NMR and molecular modeling reveal key structural features of synthetic nodulation factors

Glycobiology. 2011 Jun;21(6):824-33. doi: 10.1093/glycob/cwr014. Epub 2011 Mar 17.

Abstract

Nod factors are lipochitoligosaccharides originally produced by the soil bacteria Rhizobia that are involved in the symbiotic process with leguminous plants. Some synthetic analogs of the Nod factors present a strong biological activity, and the conformational behavior of these molecules is of interest for structure/function studies. Nod factor analogs containing an insertion of a phenyl group in the acyl chain at the oligosaccharidic non-reducing end were previously synthesized (Grenouillat N, Vauzeilles B, Bono J-J, Samain E, Beau J-M. 2004. Simple synthesis of nodulation-factor analogues exhibiting high affinity towards a specific binding protein. Angew Chem Int Ed Engl. 43:4644). Conformational studies of natural compounds and synthetic analogs have been performed combining molecular dynamics simulations in explicit water and NMR. Data revealed that the glycosidic head group can adopt only restricted conformations, whereas chemical modifications of the lipid chains, highly flexible in a water environment, influence the global shape of the molecules. Collected structural data could be used in the future to rationalize and understand their biological activity and affinity toward a putative receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Lipopolysaccharides / chemistry*
  • Lipopolysaccharides / metabolism
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Dynamics Simulation
  • Plant Root Nodulation* / physiology
  • Rhizosphere

Substances

  • Lipopolysaccharides
  • lipid-linked oligosaccharides