NMR and molecular modeling reveal key structural features of synthetic nodulation factors
| Autor: | Maria Morando, F. Javier Cañada, Jean-Marie Beau, Anne Imberty, Boris Vauzeilles, Alessandra Nurisso, Jesús Jiménez-Barbero, Nathalie Grenouillat |
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| Přispěvatelé: | inconnu, Inconnu, Centre de Recherches sur les Macromolécules Végétales (CERMAV), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF) |
| Rok vydání: | 2011 |
| Předmět: |
Lipopolysaccharides
Models Molecular 0106 biological sciences Magnetic Resonance Spectroscopy Molecular model Stereochemistry Molecular Dynamics Simulation Biology Plant Root Nodulation 01 natural sciences Biochemistry Nod factor 03 medical and health sciences Molecular dynamics chemistry.chemical_compound Carbohydrate Conformation Water environment Phenyl group ComputingMilieux_MISCELLANEOUS 030304 developmental biology chemistry.chemical_classification 0303 health sciences Biological activity Glycosidic bond chemistry Rhizosphere Function (biology) 010606 plant biology & botany |
| Zdroj: | Glycobiology Glycobiology, Oxford University Press (OUP), 2011, pp.824-833 |
| ISSN: | 1460-2423 0959-6658 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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