Structure of the O-specific polysaccharide of Hafnia alvei 1204 containing 3,6-dideoxy-3-formamido-D-glucose.
The O-specific polysaccharide of Hafnia alvei strain 1204 has a hexasaccharide repeating unit containing D-mannose, D-glucuronic acid, 2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, and 3,6-dideoxy-3-formamido-D-glucose (Qui3NFo) in the ratios 2:1:1:1:1 as well as O-acetyl groups. On the basis of methylation analysis of the intact, carboxyl-reduced, and Smith-degraded polysaccharide as well as 1D and 2D NMR spectroscopy, including 1D total correlation spectroscopy, 1D NOE spectroscopy, 2D homonuclear shift-correlated spectroscopy (COSY), and 13C,1H heteronuclear COSY, the following structure of the O-deacetylated polysaccharide was established: -->3)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->3)-beta-D-GlcpN Ac-(1--> -->2)-beta-D-Quip3NFo-(1-->3)-alpha-D-GalpNAc-(1-->4)-alpha-D-G lcpA-(1--> Location of the N-formyl group, occurring as two stereoisomers in the ratio approximately 3:1, was determined by an NOE on H-3 Qui3N arising on pre-irradiation of HCO of the minor (E) isomer. The O-acetyl groups are attached in nonstoichiometric amounts at position 3 of GlcA and position 6 of a mannose residue or GlcNAc.
Katzenellenbogen
E
E
L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw.
Romanowska
E
E
Kocharova
N A
NA
Shashkov
A S
AS
Knirel
Y A
YA
Kochetkov
N K
NK
D000116:Acetylgalactosamine / Q000032:analysis; D000117:Acetylglucosamine / Q000032:analysis; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004755:Enterobacteriaceae / Q000737:chemistry* / Q000276:immunology; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000032:analysis; D005947:Glucose / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000032:analysis; D008745:Methylation; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry* / Q000276:immunology; D010504:Periodic Acid
C097947:3,6-dideoxy-3-formamidoglucose; D019081:O Antigens; D010504:Periodic Acid; C009288:metaperiodate; D005947:Glucose; D000116:Acetylgalactosamine; D005944:Glucosamine; D008358:Mannose; D000117:Acetylglucosamine