Structure of the O-specific polysaccharide of the bacterium Providencia alcalifaciens O23 containing a novel component: an amide of D-glucuronic acid with N(epsilon)-(1-carboxyethyl)lysine.
An acidic O-specific polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of the bacterium Providencia alcalifaciens O23 and found to contain D-glucose, D-galactose, 2-acetamido-2-deoxy-D-galactose, and N epsilon-(1-carboxyethyl)-N alpha-(D-glucuronoyl)lysine. On the basis of full and partial acid hydrolyses, selective solvolysis with anhydrous hydrogen fluoride, and 1H- and 13C-NMR spectroscopy, including two-dimensional correlation spectroscopy (COSY), H-detected heteronuclear 1H, 13C multi-quantum coherence (HMQC), and rotating-frame nuclear Overhauser effect spectroscopy (ROESY), the following structure of the liner tetrasaccharide repeating unit of the polysaccharide was established [structure: see text]
Kocharova
N A
NA
Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
Shcherbakova
O V
OV
Shashkov
A S
AS
Knirel YuA
Kochetkov
N K
NK
Kholodkova
E V
EV
Stanislavsky
E S
ES
D000577:Amides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005965:Glucuronates / Q000737:chemistry*; D020723:Glucuronic Acid; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D011532:Providencia / Q000276:immunology*
D000577:Amides; D005965:Glucuronates; D019081:O Antigens; C054688:N(6)-(1-carboxyethyl)lysine; D020723:Glucuronic Acid; D008239:Lysine