title: Structure of the O-specific polysaccharide of Hafnia alvei PCM 1222 containing 2-aminoethyl phosphate.
abstract: The O-specific polysaccharide of H. alvei strain PCM 1222 has a branched hexasaccharide repeating unit containing D-galactose, L-rhamnose, D-ribose, D-galacturonic acid, and 2-acetamido-2-deoxy-D-glucose in the ratios 1:2:1:1:1, as well as 2-aminoethyl phosphate (EtNP) and O-acetyl groups in nonstoichiometric amounts. The polysaccharide was modified by carboxyl reduction, O-deacetylation, and dephosphorylation with 48% hydrofluoric acid, the last reaction being accompanied by removal of the lateral residue of beta-galactofuranose. The modified polysaccharides were studied by methylation analysis and 1H and 13C NMR spectroscopy, including 2D correlation spectroscopy (COSY), H-detected 1H,13C and 1H,31P heteronuclear multiple-quantum coherence (HMQC), 1D NOE, 2D rotating-frame NOE spectroscopy (ROESY), and 2D combined total correlation spectroscopy (TOCSY) and ROESY (TORO). The following structure of the O-deacetylated polysaccharide was established: [formula: see text] In different batches of the polysaccharide, the content of EtNP varied from 0.35 to 0.55 and that of the O-acetyl groups from 0.05 to 0.4 per repeating unit. It was tentatively suggested that the O-acetyl group is located at position 4 of a rhamnosyl residue.
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
authors.forename: F V
authors.initials: FV
authors.lastname: Toukach
authors.forename: A S
authors.initials: AS
authors.lastname: Shashkov
authors.forename: E
authors.initials: E
authors.lastname: Katzenellenbogen
authors.forename: N A
authors.initials: NA
authors.lastname: Kocharova
authors.forename: A
authors.initials: A
authors.lastname: Czarny
authors.forename: Y A
authors.initials: YA
authors.lastname: Knirel
authors.forename: E
authors.initials: E
authors.lastname: Romanowska
authors.forename: N K
authors.initials: NK
authors.lastname: Kochetkov
mesh_terms: D000615:Aminoethylphosphonic Acid / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004755:Enterobacteriaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000032:analysis / Q000737:chemistry; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D012091:Repetitive Sequences, Nucleic Acid; D017421:Sequence Analysis
chemical_list: D019081:O Antigens; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial; D000615:Aminoethylphosphonic Acid