Found 59 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
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1. Compound ID: 840
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a-L-Fucp-(1-3)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-D-GlcNAc
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S-6)-+ |
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Structure type: oligomer
Trivial name: 6-sulfo-sialyl-LeX
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_141586,IEDB_141794,IEDB_141807,IEDB_142354,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_146100,IEDB_149174,IEDB_149557,IEDB_150092,IEDB_150933,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_241119,IEDB_241120,IEDB_241127,IEDB_423120,IEDB_461720,SB_115,SB_116,SB_128,SB_129,SB_131,SB_157,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 230
Feizi T "Progress in deciphering the information content of the 'glycome' - a crescendo in the closing years of the millennium" -
Glycoconjugate Journal 17(7-9) (2000) 553-565
The closing years of the second millennium have been uplifting for carbohydrate biology. Optimism that oligosaccharide sequences are bearers of crucial biological information has been borne out by the constellation of efforts of carbohydrate chemists, biochemists, immunochemists, and cell- and molecular biologists. The direct involvement of specific oligosaccharide sequences in protein targeting and folding, and in mechanisms of infection, inflammation and immunity is now unquestioned. With the emergence of families of proteins with carbohydrate-binding activities, assignments of information content for defined oligosaccharide sequences will become more common, but the pinpointing and elucidation of the bioactive domains on oligosaccharides will continue to pose challenges even to the most experienced carbohydrate biologists. The neoglycolipid technology incorporates some of the key requirements for this challenge: namely the resolution of complex glycan mixtures, and ligand binding coupled with sequence determination by mass spectrometry.
monoclonal antibodies, mass spectrometry, blood group antigen, carbohydrate ligands, differentiation antigens, embryonic development, galectins, inflammation, leukocyte adhesion, neoglycolipids, oligosaccharide ligands, oligosaccharid probes, selectins
NCBI PubMed ID: 11421348Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: t.feizi@ic.ac.uk
Institutions: The Glycosciences Laboratory, Imperial College School of Medicine, Harrow, United Kingdom
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2. Compound ID: 841
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a-L-Fucp-(1-3)-+
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S-6)-+ |
| |
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-D-GlcNAc
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S-6)-+ |
Show graphically |
Structure type: oligomer
Trivial name: 6,6'-sulfo-sialyl-LeX
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_141586,IEDB_141794,IEDB_141807,IEDB_142354,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_146100,IEDB_149174,IEDB_149557,IEDB_150092,IEDB_150933,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_241119,IEDB_241120,IEDB_241127,IEDB_423120,IEDB_461720,SB_115,SB_116,SB_128,SB_129,SB_131,SB_157,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 230
Feizi T "Progress in deciphering the information content of the 'glycome' - a crescendo in the closing years of the millennium" -
Glycoconjugate Journal 17(7-9) (2000) 553-565
The closing years of the second millennium have been uplifting for carbohydrate biology. Optimism that oligosaccharide sequences are bearers of crucial biological information has been borne out by the constellation of efforts of carbohydrate chemists, biochemists, immunochemists, and cell- and molecular biologists. The direct involvement of specific oligosaccharide sequences in protein targeting and folding, and in mechanisms of infection, inflammation and immunity is now unquestioned. With the emergence of families of proteins with carbohydrate-binding activities, assignments of information content for defined oligosaccharide sequences will become more common, but the pinpointing and elucidation of the bioactive domains on oligosaccharides will continue to pose challenges even to the most experienced carbohydrate biologists. The neoglycolipid technology incorporates some of the key requirements for this challenge: namely the resolution of complex glycan mixtures, and ligand binding coupled with sequence determination by mass spectrometry.
monoclonal antibodies, mass spectrometry, blood group antigen, carbohydrate ligands, differentiation antigens, embryonic development, galectins, inflammation, leukocyte adhesion, neoglycolipids, oligosaccharide ligands, oligosaccharid probes, selectins
NCBI PubMed ID: 11421348Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: t.feizi@ic.ac.uk
Institutions: The Glycosciences Laboratory, Imperial College School of Medicine, Harrow, United Kingdom
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3. Compound ID: 4343
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S-6)-+
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S-6)-+ S-2)-+ | S-2)-+ S-2)-+
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-4)-a-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-4)-a-D-GlcpN-(1-4)-a-L-IdopA-(1-4)-a-D-GlcpN-(1-
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S-3)-+ S-6)-+ |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_241120,IEDB_241121,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 1629
Lindahl U, Li JP, Kusche-Gullberg M, Salmivirta M, Alaranta S, Veromaa T, Emeis J, Roberts I, Taylor C, Oreste P, Zoppetti G, Naggi A, Torri G, Casu B "Generation of 'neoheparin' from E. coli K5 capsular polysaccharide" -
Journal of Medicinal Chemistry 48(2) (2005) 349-352
Heparin remains a major drug in prevention of thromboembolic disease. Concerns related to its animal source have prompted search for heparin analogues. The anticoagulant activity of heparin depends on a specific pentasaccharide sequence that binds antithrombin. We report the generation of a product with antithrombin-binding, anticoagulant, and antithrombotic properties similar to those of heparin, through combined chemical and enzymatic modification of a bacterial (E. coli K5) polysaccharide. The process is readily applicable to large-scale production.
capsular polysaccharide, Escherichia coli, heparin, chemical synthesis, anticoagulant activity, enzymatic modification
NCBI PubMed ID: 15658847Journal NLM ID: 9716531Publisher: Washington, DC: American Chemical Society
Correspondence: ulf.lindahl@imbim.uu.se
Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Box 582, SE-751 23 Uppsala, Sweden
Methods: biological assays, biosynthetic modifications, chemoenzymatic modifications
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4. Compound ID: 5702
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S-6)-+
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LIP-(1-2)-b-D-GlcpN6Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
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Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2494
Darvill A, Augur C, Bergmann C, Carlson RW, Cheong JJ, Eberhard S, Hahn MG, Lo VM, Marfa V, Meyer B, Mohnen D, O'Neill MA, Spiro MD, van Halbeek H, York WS, Albersheim P "Oligosaccharins-oligosaccharides that regulate growth, development and defence responses in plant" -
Glycobiology 2 (1992) 181-198
NCBI PubMed ID: 1498416Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
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5. Compound ID: 5703
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S-6)-+
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LIP-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2494
Darvill A, Augur C, Bergmann C, Carlson RW, Cheong JJ, Eberhard S, Hahn MG, Lo VM, Marfa V, Meyer B, Mohnen D, O'Neill MA, Spiro MD, van Halbeek H, York WS, Albersheim P "Oligosaccharins-oligosaccharides that regulate growth, development and defence responses in plant" -
Glycobiology 2 (1992) 181-198
NCBI PubMed ID: 1498416Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
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6. Compound ID: 5704
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S-6)-+
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LIP-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-V(S)
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2494
Darvill A, Augur C, Bergmann C, Carlson RW, Cheong JJ, Eberhard S, Hahn MG, Lo VM, Marfa V, Meyer B, Mohnen D, O'Neill MA, Spiro MD, van Halbeek H, York WS, Albersheim P "Oligosaccharins-oligosaccharides that regulate growth, development and defence responses in plant" -
Glycobiology 2 (1992) 181-198
NCBI PubMed ID: 1498416Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
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7. Compound ID: 6337
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S-6)-+
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Vac-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc |
Show graphically |
Structure type: oligomer
Compound class: LOS, glycolipid
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2857
Lerouge P "Symbiotic host specificity between leguminous plants and rhizobia is determined by substituted and acylated glucosamine oligosaccharide signals" -
Glycobiology 4 (1994) 127-134
Rhizobia are nitrogen-fixing bacteria which invade root hairs of leguminous plants and induce, in a specific manner, the formation of root nodules in which they fix nitrogen. The early steps of the symbiosis can be considered as a reciprocal molecular communication between the two partners. Initially, the plant excretes a gene inducer which stimulates the expression of bacterial nodulation genes. These nodulation genes are responsible for the synthesis of extracellular host-specific signals, called nodulation factors. The bacterial nodulation factors were isolated and structurally identified as substituted and N-acylated chitin oligosaccharides. These prokaryotic lipo-oligosaccharide signals play a key role in the symbiosis by controlling the host specificity of the bacteria. They constitute a new class of signalling molecules able to elicit nodule organogenesis in leguminous plants in the absence of bacteria.
symbiosis, nodulation factor, nodule organogenesis, plant-microbe interaction, plant-microbe interactions
NCBI PubMed ID: 8054712Publication DOI: 10.1093/glycob/4.2.127Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Centre Régional de Spectroscopie, URA-CNRS 464, Université de Rouen, Mont Saint Aignan, France
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, GC, CAD-MIKE-MS
- Article ID: 3050
Carlson RW, Price NPJ, Stacey G "The biosynthesis of rhizobial lipo-oligosaccharide nodulation signal molecules" -
Molecular Plant-Microbe Interactions 7 (1994) 684-695
While a great deal has been learned concerning the biosynthesis of Nod factors, there is much that remains to be determined. The functions of many Nod proteins involved in adding the host-specific modifications to the Nod factors remain to be unequivocally identified. Some of the genes required for these modifications have not yet been isolated, e.g., those involved in carbamylation, or addition of D-Ara. Additionally the cellular location of most of the Nod proteins and, concomitantly, the modifications they determine are not known. The actual in vivo substrates for the NodABC proteins have not been identified, and the enzyme activities of purified NodA and NodC have not been demonstrated. The synthesis and export of the Nod factors most probably involves some type of carrier/anchor which remains unidentified. Analysis of GlcNAc metabolites from various mutants, e.g., nodA-, nodB-, or nodC- mutants, should facilitate the identification of the in vivo substrates involved in the synthesis of the "common" Nod factor and, thereby, lead to a greater understanding of Nod factor biosynthesis and transport. Finally, comparison of Nod factor biosynthesis to other examples of polysaccharide or glycolipid biosynthetic pathways suggest that several key enzymes remain to be identified. It is hoped that this discussion will be helpful in designing strategies for the detection and isolation of such novel enzymes.
NCBI PubMed ID: 7873777Journal NLM ID: 9107902Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
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8. Compound ID: 6621
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S-6)-+
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C16={t2,c9}-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc |
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Structure type: oligomer
Trivial name: NodRm-V(S), NodRm-IV(S)
Compound class: glucan, chitin glycolipid, polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2857
Lerouge P "Symbiotic host specificity between leguminous plants and rhizobia is determined by substituted and acylated glucosamine oligosaccharide signals" -
Glycobiology 4 (1994) 127-134
Rhizobia are nitrogen-fixing bacteria which invade root hairs of leguminous plants and induce, in a specific manner, the formation of root nodules in which they fix nitrogen. The early steps of the symbiosis can be considered as a reciprocal molecular communication between the two partners. Initially, the plant excretes a gene inducer which stimulates the expression of bacterial nodulation genes. These nodulation genes are responsible for the synthesis of extracellular host-specific signals, called nodulation factors. The bacterial nodulation factors were isolated and structurally identified as substituted and N-acylated chitin oligosaccharides. These prokaryotic lipo-oligosaccharide signals play a key role in the symbiosis by controlling the host specificity of the bacteria. They constitute a new class of signalling molecules able to elicit nodule organogenesis in leguminous plants in the absence of bacteria.
symbiosis, nodulation factor, nodule organogenesis, plant-microbe interaction, plant-microbe interactions
NCBI PubMed ID: 8054712Publication DOI: 10.1093/glycob/4.2.127Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Centre Régional de Spectroscopie, URA-CNRS 464, Université de Rouen, Mont Saint Aignan, France
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, GC, CAD-MIKE-MS
- Article ID: 5625
Lerouge P, Roche P, Faucher C, Maillet F, Truchet G, Promé JC, Dénarié J "Symbiotic host-specificity of Rhizobium meliloti is determined by a sulphated and acylated glucosamine oligosaccharide signal" -
Nature 344(6268) (1990) 781-784
Rhizobia are symbiotic bacteria that elicit the formation on leguminous plants of specialized organs, root nodules, in which they fix nitrogen. In various Rhizobium species, such as R. leguminosarum and R. meliloti, common and host-specific nodulation (nod) genes have been identified which determine infection and nodulation of specific hosts. Common nodABC genes as well as host-specific nodH and nodQ genes were shown recently, using bioassays, to be involved in the production of extracellular Nod signals. Using R. meliloti strains overproducing symbiotic Nod factors, we have purified the major alfalfa-specific signal, NodRm-1, by gel permeation, ion exchange and C18 reverse-phase high performance liquid chromatography. From mass spectrometry, nuclear magnetic resonance, (35)S-labelling and chemical modification studies, NodRm-1 was shown to be a sulphated β-1,4-tetrasaccharide of D-glucosamine (Mr 1102) in which three amino groups were acetylated and one was acylated with a C16 bis-unsaturated fatty acid. This purified Nod signal specifically elicited root hair deformation on the homologous host when added in nanomolar concentration
Rhizobium meliloti, Glucosamine, alfalfa
NCBI PubMed ID: 2330031Publication DOI: 10.1038/344781a0Journal NLM ID: 0410462Publisher: Basingstoke: Nature Publishing Group
Institutions: Centre de Recherches de Biochimie et de Génétique Cellulaire, CNRS LP8201, Toulouse, France, Laboratorie de Biologie Moléculaire des Relations Plantes-Microorganismes, CNRS-INRA, Castanet-Tolosan, France
Methods: 13C NMR, 1H NMR, DNA techniques, biological assays, MS, radiolabeling, HPLC, UV, ion-exchange chromatography, extraction, methylation analysis, gel permeation chromatography, derivatization
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9. Compound ID: 6622
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S-6)-+
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C16={t2,c9}-(1-2)-b-D-GlcpN6Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(S,Ac), NodRm-V(S,Ac)
Compound class: chitin glycolipid
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2857
Lerouge P "Symbiotic host specificity between leguminous plants and rhizobia is determined by substituted and acylated glucosamine oligosaccharide signals" -
Glycobiology 4 (1994) 127-134
Rhizobia are nitrogen-fixing bacteria which invade root hairs of leguminous plants and induce, in a specific manner, the formation of root nodules in which they fix nitrogen. The early steps of the symbiosis can be considered as a reciprocal molecular communication between the two partners. Initially, the plant excretes a gene inducer which stimulates the expression of bacterial nodulation genes. These nodulation genes are responsible for the synthesis of extracellular host-specific signals, called nodulation factors. The bacterial nodulation factors were isolated and structurally identified as substituted and N-acylated chitin oligosaccharides. These prokaryotic lipo-oligosaccharide signals play a key role in the symbiosis by controlling the host specificity of the bacteria. They constitute a new class of signalling molecules able to elicit nodule organogenesis in leguminous plants in the absence of bacteria.
symbiosis, nodulation factor, nodule organogenesis, plant-microbe interaction, plant-microbe interactions
NCBI PubMed ID: 8054712Publication DOI: 10.1093/glycob/4.2.127Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Centre Régional de Spectroscopie, URA-CNRS 464, Université de Rouen, Mont Saint Aignan, France
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, GC, CAD-MIKE-MS
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10. Compound ID: 6623
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?%S-6)-+
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cVac-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: chitin glycolipid
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 2857
Lerouge P "Symbiotic host specificity between leguminous plants and rhizobia is determined by substituted and acylated glucosamine oligosaccharide signals" -
Glycobiology 4 (1994) 127-134
Rhizobia are nitrogen-fixing bacteria which invade root hairs of leguminous plants and induce, in a specific manner, the formation of root nodules in which they fix nitrogen. The early steps of the symbiosis can be considered as a reciprocal molecular communication between the two partners. Initially, the plant excretes a gene inducer which stimulates the expression of bacterial nodulation genes. These nodulation genes are responsible for the synthesis of extracellular host-specific signals, called nodulation factors. The bacterial nodulation factors were isolated and structurally identified as substituted and N-acylated chitin oligosaccharides. These prokaryotic lipo-oligosaccharide signals play a key role in the symbiosis by controlling the host specificity of the bacteria. They constitute a new class of signalling molecules able to elicit nodule organogenesis in leguminous plants in the absence of bacteria.
symbiosis, nodulation factor, nodule organogenesis, plant-microbe interaction, plant-microbe interactions
NCBI PubMed ID: 8054712Publication DOI: 10.1093/glycob/4.2.127Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Centre Régional de Spectroscopie, URA-CNRS 464, Université de Rouen, Mont Saint Aignan, France
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, GC, CAD-MIKE-MS
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11. Compound ID: 6730
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S-6)-+
|
Pam-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(C16:2,S), NodRm-IV(S), n=2, NodRm-V(S), n=3
Compound class: LOS, chitin glycolipid
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141181,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3050
Carlson RW, Price NPJ, Stacey G "The biosynthesis of rhizobial lipo-oligosaccharide nodulation signal molecules" -
Molecular Plant-Microbe Interactions 7 (1994) 684-695
While a great deal has been learned concerning the biosynthesis of Nod factors, there is much that remains to be determined. The functions of many Nod proteins involved in adding the host-specific modifications to the Nod factors remain to be unequivocally identified. Some of the genes required for these modifications have not yet been isolated, e.g., those involved in carbamylation, or addition of D-Ara. Additionally the cellular location of most of the Nod proteins and, concomitantly, the modifications they determine are not known. The actual in vivo substrates for the NodABC proteins have not been identified, and the enzyme activities of purified NodA and NodC have not been demonstrated. The synthesis and export of the Nod factors most probably involves some type of carrier/anchor which remains unidentified. Analysis of GlcNAc metabolites from various mutants, e.g., nodA-, nodB-, or nodC- mutants, should facilitate the identification of the in vivo substrates involved in the synthesis of the "common" Nod factor and, thereby, lead to a greater understanding of Nod factor biosynthesis and transport. Finally, comparison of Nod factor biosynthesis to other examples of polysaccharide or glycolipid biosynthetic pathways suggest that several key enzymes remain to be identified. It is hoped that this discussion will be helpful in designing strategies for the detection and isolation of such novel enzymes.
NCBI PubMed ID: 7873777Journal NLM ID: 9107902Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
- Article ID: 4176
Staehelin C, Schultze M, Kondorosi E, Mellor RB, Boller T, Kondorosi A "Structural modifications in Rhizobium meliloti Nod factors influence their stability against hydrolysis by root chitinases" -
Plant Journal: for Cell and Molecular Biology 5 (1994) 319-330
Acylated chitooligosaccharide signals (Nod factors) trigger the development of root nodules on leguminous plants and play an important role in determining host specificity in the Rhizobium-plant symbiosis. Here, the ability of plant chitinases to hydrolyze different Nod factors and the potential significance of the structural modifications of Nod factors in stabilizing them against enzymatic inactivation were investigated. Incubation of the sulfated Nod factors of Rhizobium meliloti, NodRm-IV(S) and NodRm-V(S), as well as their desulfated derivatives NodRm-IV and NodRm-V, with purified chitinases from the roots of the host plant Medicago and the nonhost plant Vicia resulted in the release of the acylated lipotrisaccharide NodRm-III from NodRm-V, NodRm-IV and NodRm-V(S), whereas NodRm-IV(S) was completely resistant to digestion by both chitinases. Kinetic analysis showed that the structural parameters determining host specificity, the length of the oligosaccharide chain, the acylation at the nonreducing end and the sulfatation at the reducing end of the lipooligosaccharide, influence the stability of the molecule against degradation by chitinases. When the Nod factors were incubated in the presence of intact roots of Medicago, as well as of Vicia, the acylated lipotrisaccharide was similarly released in vivo from all Nod factors except NodRm-IV(S). In addition, a dimer-forming activity was observed in intact roots which also cleaved NodRm-IV(S). This activity was much greater in Medicago than in Vicia and increased upon incubation. The initial overall degradation rate of the Nod factors on Medicago was inversely correlated with their biological activities on Medicago roots. These results open the possibility that the activity of Nod factors on Medicago may partly be determined by the action of chitinases.
Publication DOI: 10.1111/j.1365-313X.1994.00319.xJournal NLM ID: 9207397Publisher: Oxford: Blackwell Scientific Publishers and BIOS Scientific Publishers for the Society for Experimental Biology
Institutions: Institut des Sciences Végétales, CNRS, Gif-sur-Yvette, France, Institute of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, Hungary, Botanisches lnstitut der Universität Basel, Basel, Switzerland
Methods: FAB-MS, SDS-PAGE, TLC, enzymatic hydrolysis
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12. Compound ID: 6739
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S-6)-+
|
LIP-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: chitin glycolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3060
Vijn I, Das Neves L, van Kammen A, Franssen H, Bisseling T "Nod factors and nodulation in plants" -
Science 260 (1993) 1764-1765
NCBI PubMed ID: 8511583Journal NLM ID: 0404511Publisher: Washington, DC: American Association for the Advancement of Science
Institutions: Department of Molecular Biology, Agricultural University, Dreijenlaan, Wageningen, The Netherlands
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13. Compound ID: 6756
|
S-6)-+
|
/Variants 0/-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc
/Variants 0/ is:
C16={?,?}-(1-2)-
OR (exclusively)
C16={?,?,?}-(1-2)- |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3064
Spaink HP "The molecular basis of the host specificity of the Rhizobium bacteria" -
Antonie van Leeuwenhoek 65 (1994) 81-98
The interaction between soil bacteria belonging to the genera Rhizobium, Bradyrhizobium and Azorhizobium and leguminous plants results in the induction of a new plant organ, the root nodule. After invading these root nodules via infection threads the bacteria start to fix atmospheric nitrogen into ammonia which is beneficial for the host plant. This symbiotic interaction is highly host-specific in that each rhizobial strain is able to associate with only a limited number of host plant species. The subject of this presentation is the molecular mechanism by which the bacterium determines its host-specific characteristics. This mechanism appears to be based on at least two stages of molecular signaling between the bacterium and the plant host. In the first stage, flavonoids secreted by the plant root induce, in a host specific way, the transcription of bacterial genes which are involved in nodulation, the so-called nod genes. This leads to the second step of the signaling system: the production and secretion of lipo-oligosaccharide molecules by the Rhizobium bacteria. These signal molecules, which are acylated forms of small fragments of chitin, have various discernable effects on the roots of the host plants. One of these effects is the dedifferentiation of groups of cells located in the cortex which leads to the formation of nodule meristems. In their mitogenic activity the bacterial signals resemble several well-known plant hormones like auxins and cytokinins. However, there are two major differences: (i) the bacterial signals lead to the induction of a specific organ and (ii) they are host-specific in that only the signals produced by compatible bacteria are able to induce meristems. The nod genes determine this stage of host specificity by their essential role in the biosynthesis of the signal molecules. They appear to encode enzymes which are involved in the processes of fatty acid biosynthesis, fatty acid transfer, chitin synthesis and chitin modification. I will illustrate the statement that the nod gene products are ideal model enzymes for the study of these important processes because they are not needed in the free-living state of the bacteria.
symbiosis, plant-microbe interaction, nodulation genes, signal molecules
NCBI PubMed ID: 7718036Publication DOI: 10.1007/BF00871750Journal NLM ID: 0372625Publisher: Dordrecht: Kluwer Academic
Institutions: Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University, Leiden, The Netherlands
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14. Compound ID: 6757
|
S-6)-+
|
C16={?,?}-(1-2)-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3064
Spaink HP "The molecular basis of the host specificity of the Rhizobium bacteria" -
Antonie van Leeuwenhoek 65 (1994) 81-98
The interaction between soil bacteria belonging to the genera Rhizobium, Bradyrhizobium and Azorhizobium and leguminous plants results in the induction of a new plant organ, the root nodule. After invading these root nodules via infection threads the bacteria start to fix atmospheric nitrogen into ammonia which is beneficial for the host plant. This symbiotic interaction is highly host-specific in that each rhizobial strain is able to associate with only a limited number of host plant species. The subject of this presentation is the molecular mechanism by which the bacterium determines its host-specific characteristics. This mechanism appears to be based on at least two stages of molecular signaling between the bacterium and the plant host. In the first stage, flavonoids secreted by the plant root induce, in a host specific way, the transcription of bacterial genes which are involved in nodulation, the so-called nod genes. This leads to the second step of the signaling system: the production and secretion of lipo-oligosaccharide molecules by the Rhizobium bacteria. These signal molecules, which are acylated forms of small fragments of chitin, have various discernable effects on the roots of the host plants. One of these effects is the dedifferentiation of groups of cells located in the cortex which leads to the formation of nodule meristems. In their mitogenic activity the bacterial signals resemble several well-known plant hormones like auxins and cytokinins. However, there are two major differences: (i) the bacterial signals lead to the induction of a specific organ and (ii) they are host-specific in that only the signals produced by compatible bacteria are able to induce meristems. The nod genes determine this stage of host specificity by their essential role in the biosynthesis of the signal molecules. They appear to encode enzymes which are involved in the processes of fatty acid biosynthesis, fatty acid transfer, chitin synthesis and chitin modification. I will illustrate the statement that the nod gene products are ideal model enzymes for the study of these important processes because they are not needed in the free-living state of the bacteria.
symbiosis, plant-microbe interaction, nodulation genes, signal molecules
NCBI PubMed ID: 7718036Publication DOI: 10.1007/BF00871750Journal NLM ID: 0372625Publisher: Dordrecht: Kluwer Academic
Institutions: Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University, Leiden, The Netherlands
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15. Compound ID: 6766
|
?%S-6)-+
|
Vac-(1-2)-b-D-GlcpNMe-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc |
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Structure type: oligomer
Trivial name: chitin glycolipid
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3067
Poupot R, Martinez-Romero E, Promé JC "Nodulation factors from Rhizobium tropici are sulfated or nonsulfated chitopentasaccharides containing an N-methyl-N-acylglucosaminyl terminus" -
Biochemistry 32(39) (1993) 10430-10435
Phaseolus vulgaris (common bean) can be nodulated by several Rhizobium species. Among them, Rhizobium tropici has a relatively broad host range, as it is able to infect beans, Leucaena trees, and several other legumes. This work describes the isolation and the characterization of extracellular factors (Nod factors) whose production from R. tropici was triggered by the transcriptional activation of its nod genes. These factors consist of a chitopentaose backbone in which the N-acetyl group of the nonreducing end glucosaminyl residue is replaced by an N-methyl-N-vaccenoyl one. Some of these molecules are sulfated on position 6 of the terminal reducing glucosamine.
NCBI PubMed ID: 8399187Publication DOI: 10.1021/bi00090a019Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
Methods: 1H NMR, FAB-MS, TLC
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Next 15 structure(s)
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