Found 261 structures.
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1. Compound ID: 793
Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_125615,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 206
Vyas NK, Vyas MN, Chervenak MC, Johnson MA, Pinto BM, Bundle DR, Quiocho FA "Molecular recognition of oligosaccharide epitopes by a monoclonal fab specific for Shigella flexneri Y lipopolysaccharide: X-ray structures and thermodynamics" -
Biochemistry 41(46) (2002) 13575-13586
The antigenic recognition of Shigella flexneri O-polysaccharide, which consists of a repeating unit ABCD [→2)-α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→], by the monoclonal antibody SYA/J6 (IgG3, kappa) has been investigated by crystallographic analysis of the Fab domain and its two complexes with two antigen segments (a pentasaccharide Rha A-Rha B-Rha C-GlcNAc D-Rha A' and a modified trisaccharide Rha B-Rha C-GlcNAc D in which Rha C is missing a C2-OH group). These complex structures, the first for a Fab specific for a periodic linear heteropolysaccharide, reveal a binding site groove (between the V(H) and V(L) domains) that makes polar and nonpolar contacts with all the sugar
Lipopolysaccharide, antigen, oligosaccharide, structure, repeating unit, trisaccharide, analysis, group, molecular, X-ray, Shigella flexneri, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, recognition, complex, epitopes, O-polysaccharide, O polysaccharide, specific, sugar, modified, Shigella, pentasaccharide, antigenic, binding, binding site, domain, domains, FAB, heteropolysaccharide, linear, molecular recognition, polar, site, thermodynamics
NCBI PubMed ID: 12427018Journal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: faq@bcm.tmc.edu
Institutions: Verna and Marrs Mclean Department of Biochemistry and Molecular Biology and Howard Hughes Medical Institute, Baylor College of Medicine, Houston, Texas 77030, Departments of Chemistry and of Molecular Biology and Biochemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6, Department of Chemistry, University of Alberta, Edmonton, AB, Canada
Methods: crystallography, thermodynamics
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2. Compound ID: 807
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a-L-Olip4Me-(1-3)-a-L-Fucp2Me4Pp-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerostate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerostate
Trivial name: phenolic glycolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 216
Watanabe M, Aoyagi Y, Ohta A, Minnikin DE "Structures of phenolic glycolipids from Mycobacterium kansasii" -
European Journal of Biochemistry 248(1) (1997) 93-98
From the lipid fraction of cells of Mycobacterium kansasii, four phenolic glycolipids K5, K6, K7 and K8, were isolated, in addition to three known phenolic glycolipids KI, KII and KIV. K5 was identified as a tetraglycosyl phenolic glycolipid whose sugar moiety was 2,6-dideoxy-4-O-methyl-L-α-arabinohexopyranosyl(1→3)-4-O-pro pionyl-2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamno pyranosyl-(1→3)-2,4-di-O-methyl-L-α-rhamnopyranosyl(1→) and phenolic glycolipid K6 as deacetyl-KI. Glycolipids K7 and K8 were triglycosyl phenolic glycolipids having the sugar moieties of 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2,4-di-O-methy-L-α-rhamnopyranosyl(1→) and 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→), respectively. Phenolic glycolipids K6 and K7 have been referred to as controlled degradation products of phenolic glycolipid KI previously. Also isolated was 5-mycolyl-β-arabinofuranosyl(1→2)-5-mycolyl-α-arabinofurnosyl(1→1')-glycerol, an analogue of glycolipid ai, originally isolated from Mycobacterium avium-Mycobacterium intracellulare complex, having mycolic acids of M. kansasii.
structure, isolation, glycolipid ai, Mycobacterium kansasii, phenolic glycolipid
NCBI PubMed ID: 9310365Publication DOI: 10.1111/j.1432-1033.1997.00093.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: motokoko@triton.ps.toyaku.ac.jp
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo, Japan, Department of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne, UK
Methods: NMR-2D, NMR
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3. Compound ID: 808
|
a-L-Olip4Me-(1-3)-a-L-Fucp2Me4Ac-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerostate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerostate
Trivial name: phenolic glycolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 216
Watanabe M, Aoyagi Y, Ohta A, Minnikin DE "Structures of phenolic glycolipids from Mycobacterium kansasii" -
European Journal of Biochemistry 248(1) (1997) 93-98
From the lipid fraction of cells of Mycobacterium kansasii, four phenolic glycolipids K5, K6, K7 and K8, were isolated, in addition to three known phenolic glycolipids KI, KII and KIV. K5 was identified as a tetraglycosyl phenolic glycolipid whose sugar moiety was 2,6-dideoxy-4-O-methyl-L-α-arabinohexopyranosyl(1→3)-4-O-pro pionyl-2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamno pyranosyl-(1→3)-2,4-di-O-methyl-L-α-rhamnopyranosyl(1→) and phenolic glycolipid K6 as deacetyl-KI. Glycolipids K7 and K8 were triglycosyl phenolic glycolipids having the sugar moieties of 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2,4-di-O-methy-L-α-rhamnopyranosyl(1→) and 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→), respectively. Phenolic glycolipids K6 and K7 have been referred to as controlled degradation products of phenolic glycolipid KI previously. Also isolated was 5-mycolyl-β-arabinofuranosyl(1→2)-5-mycolyl-α-arabinofurnosyl(1→1')-glycerol, an analogue of glycolipid ai, originally isolated from Mycobacterium avium-Mycobacterium intracellulare complex, having mycolic acids of M. kansasii.
structure, isolation, glycolipid ai, Mycobacterium kansasii, phenolic glycolipid
NCBI PubMed ID: 9310365Publication DOI: 10.1111/j.1432-1033.1997.00093.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: motokoko@triton.ps.toyaku.ac.jp
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo, Japan, Department of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne, UK
Methods: NMR-2D, NMR
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4. Compound ID: 2892
Structure type: oligomer
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,SB_7
The structure is contained in the following publication(s):
- Article ID: 1017
Mulard LA, Claudemans CPJ "Synthesis of specifically deoxygenated disaccharide derivatives of the Shigella dysenteriae type 1 O-antigen" -
Carbohydrate Research 274 (1995) 209-222
The synthesis of methyl O-α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosides specifically deoxygenated at position 2 (31), or 4 (21) of the rhamnopyranosyl residue was accomplished using methyl 3,4,6-tri-O-benzoyl-α-D-galactopyranoside (18) as the glycosyl acceptor. Phenyl thionocarbonate activation of the penta-O-benzoylated disaccharide precursor followed by Barton reduction and Zemplen transesterification gave 31, while 21 was obtained via condensation of the deoxygenated monosaccharide donor with 18, and subsequent debenzoylation of the product.
synthesis, O-antigen, O antigen, type, Shigella dysenteriae type 1, derivative, Shigella, disaccharide, Shigella dysenteriae, deoxygenated
NCBI PubMed ID: 7585707Journal NLM ID: 0043535Publisher: Elsevier
Institutions: NIDDK, National Institutes of Health, Bethesda, MD, USA
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5. Compound ID: 4797
|
a-D-Olip4Me-(1-3)-a-L-Fucp2Me4Ac-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerosate
Compound class: glycolipid
Contained glycoepitopes: IEDB_131184,IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1797
Hartmann S, Minnikin DE, Mallet AI, Ridell M, Rigouts L, Portaels F "Fast atom bombardment mass spectrometry of mycobacterial phenolic glycolipids" -
Biological Mass Spectrometry 23 (1994) 362-368
Fast atom bombardment mass spectra were successfully recorded for intact glycosylphenolphthiocerol dimycocerosates (phenolic glycolipids, PGLs) from Mycobacterium kansasii, M. leprae, M. tuberculosis, M. marinum, M. bovis and M. haemophilum. Characteristic fragment ions from the loss of the oligosaccharide moiety and one of the long-chain multimethyl-branched mycocerosic acids were observed in most cases. A tandem mass spectrometric experiment was carried out on the PGL from M. tuberculosis, revealing the type of mycocerosic acids esterified to individual homologues. Mass spectra of homologues separated by reversed-phase high-performance liquid chromatography gave information on the substitution pattern in certain cases. The potential of matrix-assisted laser desorption ionization spectroscopy was demonstrated by a successful analysis of the PGL from M. tuberculosis.
NCBI PubMed ID: 8038230Journal NLM ID: 9102982Institutions: Department of Chemistry, The University, Newcastle upon Tyne, UK
Methods: FAB-MS
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6. Compound ID: 4947
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a-L-Olip4Me-(1-3)-a-L-Fucp2Me4Ac-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me |
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Structure type: oligomer
Trivial name: mycoside A
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1905
Fournié JJ, Rivière M, Puzo G "A tetrasaccharidic structure for the carbohydrate moiety of the major phenolic glycolipid from Mycobacterium kansasii" -
Comptes Rendus de l'Academie des Sciences [French] 303 (1986) 1205-1207
Institutions: Centre de Recherche de Bwchimie et de Genitique Cellulaires du Centre National de la Recherche Scientifiqw, 118 route de Narbonne, 31 062 Toulouse Cedex, France
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7. Compound ID: 5328
|
a-D-Olip4Me-(1-3)-a-L-Fucp2Me4Ac-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/(->1) phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: (->1) phenolphthiocerol dimycocerosate
Compound class: glycolipid
Contained glycoepitopes: IEDB_131184,IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2207
Gurjar MK, Reddy KR "Synthesis of methyl 2,4-di-O-methyl-3-O-(2-O-methyl-a-L-rhamnopyranosyl)-a-L-rhamnopyranoside and methyl 2,4-diO-methyl-3-O-[2-O-methyl-3-O-(2-O-methyl-a-L-fucopyranosyl)-a-L-rhamnopyranosyl]-a-L-rhamnopyranoside: di and tri-saccharide segments of a phenolic glycolipids of Mycobacterium kansasii" -
Carbohydrate Research 226 (1992) 233-238
Syntheses of the title glycosides are described. The critical O-glycosylations were carried out in the presence of boron trifluoride etherate with a high degree of alpha-selectivity.
NCBI PubMed ID: 1617686Publication DOI: 10.1016/0008-6215(92)84070-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Indian Institute of Chemical Technology, Hyderabad
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8. Compound ID: 5510
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a-D-Olip4Me-(1-3)-a-L-Fucp2Me-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me |
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Structure type: oligomer
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2331
Vercellone A, Rivière M, Fournié JJ, Puzo G "Structural analogy between the major phenolic glycolipid antigens from two Mycobacteria species: kansasii and gastri" -
Chemistry and Physics of Lipids 48 (1988) 129-134
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9. Compound ID: 5930
|
a-Olip4Me-(1-3)-a-L-Fucp2Me4Ac-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerosate
Trivial name: mycoside A
Compound class: glycolipid
Contained glycoepitopes: IEDB_131184,IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2637
Fournié JJ, Rivière M, Puzo G "Structural elucidation of the major phenolic glycolipid from Mycobacterium kansasii. I. Evidence for tetrasaccharide structure of the oligosaccharide moiety" -
Journal of Biological Chemistry 262 (1987) 3174-3179
Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
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10. Compound ID: 8262
Structure type: oligomer
Trivial name: trisaccharide epitope
Contained glycoepitopes: IEDB_125615,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 3614
Auzanneau F, Bundle DR "Synthesis of chlorodeoxy trisaccharides related to the Shigella flexneri Y polysaccharide" -
Carbohydrate Research 247 (1993) 195-209
Chloromethoxylation of di-O-acetyl-L-rhamnal has been employed as a convenient route to methyl 3,4-di-O-acetyl-2-chloro-2-deoxy-α-L-rhamnopyranoside 7, which was converted into an ethyl thioglycoside 10, suitable for use as a glycosyl donor. It and a disaccharide analogue 20 were effective donors in N-iodosuccinimide-triflic acid promoted glycosylations of a 2-acetamido-2-deoxy-D-glucopyranoside acceptor 22. Chlorodeoxy saccharides have previously been shown to be suitable derivatives to probe oligosaccharide-protein interactions, and this synthetic strategy provided three monochlorodeoxy trisaccharide congeners of the native Shigella flexneri epitope 2, α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-β-D-GlcNAcp-(1→O)-Me.
synthesis, polysaccharide, trisaccharide, Shigella flexneri, derivative, Shigella, Trisaccharides
NCBI PubMed ID: 7693346Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario.
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical methods
- Article ID: 3621
Hanna HR, Bundle DR "Antibody-oligosaccharide interactions: the synthesis of 2-deoxy-a-L-rhamnose containing oligosaccharide haptens relataed to Shigella flexneri variant Y antigen" -
Canadian Journal of Chemistry 71(1) (1993) 125-134
A series of di- and trisaccharide glycosides based on the α-L-Rha(1→3)β-D-GlcNAc and α-L-Rha(1→3)α-L-Rha(1→3)β-D-GlcNAc elements have been synthesized to locate the minimal oligosaccharide determinant of the Shigella flexneri O-polysaccharide, which is built from a tetrasaccharide repeating unit, [→2)α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1-]n. These compounds also serve to identify the carbohydrate surface of the Shigella antigen that interacts with a monoclonal antibody, currently the subject of crystallographic studies. Two strategies utilizing suitably protected glycals 1 and 19 were employed to obtain analogs bearing either terminal or glycosylated 2,6-dideoxy-α-L-arabino-hexopyranosyl (2-deoxy-α-L-rhamnopyranosyl) residues. N-Iodosuccinimide activation of the glycals in the presence of selectively protected mono- and disaccharide alcohols afforded 2-deoxy-2-iodo-α-L-rhamnopyranosides and these were ultimately reduced during deprotection stages to afford the desired functionality. Di-O-acetyl L-rhamnal 1 reacted with monosaccharides 2 and 7, and with disaccharide 11, to yield disaccharides 4 and 8, and trisaccharide 12, each bearing a terminal 2-deoxy-α-L-rhamnopyranosyl residue. The selectively protected 3-O-benzoyl-4-O-benzyl-L-rhamnal 19 was synthesized from L-rhamnal and used to prepared trisaccharide 22, which contained an internal 2-deoxy-2-iodo-α-L-rhamnopyranosyl unit. Removal of protecting groups gave the oligosaccharides 6, 10, 14, and 23. Oligosaccharides that contained a 2-deoxy-α-L-rhamnopyranosyl residue showed enhanced inhibitory power: in the case of trisaccharide 23 a 1.8 kcal/mol relative increase in free energy of binding compared to a larger pentasaccharide epitope, α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1→2)α-L-Rhap-1→OMe. These data suggest that the rhamnose O-2 hydroxyl of residue C points toward and has important interactions with binding site amino acids.
synthesis, Shigella flexneri, monoclonal antibodies, O-polysaccharide, binding site, antigen-antibody interaction, 2-deoxy-L-rhamnose
Publication DOI: 10.1139/v93-018Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6 Canada
Methods: 13C NMR, 1H NMR, TLC, ELISA, chemical methods, serological methods
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11. Compound ID: 8276
Structure type: oligomer
Trivial name: trisaccharide epitope
Contained glycoepitopes: IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_143253,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 3621
Hanna HR, Bundle DR "Antibody-oligosaccharide interactions: the synthesis of 2-deoxy-a-L-rhamnose containing oligosaccharide haptens relataed to Shigella flexneri variant Y antigen" -
Canadian Journal of Chemistry 71(1) (1993) 125-134
A series of di- and trisaccharide glycosides based on the α-L-Rha(1→3)β-D-GlcNAc and α-L-Rha(1→3)α-L-Rha(1→3)β-D-GlcNAc elements have been synthesized to locate the minimal oligosaccharide determinant of the Shigella flexneri O-polysaccharide, which is built from a tetrasaccharide repeating unit, [→2)α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1-]n. These compounds also serve to identify the carbohydrate surface of the Shigella antigen that interacts with a monoclonal antibody, currently the subject of crystallographic studies. Two strategies utilizing suitably protected glycals 1 and 19 were employed to obtain analogs bearing either terminal or glycosylated 2,6-dideoxy-α-L-arabino-hexopyranosyl (2-deoxy-α-L-rhamnopyranosyl) residues. N-Iodosuccinimide activation of the glycals in the presence of selectively protected mono- and disaccharide alcohols afforded 2-deoxy-2-iodo-α-L-rhamnopyranosides and these were ultimately reduced during deprotection stages to afford the desired functionality. Di-O-acetyl L-rhamnal 1 reacted with monosaccharides 2 and 7, and with disaccharide 11, to yield disaccharides 4 and 8, and trisaccharide 12, each bearing a terminal 2-deoxy-α-L-rhamnopyranosyl residue. The selectively protected 3-O-benzoyl-4-O-benzyl-L-rhamnal 19 was synthesized from L-rhamnal and used to prepared trisaccharide 22, which contained an internal 2-deoxy-2-iodo-α-L-rhamnopyranosyl unit. Removal of protecting groups gave the oligosaccharides 6, 10, 14, and 23. Oligosaccharides that contained a 2-deoxy-α-L-rhamnopyranosyl residue showed enhanced inhibitory power: in the case of trisaccharide 23 a 1.8 kcal/mol relative increase in free energy of binding compared to a larger pentasaccharide epitope, α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1→2)α-L-Rhap-1→OMe. These data suggest that the rhamnose O-2 hydroxyl of residue C points toward and has important interactions with binding site amino acids.
synthesis, Shigella flexneri, monoclonal antibodies, O-polysaccharide, binding site, antigen-antibody interaction, 2-deoxy-L-rhamnose
Publication DOI: 10.1139/v93-018Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6 Canada
Methods: 13C NMR, 1H NMR, TLC, ELISA, chemical methods, serological methods
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12. Compound ID: 8277
Structure type: oligomer
Trivial name: disaccharide epitope
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 3621
Hanna HR, Bundle DR "Antibody-oligosaccharide interactions: the synthesis of 2-deoxy-a-L-rhamnose containing oligosaccharide haptens relataed to Shigella flexneri variant Y antigen" -
Canadian Journal of Chemistry 71(1) (1993) 125-134
A series of di- and trisaccharide glycosides based on the α-L-Rha(1→3)β-D-GlcNAc and α-L-Rha(1→3)α-L-Rha(1→3)β-D-GlcNAc elements have been synthesized to locate the minimal oligosaccharide determinant of the Shigella flexneri O-polysaccharide, which is built from a tetrasaccharide repeating unit, [→2)α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1-]n. These compounds also serve to identify the carbohydrate surface of the Shigella antigen that interacts with a monoclonal antibody, currently the subject of crystallographic studies. Two strategies utilizing suitably protected glycals 1 and 19 were employed to obtain analogs bearing either terminal or glycosylated 2,6-dideoxy-α-L-arabino-hexopyranosyl (2-deoxy-α-L-rhamnopyranosyl) residues. N-Iodosuccinimide activation of the glycals in the presence of selectively protected mono- and disaccharide alcohols afforded 2-deoxy-2-iodo-α-L-rhamnopyranosides and these were ultimately reduced during deprotection stages to afford the desired functionality. Di-O-acetyl L-rhamnal 1 reacted with monosaccharides 2 and 7, and with disaccharide 11, to yield disaccharides 4 and 8, and trisaccharide 12, each bearing a terminal 2-deoxy-α-L-rhamnopyranosyl residue. The selectively protected 3-O-benzoyl-4-O-benzyl-L-rhamnal 19 was synthesized from L-rhamnal and used to prepared trisaccharide 22, which contained an internal 2-deoxy-2-iodo-α-L-rhamnopyranosyl unit. Removal of protecting groups gave the oligosaccharides 6, 10, 14, and 23. Oligosaccharides that contained a 2-deoxy-α-L-rhamnopyranosyl residue showed enhanced inhibitory power: in the case of trisaccharide 23 a 1.8 kcal/mol relative increase in free energy of binding compared to a larger pentasaccharide epitope, α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1→2)α-L-Rhap-1→OMe. These data suggest that the rhamnose O-2 hydroxyl of residue C points toward and has important interactions with binding site amino acids.
synthesis, Shigella flexneri, monoclonal antibodies, O-polysaccharide, binding site, antigen-antibody interaction, 2-deoxy-L-rhamnose
Publication DOI: 10.1139/v93-018Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6 Canada
Methods: 13C NMR, 1H NMR, TLC, ELISA, chemical methods, serological methods
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13. Compound ID: 8278
Structure type: oligomer
Trivial name: disaccharide inhibitor
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 3621
Hanna HR, Bundle DR "Antibody-oligosaccharide interactions: the synthesis of 2-deoxy-a-L-rhamnose containing oligosaccharide haptens relataed to Shigella flexneri variant Y antigen" -
Canadian Journal of Chemistry 71(1) (1993) 125-134
A series of di- and trisaccharide glycosides based on the α-L-Rha(1→3)β-D-GlcNAc and α-L-Rha(1→3)α-L-Rha(1→3)β-D-GlcNAc elements have been synthesized to locate the minimal oligosaccharide determinant of the Shigella flexneri O-polysaccharide, which is built from a tetrasaccharide repeating unit, [→2)α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1-]n. These compounds also serve to identify the carbohydrate surface of the Shigella antigen that interacts with a monoclonal antibody, currently the subject of crystallographic studies. Two strategies utilizing suitably protected glycals 1 and 19 were employed to obtain analogs bearing either terminal or glycosylated 2,6-dideoxy-α-L-arabino-hexopyranosyl (2-deoxy-α-L-rhamnopyranosyl) residues. N-Iodosuccinimide activation of the glycals in the presence of selectively protected mono- and disaccharide alcohols afforded 2-deoxy-2-iodo-α-L-rhamnopyranosides and these were ultimately reduced during deprotection stages to afford the desired functionality. Di-O-acetyl L-rhamnal 1 reacted with monosaccharides 2 and 7, and with disaccharide 11, to yield disaccharides 4 and 8, and trisaccharide 12, each bearing a terminal 2-deoxy-α-L-rhamnopyranosyl residue. The selectively protected 3-O-benzoyl-4-O-benzyl-L-rhamnal 19 was synthesized from L-rhamnal and used to prepared trisaccharide 22, which contained an internal 2-deoxy-2-iodo-α-L-rhamnopyranosyl unit. Removal of protecting groups gave the oligosaccharides 6, 10, 14, and 23. Oligosaccharides that contained a 2-deoxy-α-L-rhamnopyranosyl residue showed enhanced inhibitory power: in the case of trisaccharide 23 a 1.8 kcal/mol relative increase in free energy of binding compared to a larger pentasaccharide epitope, α-L-Rhap(1→2)α-L-Rhap(1→3)α-L-Rhap(1→3)β-D-GlcNAcp(1→2)α-L-Rhap-1→OMe. These data suggest that the rhamnose O-2 hydroxyl of residue C points toward and has important interactions with binding site amino acids.
synthesis, Shigella flexneri, monoclonal antibodies, O-polysaccharide, binding site, antigen-antibody interaction, 2-deoxy-L-rhamnose
Publication DOI: 10.1139/v93-018Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6 Canada
Methods: 13C NMR, 1H NMR, TLC, ELISA, chemical methods, serological methods
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14. Compound ID: 13293
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b-D-Olip-(1-4)-b-Rhop-(1-4)-a-L-Rhap-(1-13)-Subst
Subst = SMILES CC[C@@H](C)[C@@H](O)[C@@H]1O[C@H]1C[C@H](C)/C=C/C=C(C)\c2cc(O)c4c(c2)oc3ccc(CC[C@@H](C){13}CO)c(O)c34 |
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Structure type: oligomer
Trivial name: fulicineroside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 5261
Zhou ZY, Liu JK "Pigments of fungi (macromycetes)" -
Natural Product Reports 27(11) (2010) 1531-1570
This review surveys the chemical, biological and mycological literature dealing with the isolation, structure elucidation, biological activities, and synthesis of pigments manufactured by those fungi that produce conspicuous fruiting bodies (macromycetes).
pigment
NCBI PubMed ID: 20694228Publication DOI: 10.1039/c004593dJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
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15. Compound ID: 13482
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b-D-Olip-(1-4)-a-Rhop-(1-4)-b-D-1dOlip-(1C-9)-Subst-(12-1)-a-Rhop
Subst = urdamycinone E aglycon = SMILES O=C1C2=C(C=C(SC)[C@@](C[C@](O)(C)C3)(O){12}[C@]2(O)C3=O)C(C4=C(O){9}C=CC=C41)=O |
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Structure type: oligomer
Trivial name: urdamycin E
Compound class: C-glycoside
The structure is contained in the following publication(s):
- Article ID: 5352
Supong K, Thawai C, Suwanborirux K, Choowong W, Supothina S, Pittayakhajonwut P "Antimalarial and antitubercular C-glycosylated benz[α]anthraquinones from the marine-derived Streptomyces sp. BCC45596" -
Phytochemistry Letters 5(3) (2012) 651-656
Three naturally new C-glycosylated benz[α]anthraquinone derivatives, urdamycinone E (1), urdamycinone G (2), dehydroxyaquayamycin (3) have been isolated from the marine Streptomycetes sp. BCC45596. Urdamycin E (4), the possible biosynthetic precursor of 1-3, has also been identified after a re-cultivation of the strain. These compounds (1-4) exhibited potent anti-Plasmodium palcifarum K1 strain with IC50 values in a range of 0.0534-2.93 μg/mL and anti-Mycobacterium tuberculosis with minimum inhibition concentrations (MICs) in a range of 3.13-12.50 μg/mL. Cytotoxicity against KB, MCF-7, NCI-H187, and Vero cells was also evaluated.
Streptomyces, benz[α]anthraquinones, urdamycinone, dehydroxyaquayamycin, antimalarial, anti-TB
Publication DOI: 10.1016/j.phytol.2012.06.015Journal NLM ID: 101513432Publisher: Amsterdam: Elsevier
Correspondence: Pittayakhajonwut P
Institutions: Department of Biology, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok, Thailand, Center for Bioactive Natural Products from Marine Organisms and Endophytic fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand, National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Klong Luang, Thailand
Methods: 13C NMR, 1H NMR, NMR-2D, IR, ESI-MS, biological assays, HPLC, UV, extraction, optical rotation measurement, CD, CC, cell growth, HR-ESI-MS
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