A structural investigation has been carried out on the carbohydrate backbone of Vibrio parahaemolyticus O2 lipopolysaccharides (LPS) isolated by dephosphorylation, O-deacylation and N-deacylation. The carbohydrate backbone is a short-chain saccharide consisting of nine monosaccharide units i.e., 1 mol each of D-galactose (Gal), D-glucose (Glc), D-glucuronic acid (GlcA), L-glycero-D-manno-heptose (L,D-Hep), D- glycero-D-manno-heptose (D,D-Hep), 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo), 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2- ulosonic acid (NonlA), and 2 mol of 2-amino-2-deoxy-D-glucose (D- glucosamine, GlcN). Based on the data obtained by NMR spectroscopy, fast-atom bombardment mass spectrometry (FABMS) and methylation analysis, a structure was elucidated for the carbohydrate backbone of O2 LPS. In the native O2 LPS, the 2-amino-2-deoxy-D-glucitol (GlcN-ol) at the reducing end of the nonasaccharide is present as GlcN. The lipid A backbone is a β-D-GlcN-(1→6)-D-GlcN disaccharide as is the case for many Gram-negative bacterial LPS. The lipid A proximal Kdo is substituted by the distal part of the carbohydrate chain at position-5. In the native O2 LPS, D-galacturonic acid, which is liberated from LPS by mild acid treatment or by dephosphorylation in hydrofluoric acid, is present although its binding position is unknown at present
Lipopolysaccharide, NMR, L-glycero-D-manno-heptose, lipopolysaccharides, LPS, structure, Bacterial, microbiology, structural, methylation analysis, analysis, carbohydrate, chain, 3-deoxy-D-manno-oct-2-ulosonic acid, acid, Kdo, lipid, lipid A, NMR spectroscopy, spectrometry, structural analysis, mass spectrometry, methylation, position, spectroscopy, backbone, fast-atom-bombardment, FABMS, Gram-negative, treatment, Vibrio, Vibrio parahaemolyticus, disaccharide, reducing, reducing end, binding, Japan, monosaccharide, case, native, Glucosamine, D-glucose, dephosphorylation, 2-amino-2-deoxy-D-glucitol, 2-amino-2-deoxy-D-glucose, D-galactose, D-galacturonic acid, D-glucuronic acid, GLC, hydrofluoric acid, O-deacylation, pharmaceutical, saccharide
NCBI PubMed ID: 12706972Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kondo@josai.ac.jp
Institutions: Department of Microbiology School of Pharmaceutical Sciences, Josai University, Sakado, 350-0295, Saitama, Japan
Methods: methylation, FAB-MS, NMR, de-O-acylation, dephosphorylation, de-N-acylation
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