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The relative orientation of the lipid and carbohydrate moieties of lipochitooligosaccharides related to nodulation factors depends on lipid chain saturation.

Authors
  • Groves, Patrick
  • Offermann, Stefanie
  • Rasmussen, Martin Ohsten
  • Canada, F Javier
  • Bono, Jean-Jacques
  • Driguez, Hugues
  • Imberty, Anne
  • Jimenez-Barbero, Jesus
Type
Published Article
Journal
Organic & biomolecular chemistry
Publication Date
Apr 21, 2005
Volume
3
Issue
8
Pages
1381–1386
Identifiers
PMID: 15827632
Source
Medline
License
Unknown

Abstract

Lipochitooligosaccharides (LCOs) signal the symbiosis of rhizobia with legumes and the formation of nitrogen-fixing root nodules. LCOs 1 and 2 share identical tetrasaccharide scaffolds but different lipid moieties (1, LCO-IV(C16:1[9Z], SNa) and , LCO-IV(C16:2[2E,9Z], SNa)). The conformational behaviors of both LCOs were studied by molecular modeling and NMR. Modeling predicts that a small lipid modification would result in a different relative orientation of the lipid and tetrasaccharide moieties. Diffusion ordered spectroscopy reports that both LCOs form small aggregates above 1 mM. Nuclear Overhauser spectroscopy (NOESY) data, collected under monomeric conditions, reveals lipid-carbohydrate contacts only for 1, in agreement with the modeling data. The distinct molecular structures of 1 and 2 have the potential to contribute to their selective binding by legume proteins.

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