title: Rhizobium fredii synthesizes an array of lipooligosaccharides, including a novel compound with glucose inserted into the backbone of the molecule.
abstract: Flavonoid cues from the plant host cause symbiotic, nitrogen-fixing rhizobia to synthesize lipochitooligosaccharides (LCOs), which act as return signals to initiate the nodulation process. Rhizobium fredii strain USDA257 is known to produce four LCOs, all substituted with vaccenic acid (C18:1). We show here that a mutant strain can replace vaccenic acid with a C16:0 side chain, and that strain USDA191 synthesizes additional LCOs that differ from one another in the length and unsaturation of their fatty acyl substituents. USADA191 and 257DH4 both produce a novel LCO with glucose substituted for N-acetyl-D-glucosamine in the backbone of the molecule.
authors.affiliation: Institut de Pharmacologie et de Biologie Structurale du Centre National de la Recherche Scientifique, Toulouse, France.
authors.forename: M P
authors.initials: MP
authors.lastname: Bec-Ferté
authors.forename: H B
authors.initials: HB
authors.lastname: Krishnan
authors.forename: A
authors.initials: A
authors.lastname: Savagnac
authors.forename: S G
authors.initials: SG
authors.lastname: Pueppke
authors.forename: J C
authors.initials: JC
authors.lastname: Promé
mesh_terms: D000117:Acetylglucosamine / Q000032:analysis / Q000378:metabolism; D000942:Antigens, Bacterial; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002686:Chitin; D002851:Chromatography, High Pressure Liquid; D005419:Flavonoids / Q000378:metabolism; D005947:Glucose / Q000032:analysis / Q000378:metabolism; D008070:Lipopolysaccharides / Q000096:biosynthesis* / Q000737:chemistry; D008961:Models, Structural; D008969:Molecular Sequence Data; D009829:Oleic Acids / Q000378:metabolism; D010944:Plants / Q000382:microbiology; D012231:Rhizobium / Q000378:metabolism*; D018629:Spectrometry, Mass, Secondary Ion; D013559:Symbiosis
chemical_list: D000942:Antigens, Bacterial; D005419:Flavonoids; D008070:Lipopolysaccharides; D009829:Oleic Acids; C023023:lipid-linked oligosaccharides; D002686:Chitin; C050413:11-octadecenoic acid; D005947:Glucose; D000117:Acetylglucosamine