Structural studies of the O-antigenic polysaccharide of the lipopolysaccharide from Acinetobacter (DNA group 11) strain 94 containing 3-amino-3,6-dideoxy-D-galactose substituted by the previously unknown amide-linked L-2-acetoxypropionic acid or L-2-hydroxypropionic acid.
A polysaccharide containing D-Gal, D-GalNAc, 3-(L-2-acetoxypropionamido)-3,6-dideoxy-D-galactose (approximately 80%) and 3-(L-2-hydroxypropionamido)-3,6-dideoxy-D-galactose (approximately 20%) was isolated by mild acid hydrolysis, followed by gel-permeation chromatography, from the phenol-soluble lipopolysaccharide (phenol/water extracted) derived from Acinetobacter strain 94. The polysaccharide, characterised by means of monosaccharide analyses, partial acid hydrolysis, and NMR studies, consisted of a branched tetrasaccharide repeating unit, as depicted below, in which Fucp3Nacyl represents 3-(L-2-hydroxypropionamido)-3,6-dideoxy-D-galactose, in which approximately 80% of the acyl residues are O-acetylated. These Fucp3N derivatives and an O-acetylated acyl group are therefore constituents of bacterial LPS, but to our knowledge are not present in any other natural carbohydrates. [sturcture: see text]
Haseley
S R
SR
Division of Medical and Biochemical Microbiology, Research Centre Borstel, Centre for Medicine and Biosciences, Germany.
Holst
O
O
Brade
H
H
D000150:Acinetobacter / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D000606:Amino Sugars / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007773:Lactates / Q000737:chemistry*; D019344:Lactic Acid / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*
C108162:3-amino-3,6-dideoxygalactose; D000577:Amides; D000606:Amino Sugars; D007773:Lactates; D019081:O Antigens; D019344:Lactic Acid; C006359:alpha-acetolactate