirmed that NeuNAc is 2→3 linked to Gal. Thus, these LOSs structurally mimic certain glycolipids, i.e., paragloboside (LNnT-ceramide) and sialylparagloboside and some glycoproteins in having LNnT and N-acetyllactosamine sequences, respectively, with or without α2→3 linked NeuNAc. The molecular mimicry of the LOSs may play a role in the pathogenesis of N.meningitidis by assisting the organism to evade host immune defenses in man.
LPS, structure, core, Lipooligosaccharide, Neisseria meningitidis, Neisseria, terminal, characterization, neuraminic acid, lactosamine, sequence
NCBI PubMed ID: 9499383Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Division of Bacterial Products, Center for Biologics Evaluation and Research, FDA, Bethesda, MD, USA.
Methods: methylation, ELISA
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11. Compound ID: 1082
a-D-GlcpNAc-(1-2)-+ b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+
| | |
EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_139427,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_419431,IEDB_419432,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 328
Monteiro MA, Fortuna-Nevin M, Farley J, Pavliak V "Phase-variation of the truncated lipo-oligosaccharide of Neisseria meningitidis NMB phosphoglucomutase isogenic mutant NMB-R6" -
Carbohydrate Research 338(24) (2003) 2905-2912
The detection of antibodies specific to meningococcal lipo-oligosaccharides (LOSs; outer-core→inner-core→lipid A) in sera of patients convalescent from meningococcal infection suggests the potential use of LOS as a vaccine to combat pathogenic Neisseria spp. Removal of the outer-core region, which expresses glycans homologous to human blood-group antigens, is a required first-step in order to avoid undesirable immunological reactions following vaccination. To this end, we describe here the structural makeup of the LOS produced by serogroup B N. meningitidis NMB isogenic phosphoglucomutase (Pgm) mutant (NMB-R6). The dominant LOS types produced by NMB-R6 expressed a deep-truncated inner-core region, GlcNAc-(1→2)-LDHepII-(1→3)-LDHepI-(1→5)-[Kdo 2→4]-Kdo → lipid A, with one PEA unit attached at either O-6 or O-7 of LDHepII, or with two simultaneously PEA moieties attached at O-3 and O-6 or O-3 and O-7 of the same unit. Unexpectedly, this mutation did not completely deactivate the production of Glc, as some LOS molecules were observed to carry Glc at O-4 of LDHepI and at O-3 of LDHepII. A glycoconjugate vaccine comprised of NMB-R6 LOSs is currently being evaluated in our laboratory.
Phase variation, Lipooligosaccharide, Neisseria meningitidis, Neisseria, mutant, PAGE, 2-aminoethyl phosphate, phosphoglucomutase, vaccine, lipo-oligosaccharide, isogenic
NCBI PubMed ID: 14667712Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Wyeth Vaccines Research, 211 Bailey Road, West Henrietta, NY 14586, USA
Methods: 1H NMR, GLC-MS, de-O-acylation, 31P NMR, ESI-MS, mild acid hydrolysis, PAGE
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12. Compound ID: 1083
a-D-GlcpNAc-(1-2)-+ b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+
| | |
EtN-(1--P--7)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 328
Monteiro MA, Fortuna-Nevin M, Farley J, Pavliak V "Phase-variation of the truncated lipo-oligosaccharide of Neisseria meningitidis NMB phosphoglucomutase isogenic mutant NMB-R6" -
Carbohydrate Research 338(24) (2003) 2905-2912
The detection of antibodies specific to meningococcal lipo-oligosaccharides (LOSs; outer-core→inner-core→lipid A) in sera of patients convalescent from meningococcal infection suggests the potential use of LOS as a vaccine to combat pathogenic Neisseria spp. Removal of the outer-core region, which expresses glycans homologous to human blood-group antigens, is a required first-step in order to avoid undesirable immunological reactions following vaccination. To this end, we describe here the structural makeup of the LOS produced by serogroup B N. meningitidis NMB isogenic phosphoglucomutase (Pgm) mutant (NMB-R6). The dominant LOS types produced by NMB-R6 expressed a deep-truncated inner-core region, GlcNAc-(1→2)-LDHepII-(1→3)-LDHepI-(1→5)-[Kdo 2→4]-Kdo → lipid A, with one PEA unit attached at either O-6 or O-7 of LDHepII, or with two simultaneously PEA moieties attached at O-3 and O-6 or O-3 and O-7 of the same unit. Unexpectedly, this mutation did not completely deactivate the production of Glc, as some LOS molecules were observed to carry Glc at O-4 of LDHepI and at O-3 of LDHepII. A glycoconjugate vaccine comprised of NMB-R6 LOSs is currently being evaluated in our laboratory.
Phase variation, Lipooligosaccharide, Neisseria meningitidis, Neisseria, mutant, PAGE, 2-aminoethyl phosphate, phosphoglucomutase, vaccine, lipo-oligosaccharide, isogenic
NCBI PubMed ID: 14667712Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Wyeth Vaccines Research, 211 Bailey Road, West Henrietta, NY 14586, USA
Methods: 1H NMR, GLC-MS, de-O-acylation, 31P NMR, ESI-MS, mild acid hydrolysis, PAGE
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13. Compound ID: 1091
a-D-GlcpNAc-(1-2)-+ b-D-Glcp-(1-4)-+
| |
EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
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a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_419431,IEDB_419432,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 328
Monteiro MA, Fortuna-Nevin M, Farley J, Pavliak V "Phase-variation of the truncated lipo-oligosaccharide of Neisseria meningitidis NMB phosphoglucomutase isogenic mutant NMB-R6" -
Carbohydrate Research 338(24) (2003) 2905-2912
The detection of antibodies specific to meningococcal lipo-oligosaccharides (LOSs; outer-core→inner-core→lipid A) in sera of patients convalescent from meningococcal infection suggests the potential use of LOS as a vaccine to combat pathogenic Neisseria spp. Removal of the outer-core region, which expresses glycans homologous to human blood-group antigens, is a required first-step in order to avoid undesirable immunological reactions following vaccination. To this end, we describe here the structural makeup of the LOS produced by serogroup B N. meningitidis NMB isogenic phosphoglucomutase (Pgm) mutant (NMB-R6). The dominant LOS types produced by NMB-R6 expressed a deep-truncated inner-core region, GlcNAc-(1→2)-LDHepII-(1→3)-LDHepI-(1→5)-[Kdo 2→4]-Kdo → lipid A, with one PEA unit attached at either O-6 or O-7 of LDHepII, or with two simultaneously PEA moieties attached at O-3 and O-6 or O-3 and O-7 of the same unit. Unexpectedly, this mutation did not completely deactivate the production of Glc, as some LOS molecules were observed to carry Glc at O-4 of LDHepI and at O-3 of LDHepII. A glycoconjugate vaccine comprised of NMB-R6 LOSs is currently being evaluated in our laboratory.
Phase variation, Lipooligosaccharide, Neisseria meningitidis, Neisseria, mutant, PAGE, 2-aminoethyl phosphate, phosphoglucomutase, vaccine, lipo-oligosaccharide, isogenic
NCBI PubMed ID: 14667712Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Wyeth Vaccines Research, 211 Bailey Road, West Henrietta, NY 14586, USA
Methods: 1H NMR, GLC-MS, de-O-acylation, 31P NMR, ESI-MS, mild acid hydrolysis, PAGE
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14. Compound ID: 1092
a-D-GlcpNAc-(1-2)-+ b-D-Glcp-(1-4)-+
| |
EtN-(1--P--7)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
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a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 328
Monteiro MA, Fortuna-Nevin M, Farley J, Pavliak V "Phase-variation of the truncated lipo-oligosaccharide of Neisseria meningitidis NMB phosphoglucomutase isogenic mutant NMB-R6" -
Carbohydrate Research 338(24) (2003) 2905-2912
The detection of antibodies specific to meningococcal lipo-oligosaccharides (LOSs; outer-core→inner-core→lipid A) in sera of patients convalescent from meningococcal infection suggests the potential use of LOS as a vaccine to combat pathogenic Neisseria spp. Removal of the outer-core region, which expresses glycans homologous to human blood-group antigens, is a required first-step in order to avoid undesirable immunological reactions following vaccination. To this end, we describe here the structural makeup of the LOS produced by serogroup B N. meningitidis NMB isogenic phosphoglucomutase (Pgm) mutant (NMB-R6). The dominant LOS types produced by NMB-R6 expressed a deep-truncated inner-core region, GlcNAc-(1→2)-LDHepII-(1→3)-LDHepI-(1→5)-[Kdo 2→4]-Kdo → lipid A, with one PEA unit attached at either O-6 or O-7 of LDHepII, or with two simultaneously PEA moieties attached at O-3 and O-6 or O-3 and O-7 of the same unit. Unexpectedly, this mutation did not completely deactivate the production of Glc, as some LOS molecules were observed to carry Glc at O-4 of LDHepI and at O-3 of LDHepII. A glycoconjugate vaccine comprised of NMB-R6 LOSs is currently being evaluated in our laboratory.
Phase variation, Lipooligosaccharide, Neisseria meningitidis, Neisseria, mutant, PAGE, 2-aminoethyl phosphate, phosphoglucomutase, vaccine, lipo-oligosaccharide, isogenic
NCBI PubMed ID: 14667712Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Wyeth Vaccines Research, 211 Bailey Road, West Henrietta, NY 14586, USA
Methods: 1H NMR, GLC-MS, de-O-acylation, 31P NMR, ESI-MS, mild acid hydrolysis, PAGE
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15. Compound ID: 1440
b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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a-D-GlcpNAc-(1-2)-+ |
| |
b-D-Galp-(1-4)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_419430,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 454
Kubo H, Ishii K, Koshino H, Toubetto K, Naruchi K, Yamasaka R "Synthesis of a 3,4-di-O-substituted heptose structure: A partial oligosaccharide expressed in neisserial lipooligosaccharide" -
European Journal of Organic Chemistry (6) (2004) 1202-1213
We have synthesized a tetrasaccharide containing a 3,4-dibranched L-glycero-D-manno-heptose (Hep), a-lactosyl-(1-4)-[L-a-D-Hep-(1-3)]-L-a-D-Hep 19, by using a mannose (Man) derivative as an acceptor. Prior to the construction of the branched Hep, we confirmed that the 3,4-dibranched Man structure could be synthesized using a 3-branched Man 6 as an acceptor. Glycosylation of the acceptor 6 using hepta-O-acetyl-a-lactosyl trichloroacetimidate (7) gave the desired 3,4-dibranched structure, a-lactosyl-(1-4)-[a-Man-(1-3)]-a-Man 8. As expected, a-lactosyl-(1-4)-[L-a-D-Hep-(1-3)]-a-D-Man 14 was also obtained by glycosylating the 4-OH acceptor 13 with 7 in a similar manner. The Man residue of 14 was converted into the Hep unit by Swern oxidation, Grignard reaction, and oxidative cleavage followed by reduction. Thus, we constructed the 3,4-dibranched Hep structure 19 by using the 3-branched Man 13 as an acceptor. The current results demonstrate that the gauche orientation of the O-3 and O-4 units of the Man configuration does not prevent the formation of the 3,4-di-O-substituted structure. This approach should provide an alternative method to synthesize the 3,4-dibranched Hep structure expressed in LOS produced by pathogenic Gram-negative bacteria such as the Neisserial and Haemophilus species.
lipopolysaccharides, Neisseria, Oligosaccharides, lipooligosaccharides, glycosylation
Publication DOI: 10.1002/ejoc.200300651Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: yamasaki@muses.tottori-u.ac.jp
Institutions: Department of Biochemistry & Biotechnology, Tottori University Koyama-Minami 4-101 Tottori City, Tottori-Ken 680-8553, Japan, The Institute of Physical and Chemical Research (RIKEN) Wako-shi, Saitama 351-0198, Japan, Maruho Co Ltd., Central Research Laboratory Shimogyo-ku, Kyoto 600-8815, Japan
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