Found 42 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
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1. Compound ID: 83
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Subst-(1-5)-+
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?%a-Kdop-(2-4)-+ |
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/Variants 0/-a-Kdop-(2-4)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
EtN-(1-0)-?%P-?)-
OR (exclusively)
?%Rhap-(1-?)-
Subst = core oligosaccharide |
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Structure type: oligomer
Aglycon: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_136105,IEDB_137777,IEDB_137778,IEDB_1394181,IEDB_150901,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 17
Bode CE, Brabetz W, Brade H "Cloning and characterization of 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) transferase genes (kdtA) from Acinetobacter baumannii and Acinetobacter haemolyticus" -
European Journal of Biochemistry 254(2) (1998) 404-412
3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) transferases (KdtA) are multifunctional glycosyltransferases with primary structures of low similarity. Totally degenerated primers were deduced from two stretches of identical amino acids between known KdtA sequences and used to amplify by PCR a kdtA-specific fragment from Acinetobacter baumannii ATCC 15308 DNA which was then applied as a probe for the cloning and sequencing of the complete Kdo transferase gene. With conserved PCR primers for this structural gene from A. baumannii ATCC 15308, also kdtA genes of A. baumannii ATCC 19606 and A. haemolyticus ATCC 17906 were obtained, cloned from the chromosome and sequenced. The genes coded for proteins with similarities to known Kdo transferases. Within the genus Acinetobacter, the identity and similarity of the deduced amino acid sequences were 71% and 84.5%, respectively. The kdtA sequences of both A. baumannii strains were identical and possessed a TTG start codon, whereas ATG was found in the case of A. haemolyticus. The genes from Acinetobacter and kdtA from Escherichia coli K-12 were expressed in the Gram-positive bacterium Corynebacterium glutamicum. In vitro tests confirmed the function of the gene products as Kdo transferases, which transferred mainly two Kdo residues to a synthetic lipid A precursor of E. coli. Also, no differences between the cloned kdtA genes from A. baumanniii, A. haemnolyticus and E. coli were observed when tetraacyl or hexaacyl lipid A were tested, since all transferases acted more efficiently on the former. With limiting amounts of acceptor, all Kdo transferases were able to transfer a third Kdo residue with varying efficiency
gene, characterization, 3-deoxy-D-manno-oct-2-ulosonic acid, acid, Acinetobacter, Acinetobacter baumannii, Acinetobacter haemolyticus, cloning, Kdo, lipopolysaccharide biosynthesis, shuttle plasmid, transferase
NCBI PubMed ID: 9660198Publication DOI: 10.1046/j.1432-1327.1998.2540404.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: hbrade@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
Methods: PCR, DNA sequencing, DNA cloning
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2. Compound ID: 912
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-?)-+
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
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3. Compound ID: 913
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-?)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
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4. Compound ID: 914
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-?)-+
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
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5. Compound ID: 2987
Structure type: oligomer
Trivial name: core-lipid A carbohydrate backbone
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_137340,IEDB_137778,IEDB_140957,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1027
Müller-Loennies S, Brade L, Brade H "Chemical structure and immunoreactivity of the lipopolysaccharide of the deep rough mutant I-69 Rd--/b+ of Haemophilus influenzae" -
European Journal of Biochemistry 269(4) (2002) 1237-1242
From the lipopolysaccharide of the deep rough mutant I-69 Rd--/b+ of Haemophilus influenzae two oligosaccharides were obtained after de-O-acylation and separation by high-performance anion exchange chromatography. Theirblankchemical structures were determined by one- and two-dimensional 1H-, 13C- and 31P-NMR spectroscopy as αKdo-4P-(2→6)-βGlcN-4P-(1→6)-αGlcN-1P and αKdo-5P-(2→6)-βGlcN-4P-(1→6)-αGlcN-1P. The specificity of mAbs S42-21 and S42-16 specific for Kdo-4P or Kdo- 5P, respectively [Rozalski, A., Brade L., Kosma P., Moxon R., Kusumoto S., & Brade H. (1997). Mol. Microbiol. 23, 569-577] was confirmed with neoglycoconjugates obtained by conjugation of the isolated oligosaccharides to BSA. In addition, a mAb S42-10-8 with unknown epitope specificity could be assigned using the neoglycoconjugates described herein. This mAb binds to an epitope composed of the bisphosphorylated glucosamine backbone of lipid A and Kdo-4P, whereby the latter determines the specificity strictly by the position of the phosphate group
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, oligosaccharide, structure, group, Research, Kdo, epitope, lipid, lipid A, phosphate, Oligosaccharides, MAb, specific, mutant, specificity, chemical, chemical structure, position, medicine, spectroscopy, backbone, rough, chromatography, separation, exchange, Glucosamine, acylation, two-dimensional, epitope specificity, anion-exchange, BSA, anion, immunoreactivity, neoglycoconjugate
NCBI PubMed ID: 11856357Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: hbrade@fz-borstel.de
Institutions: Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
Methods: serological methods
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6. Compound ID: 3164
Structure type: monomer
Contained glycoepitopes: IEDB_130650,IEDB_137778
The structure is contained in the following publication(s):
- Article ID: 1155
Rozalski A, Brade L, Kosma P, Moxon R, Kusumoto S, Brade H "Characterization of monoclonal antibodies recognizing three distinct, phosphorylated carbohydrate epitopes in the lipopolysaccharide of the deep rough mutant I-69 Rd-/b+ of Haemophilus influenzae" -
Molecular Microbiology 23(3) (1997) 569-577
Monoclonal antibodies against the lipopolysaccharide (LPS) of the deep rough mutant I-69 Rd-/b+ of Haemophilus influenzae were obtained after immunization of mice with sheep erythrocytes which had been coated with de-O-acylated LPS. Characterization of antibodies was performed by enzyme immuno assay (EIA) using LPS or neoglycoconjugates containing partial structures of LPS as solid-phase antigens and by haemagglutination with sheep erythrocytes coated with de-O-acylated LPS. Binding data were confirmed by EIA inhibition experiments using deacylated LPS or synthetic partial structures thereof. Three antibodies were specific for 3-deoxy-D-manno-octulopyranosonic acid- (Kdo) 5-phosphate, one for Kdo-4-phosphate, and one required, in addition to a Kdo-phosphate, parts of the phosphorylated glucosamine backbone of lipid A. All antibodies also bound in (i) Western blots to bacterial whole-cell lysates or isolated LPS separated by SDS-PAGE, (ii) bacterial colony blots, and (iii) immunofluorescence with live bacteria. The latter result indicated that Kdo-4- and Kdo-5-phosphate are synthesized by the bacteria and are not the result of phosphate migration
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, LPS, characterization, carbohydrate, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, mutant, phosphorylated, rough
NCBI PubMed ID: 9044290Journal NLM ID: 8712028Publisher: Blackwell Publishing
Institutions: Institute of Chemistry, University of Agriculture, A-1190 Vienna, Austria, Division of Biochemical Microbiology, Research Centre Borstel, Centre for Medicine and Biosciences, D-23845 Borstel, Germany, Institute of Molecular Medicine, John Radkliffe Hospital, Headington, Oxford OX3 9DU, UK, Departament of Chemistry, Faculty of Science, Osaka Univercity, Toyonaka, Osaka 570, Japan
Methods: SDS-PAGE, EIA, Western blotting
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7. Compound ID: 3169
Structure type: oligomer
Aglycon: (CH2)3S(CH2)2NHCSNH-BSA
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137778,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1155
Rozalski A, Brade L, Kosma P, Moxon R, Kusumoto S, Brade H "Characterization of monoclonal antibodies recognizing three distinct, phosphorylated carbohydrate epitopes in the lipopolysaccharide of the deep rough mutant I-69 Rd-/b+ of Haemophilus influenzae" -
Molecular Microbiology 23(3) (1997) 569-577
Monoclonal antibodies against the lipopolysaccharide (LPS) of the deep rough mutant I-69 Rd-/b+ of Haemophilus influenzae were obtained after immunization of mice with sheep erythrocytes which had been coated with de-O-acylated LPS. Characterization of antibodies was performed by enzyme immuno assay (EIA) using LPS or neoglycoconjugates containing partial structures of LPS as solid-phase antigens and by haemagglutination with sheep erythrocytes coated with de-O-acylated LPS. Binding data were confirmed by EIA inhibition experiments using deacylated LPS or synthetic partial structures thereof. Three antibodies were specific for 3-deoxy-D-manno-octulopyranosonic acid- (Kdo) 5-phosphate, one for Kdo-4-phosphate, and one required, in addition to a Kdo-phosphate, parts of the phosphorylated glucosamine backbone of lipid A. All antibodies also bound in (i) Western blots to bacterial whole-cell lysates or isolated LPS separated by SDS-PAGE, (ii) bacterial colony blots, and (iii) immunofluorescence with live bacteria. The latter result indicated that Kdo-4- and Kdo-5-phosphate are synthesized by the bacteria and are not the result of phosphate migration
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, LPS, characterization, carbohydrate, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, mutant, phosphorylated, rough
NCBI PubMed ID: 9044290Journal NLM ID: 8712028Publisher: Blackwell Publishing
Institutions: Institute of Chemistry, University of Agriculture, A-1190 Vienna, Austria, Division of Biochemical Microbiology, Research Centre Borstel, Centre for Medicine and Biosciences, D-23845 Borstel, Germany, Institute of Molecular Medicine, John Radkliffe Hospital, Headington, Oxford OX3 9DU, UK, Departament of Chemistry, Faculty of Science, Osaka Univercity, Toyonaka, Osaka 570, Japan
Methods: SDS-PAGE, EIA, Western blotting
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8. Compound ID: 3170
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P-5)-+ P-4)-+
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P-4)-a-Kdo-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1---P---/BSA/ |
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Structure type: oligomer
Aglycon: BSA
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_137340,IEDB_137777,IEDB_137778,IEDB_140956,IEDB_140957,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1155
Rozalski A, Brade L, Kosma P, Moxon R, Kusumoto S, Brade H "Characterization of monoclonal antibodies recognizing three distinct, phosphorylated carbohydrate epitopes in the lipopolysaccharide of the deep rough mutant I-69 Rd-/b+ of Haemophilus influenzae" -
Molecular Microbiology 23(3) (1997) 569-577
Monoclonal antibodies against the lipopolysaccharide (LPS) of the deep rough mutant I-69 Rd-/b+ of Haemophilus influenzae were obtained after immunization of mice with sheep erythrocytes which had been coated with de-O-acylated LPS. Characterization of antibodies was performed by enzyme immuno assay (EIA) using LPS or neoglycoconjugates containing partial structures of LPS as solid-phase antigens and by haemagglutination with sheep erythrocytes coated with de-O-acylated LPS. Binding data were confirmed by EIA inhibition experiments using deacylated LPS or synthetic partial structures thereof. Three antibodies were specific for 3-deoxy-D-manno-octulopyranosonic acid- (Kdo) 5-phosphate, one for Kdo-4-phosphate, and one required, in addition to a Kdo-phosphate, parts of the phosphorylated glucosamine backbone of lipid A. All antibodies also bound in (i) Western blots to bacterial whole-cell lysates or isolated LPS separated by SDS-PAGE, (ii) bacterial colony blots, and (iii) immunofluorescence with live bacteria. The latter result indicated that Kdo-4- and Kdo-5-phosphate are synthesized by the bacteria and are not the result of phosphate migration
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, LPS, characterization, carbohydrate, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, mutant, phosphorylated, rough
NCBI PubMed ID: 9044290Journal NLM ID: 8712028Publisher: Blackwell Publishing
Institutions: Institute of Chemistry, University of Agriculture, A-1190 Vienna, Austria, Division of Biochemical Microbiology, Research Centre Borstel, Centre for Medicine and Biosciences, D-23845 Borstel, Germany, Institute of Molecular Medicine, John Radkliffe Hospital, Headington, Oxford OX3 9DU, UK, Departament of Chemistry, Faculty of Science, Osaka Univercity, Toyonaka, Osaka 570, Japan
Methods: SDS-PAGE, EIA, Western blotting
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9. Compound ID: 3235
Structure type: monomer
Aglycon: Allyl or 3-(2-aminoethylthio)propyl
Contained glycoepitopes: IEDB_130650,IEDB_137778
The structure is contained in the following publication(s):
- Article ID: 1184
Sekljic H, Kosma P, Bartek J, Fukase K, Kusumoto S, Brade H "Synthesis of neoglycoproteins containing 5-OX-phosphorylated Kdo-monosaccharide, 4-O- and 5-O-phosphorylated a-Kdo-(2->6)-2-acetamido-2-deoxy-b-D-glycopyranosyl disaccharide residues" -
Journal of Endotoxin Research 3 (1996) 164-151
Lipopolysaccharide, synthesis, LPS, core, Kdo, phosphate, protein, disaccharide, neoglycoprotein, neoglycoproteins, conjugate, BSA
Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Chemistry, University of Agriculture, Vienna,Avstria, Department of Chemistry, University of Agriculture, Vienna,Avstria
Methods: NMR
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10. Compound ID: 3239
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P-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1--/Allyl or 3-(2-aminoethylthio)propyl/ |
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Structure type: oligomer
Aglycon: Allyl or 3-(2-aminoethylthio)propyl
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137778,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1184
Sekljic H, Kosma P, Bartek J, Fukase K, Kusumoto S, Brade H "Synthesis of neoglycoproteins containing 5-OX-phosphorylated Kdo-monosaccharide, 4-O- and 5-O-phosphorylated a-Kdo-(2->6)-2-acetamido-2-deoxy-b-D-glycopyranosyl disaccharide residues" -
Journal of Endotoxin Research 3 (1996) 164-151
Lipopolysaccharide, synthesis, LPS, core, Kdo, phosphate, protein, disaccharide, neoglycoprotein, neoglycoproteins, conjugate, BSA
Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Chemistry, University of Agriculture, Vienna,Avstria, Department of Chemistry, University of Agriculture, Vienna,Avstria
Methods: NMR
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11. Compound ID: 3242
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P-5)-+
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L-gro-a-D-manHepp-(1-4)-a-Kdop-(2--/Allyl or 3-(2-aminoethylthio)propyl)/ |
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Structure type: oligomer
Aglycon: Allyl or 3-(2-aminoethylthio)propyl)
Contained glycoepitopes: IEDB_130650,IEDB_137778,IEDB_2189047
The structure is contained in the following publication(s):
- Article ID: 1185
Sekljic H, Wimmer N, Hofinger A, Brade H, Kosma P "Synthesis of neoglycoprotreins containing L-glycero-a-D-manno-heptopyranosyl-(1->4)- and -(1->5)-linked 3-deoxy-a-D-manno-oct-2-ulopyranosylonic acid (Kdo) phosphate determinants" -
Journal of the Chemical Society, Perkin Transactions 1 (1997) 1973-1982
The disaccharide allyl glycosides 4, 8, 13 and the trisaccharide 33 have been prepared using heptopyranosyltrichloroacetimidate 1 or the disaccharide bromide 27 as glycosyl donors followed by efficientO-phosphorylation via the amidite procedure. The allyl glycosides 4, 8 and 33 are converted into3-(2-aminoethylthio)propyl glycosides and are coupled to bovine serum albumin. The resultingneoglycoconjugates 6 and 35 containing spacer-linked Hep-(1Æ4)-Kdo and Hep-(1Æ5)-Kdo 4-phosphate-(2Æ6)-‚-GlcNAc residues correspond to part structures of the inner core region in bacteriallipopolysaccharide, whereas compound 10 contains the artificial analogue Hep-(1Æ4)-Kdo 5-phosphate.The compounds may be used in immunochemical characterisation of monoclonal antibodies.
synthesis, core, heptose, determinant, acid, Kdo, phosphate, neoglycoprotein, neoglycoconjugate
Publication DOI: 10.1039/A700497DJournal NLM ID: 7505598Publisher: Chemical Society
Institutions: Institute of Chemistry, University of Agricultural Sciences, Vienna, A-1190 Muthgasse, Austria, Research Center Borstel, Borstel, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, 31P NMR, chemical synthesis, optical rotation measurement
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12. Compound ID: 3388
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ EtN-(1---P---P---?)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-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_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 1270
Sun S, Scheffler NK, Gibson BW, Wang J, Munson RS "Identification and characterization of the N-acetylglucosamine glycosyltransferase gene of Haemophilus ducreyi" -
Infection and Immunity 70(10) (2002) 5887-5892
Haemophilus ducreyi is the causative agent of chancroid, a sexually transmitted ulcerative disease. In the present study, the Neisseria gonorrhoeas IgtA lipooligosaccharide glycosyltransferase gene was used to identify a homologue in the genome ofH. ducreyi. The putative H. ducreyi glycosyltransferase gene (designated IgtA) was cloned and insertionally inactivated, and an isogenic mutant was constructed. Structural studies demonstrated that the lipooligosaccharide isolated from the mutant strain lacked N-acetylglucosamine and distal sugars found in the lipooligosaccharide produced by the parental strain. The isogenic mutant was transformed with a recombinant plasmid containing the putative glycosyltransferase gene. This strain produced the lipooligosaccharide glycoforms produced by the parental strain, confirming that the IgtA gene encodes the N-acetyl-glucosamine glycosyltransferase.
biosynthesis, Haemophilus, lipopolysaccharides, Haemophilus ducreyi, chemistry, gene, Bacterial, genetics, human, DNA, Support, Non-U.S.Gov't, characterization, identification, molecular, cloning, Carbohydrate Sequence, Molecular Sequence Data, Genes, spectrometry, mutation, agent, glycosyltransferase, Base Sequence, N-acetylglucosamine, U.S.Gov't, Matrix-Assisted Laser Desorption-Ionization, enzymology, Mass, P.H.S., chancroid, Genetic Complementation Test, N-Acetylglucosaminyltransferases
NCBI PubMed ID: 12228324Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: munsonr@pediatrics.ohio-state.edu
Institutions: Columbus Childrens Research Institute, Department of Pediatrics and Department of Molecular Virology, Immunology, and Medical Genetics, The Ohio State University, Columbus, Ohio 43205, Department of Pharmaceutical Chemistry, University of California, San Francisco, California 941433, Buck Institute for Age Research, Novato, California 949454
Methods: MALDI-TOF MS, genetic methods, cloning
- Article ID: 1271
Sun SH, Schilling B, Tarantino L, Tullius MV, Gibson BW, Munson RS "Cloning and characterization of the lipooligosaccharide galactosyltransferase II gene of Haemophilus ducreyi" -
Journal of Bacteriology 182(8) (2000) 2292-2298
Haemophilus ducreyi is the etiologic agent of chancroid, a genital ulcer disease. The lipooligosaccharide (LOS) is considered to be a major virulence determinant and has been implicated in the adherence of H. ducreyi to keratinocytes. Strain A77, an isolate from the Paris collection, is serum sensitive, poorly adherent to fibroblasts, and deficient in microcolony formation. Structural analysis indicates that the LOS of strain A77 lacks the galactose residue found in the N-acetyllactosamine portion of the strain 35000HP LOS as well as the sialic acid substitution. From an H. ducreyi 35000HP genomic DNA library, a clone complementing the defect in A77 was identified by immunologic screening with monoclonal antibody (MAb) 3F11, a MAb which recognizes the N-acetyllactosamine portion of strain 35000HP LOS. The clone contained a 4-kb insert that was sequenced. One open reading frame which encodes a protein with a molecular weight of 33,400 was identified. This protein has homology to glycosyltransferases of Haemophilus influenzae, Haemophilus somnus, Neisseria species, and Pasteurella haemolytica. The putative H. ducreyi glycosyltransferase gene was insertionally inactivated, and an isogenic mutant of strain 35000HP was constructed. The most complex LOS glycoform produced by the mutant has a mobility on sodium dodecyl sulfate-polyacrylamide gel identical to that of the LOS of strain A77 and lacks the 3F11-binding epitope. Structural studies confirm that the most complex glycoform of the LOS isolated from the mutant lacks the galactose residue found in the N-acetyllactosamine portion of the strain 35000HP LOS. Although previously published data suggested that the serum-sensitive phenotype of A77 was due to the LOS mutation, we observed that the complemented A77 strain retained its serum-sensitive phenotype and that the galactosyltransferase mutant retained its serum-resistant phenotype. Thus, the serum sensitivity of strain A77 cannot be attributed to the galactosyltransferase mutation in strain A77.
Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, gene, characterization, cloning, galactosyltransferase
NCBI PubMed ID: 10735874Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: munsonr+AEA-pediatrics.ohio-state.edu
Institutions: Children's Research Institute, Department of Pediatrics, and Department of Molecular Virology, Immunology and Medical Genetics, The Ohio State University, Columbus, Ohio 43205-2696, and Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA.
Methods: DNA sequencing, MALDI-TOF MS, genetic methods, Southern blotting, MALDI-PSD MS
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13. Compound ID: 3424
|
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ EtN-(1---P---P---?)-+
| |
b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-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_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1270
Sun S, Scheffler NK, Gibson BW, Wang J, Munson RS "Identification and characterization of the N-acetylglucosamine glycosyltransferase gene of Haemophilus ducreyi" -
Infection and Immunity 70(10) (2002) 5887-5892
Haemophilus ducreyi is the causative agent of chancroid, a sexually transmitted ulcerative disease. In the present study, the Neisseria gonorrhoeas IgtA lipooligosaccharide glycosyltransferase gene was used to identify a homologue in the genome ofH. ducreyi. The putative H. ducreyi glycosyltransferase gene (designated IgtA) was cloned and insertionally inactivated, and an isogenic mutant was constructed. Structural studies demonstrated that the lipooligosaccharide isolated from the mutant strain lacked N-acetylglucosamine and distal sugars found in the lipooligosaccharide produced by the parental strain. The isogenic mutant was transformed with a recombinant plasmid containing the putative glycosyltransferase gene. This strain produced the lipooligosaccharide glycoforms produced by the parental strain, confirming that the IgtA gene encodes the N-acetyl-glucosamine glycosyltransferase.
biosynthesis, Haemophilus, lipopolysaccharides, Haemophilus ducreyi, chemistry, gene, Bacterial, genetics, human, DNA, Support, Non-U.S.Gov't, characterization, identification, molecular, cloning, Carbohydrate Sequence, Molecular Sequence Data, Genes, spectrometry, mutation, agent, glycosyltransferase, Base Sequence, N-acetylglucosamine, U.S.Gov't, Matrix-Assisted Laser Desorption-Ionization, enzymology, Mass, P.H.S., chancroid, Genetic Complementation Test, N-Acetylglucosaminyltransferases
NCBI PubMed ID: 12228324Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: munsonr@pediatrics.ohio-state.edu
Institutions: Columbus Childrens Research Institute, Department of Pediatrics and Department of Molecular Virology, Immunology, and Medical Genetics, The Ohio State University, Columbus, Ohio 43205, Department of Pharmaceutical Chemistry, University of California, San Francisco, California 941433, Buck Institute for Age Research, Novato, California 949454
Methods: MALDI-TOF MS, genetic methods, cloning
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14. Compound ID: 3425
|
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ EtN-(1---P---P---?)-+
| |
b-D-Gal-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-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_130697,IEDB_135813,IEDB_136044,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1270
Sun S, Scheffler NK, Gibson BW, Wang J, Munson RS "Identification and characterization of the N-acetylglucosamine glycosyltransferase gene of Haemophilus ducreyi" -
Infection and Immunity 70(10) (2002) 5887-5892
Haemophilus ducreyi is the causative agent of chancroid, a sexually transmitted ulcerative disease. In the present study, the Neisseria gonorrhoeas IgtA lipooligosaccharide glycosyltransferase gene was used to identify a homologue in the genome ofH. ducreyi. The putative H. ducreyi glycosyltransferase gene (designated IgtA) was cloned and insertionally inactivated, and an isogenic mutant was constructed. Structural studies demonstrated that the lipooligosaccharide isolated from the mutant strain lacked N-acetylglucosamine and distal sugars found in the lipooligosaccharide produced by the parental strain. The isogenic mutant was transformed with a recombinant plasmid containing the putative glycosyltransferase gene. This strain produced the lipooligosaccharide glycoforms produced by the parental strain, confirming that the IgtA gene encodes the N-acetyl-glucosamine glycosyltransferase.
biosynthesis, Haemophilus, lipopolysaccharides, Haemophilus ducreyi, chemistry, gene, Bacterial, genetics, human, DNA, Support, Non-U.S.Gov't, characterization, identification, molecular, cloning, Carbohydrate Sequence, Molecular Sequence Data, Genes, spectrometry, mutation, agent, glycosyltransferase, Base Sequence, N-acetylglucosamine, U.S.Gov't, Matrix-Assisted Laser Desorption-Ionization, enzymology, Mass, P.H.S., chancroid, Genetic Complementation Test, N-Acetylglucosaminyltransferases
NCBI PubMed ID: 12228324Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: munsonr@pediatrics.ohio-state.edu
Institutions: Columbus Childrens Research Institute, Department of Pediatrics and Department of Molecular Virology, Immunology, and Medical Genetics, The Ohio State University, Columbus, Ohio 43205, Department of Pharmaceutical Chemistry, University of California, San Francisco, California 941433, Buck Institute for Age Research, Novato, California 949454
Methods: MALDI-TOF MS, genetic methods, cloning
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15. Compound ID: 3426
|
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ EtN-(1---P---P---?)-+
| |
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-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_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137778,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1270
Sun S, Scheffler NK, Gibson BW, Wang J, Munson RS "Identification and characterization of the N-acetylglucosamine glycosyltransferase gene of Haemophilus ducreyi" -
Infection and Immunity 70(10) (2002) 5887-5892
Haemophilus ducreyi is the causative agent of chancroid, a sexually transmitted ulcerative disease. In the present study, the Neisseria gonorrhoeas IgtA lipooligosaccharide glycosyltransferase gene was used to identify a homologue in the genome ofH. ducreyi. The putative H. ducreyi glycosyltransferase gene (designated IgtA) was cloned and insertionally inactivated, and an isogenic mutant was constructed. Structural studies demonstrated that the lipooligosaccharide isolated from the mutant strain lacked N-acetylglucosamine and distal sugars found in the lipooligosaccharide produced by the parental strain. The isogenic mutant was transformed with a recombinant plasmid containing the putative glycosyltransferase gene. This strain produced the lipooligosaccharide glycoforms produced by the parental strain, confirming that the IgtA gene encodes the N-acetyl-glucosamine glycosyltransferase.
biosynthesis, Haemophilus, lipopolysaccharides, Haemophilus ducreyi, chemistry, gene, Bacterial, genetics, human, DNA, Support, Non-U.S.Gov't, characterization, identification, molecular, cloning, Carbohydrate Sequence, Molecular Sequence Data, Genes, spectrometry, mutation, agent, glycosyltransferase, Base Sequence, N-acetylglucosamine, U.S.Gov't, Matrix-Assisted Laser Desorption-Ionization, enzymology, Mass, P.H.S., chancroid, Genetic Complementation Test, N-Acetylglucosaminyltransferases
NCBI PubMed ID: 12228324Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: munsonr@pediatrics.ohio-state.edu
Institutions: Columbus Childrens Research Institute, Department of Pediatrics and Department of Molecular Virology, Immunology, and Medical Genetics, The Ohio State University, Columbus, Ohio 43205, Department of Pharmaceutical Chemistry, University of California, San Francisco, California 941433, Buck Institute for Age Research, Novato, California 949454
Methods: MALDI-TOF MS, genetic methods, cloning
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