Found 7 structures.
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1. Compound ID: 6626
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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: 2858
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, CID-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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2. Compound ID: 6627
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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 |
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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: 2858
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, CID-MIKE-MS
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3. Compound ID: 6836
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S-6)-+
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/Variants 0/-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc
/Variants 0/ is:
C16={t2,t4,c9}-(1-2)-
OR (exclusively)
C16={t2,c9}-(1-2)- |
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Structure type: oligomer
Trivial name: NodRm
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: 3121
Schultze M, Kondorosi E, Ratet P, Buiré M, Kondorosi A "Cell and molecular biology of Rhizobium - Plant interactions" -
International Review of Cytology 156 (1994) 1-75
This chapter discusses the Cell and molecular biology of Rhizobium-plant interactions. Soil bacteria, referred to as rhizobia belonging to the genera Rhizobium, Bradyrhizobium, and Azorhizobium, have the unique ability to induce nitrogen-fixing nodules on the roots or stems of leguminous plants. Nodule development consists of several stages determined by different sets of genes both in the host and symbiont. At least at the very early steps of symbiosis, the bacterial and plant genes are activated consecutively by signal exchanges between the symbiotic partners. First, flavonoid signal molecules exuded by the host plant root induce the expression of nodulation (nod, nol) genes in Rhizobium in conjunction with the bacterial activator NodD protein. Then, in the second step, lipooligosaccharide Nod factors with various host-specific structural modifications are produced by the bacterial Nod proteins. The Nod factors induce various plant reactions, such as root hair deformation, initiation of nodule meristems, and induction of early nodulin genes, leading to nodule formation. Other classes of bacterial genes are required for successful infection and for nitrogen fixation. This chapter includes only the early events of communication between rhizobia and their host plants, that is, the perception of flavonoid signals by the bacteria, the production of Nod signals by rhizobia, and the early plant responses to the bacteria.
Publication DOI: 10.1016/S0074-7696(08)62252-4Journal NLM ID: 2985180RInstitutions: Institut des Sciences Végétales, CNRS, Gif-sur-Yvette, France, Institute of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, Hungary
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4. Compound ID: 10131
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S-6)-+
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/Variants 0/-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc
/Variants 0/ is:
cdPam-(1-2)-
OR (exclusively)
C16={t2,t4,c9}-(1-2)-
OR (exclusively)
C16={t2,c9}-(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_239236,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 4215
Ardourel M, Demont N, Debellé F, Maillet F, de Billy F, Promé J, Dénarié J, Truchet G "Rhizobium meliloti lipooligosaccharide nodulation factors: Different structural requirements for bacterial entry into target root hair cells and induction of plant symbiotic developmental responses" -
Plant Cell 6 (1994) 1357-1374
Rhizobium meliloti produces lipochitooligosaccharide nodulation NodRm factors that are required for nodulation of legume hosts. NodRm factors are O-acetylated and N-acylated by specific C16-unsaturated fatty acids. nodL mutants produce non-O-acetylated factors, and nodFE mutants produce factors with modified acyl substituents. Both mutants exhibited a significantly reduced capacity to elicit infection thread (IT) formation in alfalfa. However, once initiated, ITs developed and allowed the formation of nitrogen-fixing nodules. In contrast, double nodF/nodL mutants were unable to penetrate into legume hosts and to form ITs. Nevertheless, these mutants induced widespread cell wall tip growth in trichoblasts and other epidermal cells and were also able to elicit cortical cell activation at a distance. NodRm factor structural requirements are thus clearly more stringent for bacterial entry than for the elicitation of developmental plant responses.
NCBI PubMed ID: 7994171Publication DOI: 10.1105/tpc.6.10.1357Journal NLM ID: 9208688Publisher: Rockville, MD: American Society of Plant Physiologists
Institutions: Laboratoire de Biologie Moléculaire des Relations Plantes-Microorganismes, CNRS-INRA, Castanet-Tolosan, France
Methods: GC-MS, LSI-MS, microscopy, plant assays
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5. Compound ID: 13300
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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)-b-D-GlcpNAc |
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Structure type: oligomer
Compound class: lipochitooligosaccharide
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: 5269
Gough C, Cullimore J "Lipo-chitooligosaccharide signaling in endosymbiotic plant-microbe interactions" -
Molecular Plant-Microbe Interactions 24(8) (2011) 867-878
The arbuscular mycorrhizal (AM) and the rhizobia-legume (RL) root endosymbioses are established as a result of signal exchange in which there is mutual recognition of diffusible signals produced by plant and microbial partners. It was discovered 20 years ago that the key symbiotic signals produced by rhizobial bacteria are lipo-chitooligosaccharides (LCO), called Nod factors. These LCO are perceived via lysin-motif (LysM) receptors and activate a signaling pathway called the common symbiotic pathway (CSP), which controls both the RL and the AM symbioses. Recent work has established that an AM fungus, Glomus intraradices, also produces LCO that activate the CSP, leading to induction of gene expression and root branching in Medicago truncatula. These Myc-LCO also stimulate mycorrhization in diverse plants. In addition, work on the nonlegume Parasponia andersonii has shown that a LysM receptor is required for both successful mycorrhization and nodulation. Together these studies show that structurally related signals and the LysM receptor family are key components of both nodulation and mycorrhization. LysM receptors are also involved in the perception of chitooligosaccharides (CO), which are derived from fungal cell walls and elicit defense responses and resistance to pathogens in diverse plants. The discovery of Myc-LCO and a LysM receptor required for the AM symbiosis, therefore, not only raises questions of how legume plants discriminate fungal and bacterial endosymbionts but also, more generally, of how plants discriminate endosymbionts from pathogenic microorganisms using structurally related LCO and CO signals and of how these perception mechanisms have evolved.
lipochitooligosaccharide
NCBI PubMed ID: 21469937Publication DOI: 10.1094/MPMI-01-11-0019Journal NLM ID: 9107902Correspondence: Clare.Gough@toulouse.inra.fr; Julie.Cullimore@toulouse.inra.fr
Institutions: Laboratory of Plant-Microbe Interactions, Institut national de la recherche agronomique, Paris, France
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6. Compound ID: 13553
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S-6)-+
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C16={t2,c9}-(1-2)-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-{{{-b-D-GlcpNAc-(1-4)-}}}/n=1-2/-b-D-GlcpNAc |
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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: 5387
Cullimore J, Gough C "Lipochitooligosaccharide perception and the basis of partner recognition in root endosymbioses" -
Book: Molecular Microbial Ecology of the Rhizosphere (2013) Vol. 1, Chapter 45, 483-494
Root endosymbioses play key roles in plant nutrition in, both, agronomic and natural ecosystems. Of most importance are the arbuscular mycorrhizal (AM) symbiosis, in which the fungus improves the uptake of nutrients by the plant (particularly phosphorus and nitrogen), and secondly the Rhizobium-legume (RL) symbiosis in which Rhizobia bacteria fix dinitrogen allowing legumes to grow independently of a mineral nitrogen source. Although these symbioses seem quite different, studies on legumes have shown that the establishment of the AM and the RL symbioses require a set of common plant genes, constituting the common symbiotic pathway (CSP), thus supporting the hypothesis that the more recent RL symbiosis evolved from the more ancient AM symbiosis.
LOS, bacteria, legume, fungi, Nod-factors, mycorrhizae
Publication DOI: 10.1002/9781118297674.ch45Publisher: Hoboken NJ: Wiley-Blackwell
Editors: de Bruijn FJ
Institutions: Laboratoire des Interactions Plantes-Microorganismes (LIPM), INRA, CNRS, France
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7. Compound ID: 13557
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S-6)-+
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C16={t2,c9}-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpN(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
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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: 5388
Fliegmann J, Canova S, Lachaud C, Uhlenbroich S, Gasciolli V, Pichereaux C, Rossignol M, Rosenberg C, Cumener M, Pitorre D, Lefebvre B, Gough C, Samain E, Fort S, Driguez H, Vauzeilles B, Beau JM, Nurisso A, Imberty A, Cullimore J, Bono JJ "Lipo-chitooligosaccharidic symbiotic signals are recognized by LysM receptor-like kinase LYR3 in the legume Medicago truncatula" -
ACS Chemical Biology 8(9) (2013) 1900-1906
While chitooligosaccharides (COs) derived from fungal chitin are potent elicitors of defense reactions, structurally related signals produced by certain bacteria and fungi, called lipo-chitooligosaccharides (LCOs), play important roles in the establishment of symbioses with plants. Understanding how plants distinguish between friend and foe through the perception of these signals is a major challenge. We report the synthesis of a range of COs and LCOs, including photoactivatable probes, to characterize a membrane protein from the legume Medicago truncatula. By coupling photoaffinity labeling experiments with proteomics and transcriptomics, we identified the likely LCO-binding protein as LYR3, a lysin motif receptor-like kinase (LysM-RLK). LYR3, expressed heterologously, exhibits high-affinity binding to LCOs but not COs. Homology modeling, based on the Arabidopsis CO-binding LysM-RLK AtCERK1, suggests that LYR3 could accommodate the LCO in a conserved binding site. The identification of LYR3 opens up ways for the molecular characterization of LCO/CO discrimination.
LOS, bacteria, legume, fungi, Nod-factors, mycorrhizae
NCBI PubMed ID: 23808871Publication DOI: 10.1021/cb400369uJournal NLM ID: 101282906Publisher: Washington, DC: American Chemical Society
Correspondence: Jean-Jacques.Bono@toulouse.inra.fr
Institutions: INRA, Laboratoire des Interactions Plantes-Microorganismes (LIPM), Castanet-Tolosan, France, CNRS, Laboratoire des Interactions Plantes-Microorganismes (LIPM), Castanet-Tolosan, France, Université Paris-Sud and CNRS, Laboratoire de Synthèse de Biomolécules, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Orsay, France, Université de Toulouse, Laboratoire de Recherche en Sciences Végétales (LRSV), Castanet-Tolosan, France, CNRS, Castanet-Tolosan, France, Plateforme de Protéomique, Toulouse, France, Centre de Recherches sur les Macromolécules Végétales, Grenoble, France, Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, Gif-sur-Yvette,France, School of Pharmaceutical Sciences, Geneva, Switzerland
Methods: SDS-PAGE, radiolabeling, molecular modeling, photoaffinity labeling, autoradiography
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