Show legend Show as text

Structure type: oligomer
Aglycon: Fig. 1
Contained glycoepitopes: IEDB_130646,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_153212,IEDB_190606,IEDB_241099,IEDB_423114,SB_165,SB_166,SB_187,SB_195,SB_30,SB_7,SB_74,SB_85,SB_88

• Article ID: 1372
  Bettler E, Samain E, Chazalet V, Bosso C, Heyraud A, Joziasse DH, Wakarchuk WW, Imberty A, Geremia RA "The living factory: In vivo production of N-acetyllactosamine containing carbohydrates in E-coli" - Glycoconjugate Journal 16(3) (1999) 205-212
  

  Scientific and commercial interest in oligosaccharides is increasing, but their availability is limited as production relies on chemical or chemo-enzymatic synthesis. In search for a more economical, alternative procedure, we have investigated the possibility of producing specific oligosaccharides in E. coli that express the appropriate glycosyltransferases. The Azorhizobium chitin pentaose synthase NodC (a β(1,4)GlcNAc-oligosaccharide synthase), and the Neisseria β(1,4)galactosyltransferase LgtB, were co-expressed in E. coli. The major oligosaccharide isolated from the recombinant strain, was subjected to LC-MS, FAB-MS and NMR analysis, and identified as βGal(1,4)[βGlcNAc(1,4)]4GlcNAc. High cell density culture yielded more than 1.0 gr of the hexasaccharide per liter of culture. The compound was found to be an acceptor in vitro for βGal(1,4)GlcNAc α(1,3)galactosyltransferase, which suggests that the expression of additional glycosyltransferases in E. coli will allow the production of more complex oligosaccharides.

  carbohydrates, carbohydrate, production, N-acetyllactosamine, in vivo, in vivo production

  NCBI PubMed ID: 10596895
  Journal NLM ID: 8603310
  Publisher: Kluwer Academic Publishers
  Correspondence: geremia@cermav.cnrs.fr
  Institutions: Centre de Recherches sur les Macromolecules Vegetales CNRS, Grenoble cedex, France
  Methods: FAB-MS, NMR, LC-MS
  
   
  
  Escherichia coli
  CSDB ID 6257 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit ; n=4-5
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_153212,IEDB_241099,IEDB_423114,IEDB_423150,SB_74,SB_85

• Article ID: 1623
  Kannenberg E, Carlson RW "An abundance of nodulation factors" - Chemistry and Biology 12(9) (2005) 956-958
  

  In this issue of Chemistry and Biology, Moron et al. [1] report that Rhizobium tropici CIAT899 produces different Nod factors in response to flavonoid induction under differing environmental conditions. This unanticipated environmental dependence has implications for altering or potentially improving the host-bacteria interaction in bean nodulation

  chemistry, carbohydrate, Research, complex, factor, response, Rhizobia, Rhizobium, interaction, biology, nodulation, implication, Rhizobium tropici, induction, environmental, dependence, flavonoid, nod, nod factors

  NCBI PubMed ID: 16183018
  Journal NLM ID: 9500160
  Publisher: Maryland Heights, MO: Elsevier
  Institutions: Complex Carbohydrate Research Center, The University of Georgia, Athens, 30602, USA
  Methods: biological assays
  
   
  
  Rhizobium tropici CIAT899
  CSDB ID 10560 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_241099,SB_74,SB_85,SB_86

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Bradyrhizobium japonicum
  CSDB ID 126608 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_241099,SB_74,SB_85,SB_86

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Bradyrhizobium japonicum
  CSDB ID 126609 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_153212,IEDB_241099,SB_74,SB_85

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Rhizobium leguminosarum bv. viciae
  CSDB ID 126610 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_153212,IEDB_241099,SB_74,SB_85

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Rhizobium leguminosarum bv. viciae
  CSDB ID 126611 (all data & tools)

Show legend Show as text

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

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Rhizobium meliloti
  CSDB ID 126612 (all data & tools)

Show legend Show as text

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

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Rhizobium meliloti
  CSDB ID 126613 (all data & tools)

Show legend Show as text

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

• 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: 1498416
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA
  
   
  
  Rhizobium meliloti
  CSDB ID 126614 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1388 [M+H]+
Trivial name: NodBj-V (C16:1, MeFuc)
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_241099,SB_74,SB_85,SB_86

• Article ID: 2668
  Carlson RW, Sanjuan J, Bhat UR, Glushka J, Spaink HP, Wijfjes AHM, Van Brussel AAN, Stokkermans TJW, Peters NK, Stacey G "The structures and biological activities of the lipo-oligosaccharide nodulation signals produced by type I and II strains of Bradyrhizobium japonicum" - Journal of Biological Chemistry 268 (1993) 18372-18381
  

  Bradyrhizobium japonicum produces lipo-oligosaccharide signal molecules that induce deformation of root hairs and meristematic activity on soybeans. B. japonicum USDA135 (a Type I strain) produces modified chitin pentasaccharide molecules with either a terminal N-C16:0- or N-C18:1-glucosamine with and without an O-acetyl group at C-6 and with 2-O-methylfucose linked to C-6 of the reducing N-acetylglucosamine. An additional molecule has N-C16:1-glucosamine and no O-acetyl group. All of these molecules cause root hair deformation on Vicia sativa and Glycine soja. The C18:1-containing molecules were tested and found to induce meristem formation on G. soja. USDA61 (a Type II strain) produces eight additional molecules. Five have a carbamoyl group on the terminal N-acylglucosamine. Six have chitin tetrasaccharide backbones. Three have a terminal N-acyl-N-methylglucosaminosyl residue. In four molecules, the reducing-end N-acetylglucosamine is glycosidically linked to glycerol and has a branching fucosyl, rather than a 2-O-methylfucosyl, residue. One molecule has a terminal N-acylglucosamine that has both acetyl and carbamoyl groups (one each).

  NCBI PubMed ID: 8349712
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, Department of Microbiology and the Center for Legume Research, University of Tennessee, Knoxville, lknnessee 37996, Institute of Molecular Plant Sciences, Leiden University, 2311 VJ Leiden, The Netherlands, Ohio State Biotechnology Center, Ohio State University, Columbus, Ohio 43210
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, TLC, biological assays, composition analysis, NMR-1D
  
   
  
  Bradyrhizobium japonicum USDA135
  CSDB ID 136720 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1416 [M+H]+
Trivial name: NodBj-V(C18:1 MeFuc)
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_187036,IEDB_241099,SB_74,SB_85,SB_86

• Article ID: 2668
  Carlson RW, Sanjuan J, Bhat UR, Glushka J, Spaink HP, Wijfjes AHM, Van Brussel AAN, Stokkermans TJW, Peters NK, Stacey G "The structures and biological activities of the lipo-oligosaccharide nodulation signals produced by type I and II strains of Bradyrhizobium japonicum" - Journal of Biological Chemistry 268 (1993) 18372-18381
  

  Bradyrhizobium japonicum produces lipo-oligosaccharide signal molecules that induce deformation of root hairs and meristematic activity on soybeans. B. japonicum USDA135 (a Type I strain) produces modified chitin pentasaccharide molecules with either a terminal N-C16:0- or N-C18:1-glucosamine with and without an O-acetyl group at C-6 and with 2-O-methylfucose linked to C-6 of the reducing N-acetylglucosamine. An additional molecule has N-C16:1-glucosamine and no O-acetyl group. All of these molecules cause root hair deformation on Vicia sativa and Glycine soja. The C18:1-containing molecules were tested and found to induce meristem formation on G. soja. USDA61 (a Type II strain) produces eight additional molecules. Five have a carbamoyl group on the terminal N-acylglucosamine. Six have chitin tetrasaccharide backbones. Three have a terminal N-acyl-N-methylglucosaminosyl residue. In four molecules, the reducing-end N-acetylglucosamine is glycosidically linked to glycerol and has a branching fucosyl, rather than a 2-O-methylfucosyl, residue. One molecule has a terminal N-acylglucosamine that has both acetyl and carbamoyl groups (one each).

  NCBI PubMed ID: 8349712
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, Department of Microbiology and the Center for Legume Research, University of Tennessee, Knoxville, lknnessee 37996, Institute of Molecular Plant Sciences, Leiden University, 2311 VJ Leiden, The Netherlands, Ohio State Biotechnology Center, Ohio State University, Columbus, Ohio 43210
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, TLC, biological assays, composition analysis, NMR-1D
  
   
  
  Bradyrhizobium japonicum USDA61, Bradyrhizobium japonicum USDA110, Bradyrhizobium japonicum USDA135
  CSDB ID 136721 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1458 [M+H]+
Trivial name: NodBj-V(Ac C18:1 MeFuc)
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_187036,IEDB_241099,SB_74,SB_85,SB_86

• Article ID: 2668
  Carlson RW, Sanjuan J, Bhat UR, Glushka J, Spaink HP, Wijfjes AHM, Van Brussel AAN, Stokkermans TJW, Peters NK, Stacey G "The structures and biological activities of the lipo-oligosaccharide nodulation signals produced by type I and II strains of Bradyrhizobium japonicum" - Journal of Biological Chemistry 268 (1993) 18372-18381
  

  Bradyrhizobium japonicum produces lipo-oligosaccharide signal molecules that induce deformation of root hairs and meristematic activity on soybeans. B. japonicum USDA135 (a Type I strain) produces modified chitin pentasaccharide molecules with either a terminal N-C16:0- or N-C18:1-glucosamine with and without an O-acetyl group at C-6 and with 2-O-methylfucose linked to C-6 of the reducing N-acetylglucosamine. An additional molecule has N-C16:1-glucosamine and no O-acetyl group. All of these molecules cause root hair deformation on Vicia sativa and Glycine soja. The C18:1-containing molecules were tested and found to induce meristem formation on G. soja. USDA61 (a Type II strain) produces eight additional molecules. Five have a carbamoyl group on the terminal N-acylglucosamine. Six have chitin tetrasaccharide backbones. Three have a terminal N-acyl-N-methylglucosaminosyl residue. In four molecules, the reducing-end N-acetylglucosamine is glycosidically linked to glycerol and has a branching fucosyl, rather than a 2-O-methylfucosyl, residue. One molecule has a terminal N-acylglucosamine that has both acetyl and carbamoyl groups (one each).

  NCBI PubMed ID: 8349712
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, Department of Microbiology and the Center for Legume Research, University of Tennessee, Knoxville, lknnessee 37996, Institute of Molecular Plant Sciences, Leiden University, 2311 VJ Leiden, The Netherlands, Ohio State Biotechnology Center, Ohio State University, Columbus, Ohio 43210
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, TLC, biological assays, composition analysis, NMR-1D
  
   
  
  Bradyrhizobium japonicum USDA61, Bradyrhizobium japonicum USDA135
  CSDB ID 31399 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1473 [M+H]+
Trivial name: NodBj-V(Cb C18:1 NMe MeFuc)
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_241099,SB_74,SB_85,SB_86

• Article ID: 2668
  Carlson RW, Sanjuan J, Bhat UR, Glushka J, Spaink HP, Wijfjes AHM, Van Brussel AAN, Stokkermans TJW, Peters NK, Stacey G "The structures and biological activities of the lipo-oligosaccharide nodulation signals produced by type I and II strains of Bradyrhizobium japonicum" - Journal of Biological Chemistry 268 (1993) 18372-18381
  

  Bradyrhizobium japonicum produces lipo-oligosaccharide signal molecules that induce deformation of root hairs and meristematic activity on soybeans. B. japonicum USDA135 (a Type I strain) produces modified chitin pentasaccharide molecules with either a terminal N-C16:0- or N-C18:1-glucosamine with and without an O-acetyl group at C-6 and with 2-O-methylfucose linked to C-6 of the reducing N-acetylglucosamine. An additional molecule has N-C16:1-glucosamine and no O-acetyl group. All of these molecules cause root hair deformation on Vicia sativa and Glycine soja. The C18:1-containing molecules were tested and found to induce meristem formation on G. soja. USDA61 (a Type II strain) produces eight additional molecules. Five have a carbamoyl group on the terminal N-acylglucosamine. Six have chitin tetrasaccharide backbones. Three have a terminal N-acyl-N-methylglucosaminosyl residue. In four molecules, the reducing-end N-acetylglucosamine is glycosidically linked to glycerol and has a branching fucosyl, rather than a 2-O-methylfucosyl, residue. One molecule has a terminal N-acylglucosamine that has both acetyl and carbamoyl groups (one each).

  NCBI PubMed ID: 8349712
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, Department of Microbiology and the Center for Legume Research, University of Tennessee, Knoxville, lknnessee 37996, Institute of Molecular Plant Sciences, Leiden University, 2311 VJ Leiden, The Netherlands, Ohio State Biotechnology Center, Ohio State University, Columbus, Ohio 43210
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, TLC, biological assays, composition analysis, NMR-1D
  
   
  
  Bradyrhizobium japonicum USDA61
  CSDB ID 136718 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1501 [M+H]+
Trivial name: NodBj-V(Ac Cb C18:1 NMe MeFuc)
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_241099,SB_74,SB_85,SB_86

• Article ID: 2668
  Carlson RW, Sanjuan J, Bhat UR, Glushka J, Spaink HP, Wijfjes AHM, Van Brussel AAN, Stokkermans TJW, Peters NK, Stacey G "The structures and biological activities of the lipo-oligosaccharide nodulation signals produced by type I and II strains of Bradyrhizobium japonicum" - Journal of Biological Chemistry 268 (1993) 18372-18381
  

  Bradyrhizobium japonicum produces lipo-oligosaccharide signal molecules that induce deformation of root hairs and meristematic activity on soybeans. B. japonicum USDA135 (a Type I strain) produces modified chitin pentasaccharide molecules with either a terminal N-C16:0- or N-C18:1-glucosamine with and without an O-acetyl group at C-6 and with 2-O-methylfucose linked to C-6 of the reducing N-acetylglucosamine. An additional molecule has N-C16:1-glucosamine and no O-acetyl group. All of these molecules cause root hair deformation on Vicia sativa and Glycine soja. The C18:1-containing molecules were tested and found to induce meristem formation on G. soja. USDA61 (a Type II strain) produces eight additional molecules. Five have a carbamoyl group on the terminal N-acylglucosamine. Six have chitin tetrasaccharide backbones. Three have a terminal N-acyl-N-methylglucosaminosyl residue. In four molecules, the reducing-end N-acetylglucosamine is glycosidically linked to glycerol and has a branching fucosyl, rather than a 2-O-methylfucosyl, residue. One molecule has a terminal N-acylglucosamine that has both acetyl and carbamoyl groups (one each).

  NCBI PubMed ID: 8349712
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, Department of Microbiology and the Center for Legume Research, University of Tennessee, Knoxville, lknnessee 37996, Institute of Molecular Plant Sciences, Leiden University, 2311 VJ Leiden, The Netherlands, Ohio State Biotechnology Center, Ohio State University, Columbus, Ohio 43210
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, TLC, biological assays, composition analysis, NMR-1D
  
   
  
  Bradyrhizobium japonicum USDA61
  CSDB ID 31400 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1390 [M+H]+
Trivial name: NodBj-V (C16:0 MeFuc)
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141181,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_151531,IEDB_152214,IEDB_153212,IEDB_174333,IEDB_241099,SB_74,SB_85,SB_86

• Article ID: 2668
  Carlson RW, Sanjuan J, Bhat UR, Glushka J, Spaink HP, Wijfjes AHM, Van Brussel AAN, Stokkermans TJW, Peters NK, Stacey G "The structures and biological activities of the lipo-oligosaccharide nodulation signals produced by type I and II strains of Bradyrhizobium japonicum" - Journal of Biological Chemistry 268 (1993) 18372-18381
  

  Bradyrhizobium japonicum produces lipo-oligosaccharide signal molecules that induce deformation of root hairs and meristematic activity on soybeans. B. japonicum USDA135 (a Type I strain) produces modified chitin pentasaccharide molecules with either a terminal N-C16:0- or N-C18:1-glucosamine with and without an O-acetyl group at C-6 and with 2-O-methylfucose linked to C-6 of the reducing N-acetylglucosamine. An additional molecule has N-C16:1-glucosamine and no O-acetyl group. All of these molecules cause root hair deformation on Vicia sativa and Glycine soja. The C18:1-containing molecules were tested and found to induce meristem formation on G. soja. USDA61 (a Type II strain) produces eight additional molecules. Five have a carbamoyl group on the terminal N-acylglucosamine. Six have chitin tetrasaccharide backbones. Three have a terminal N-acyl-N-methylglucosaminosyl residue. In four molecules, the reducing-end N-acetylglucosamine is glycosidically linked to glycerol and has a branching fucosyl, rather than a 2-O-methylfucosyl, residue. One molecule has a terminal N-acylglucosamine that has both acetyl and carbamoyl groups (one each).

  NCBI PubMed ID: 8349712
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens 30602-4712, Department of Microbiology and the Center for Legume Research, University of Tennessee, Knoxville, lknnessee 37996, Institute of Molecular Plant Sciences, Leiden University, 2311 VJ Leiden, The Netherlands, Ohio State Biotechnology Center, Ohio State University, Columbus, Ohio 43210
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, TLC, biological assays, composition analysis, NMR-1D
  
   
  
  Bradyrhizobium japonicum USDA135
  CSDB ID 136719 (all data & tools)