Structure of the O-specific polysaccharide of the bacterium Proteus mirabilis O13 containing a novel component: an amide of D-galacturonic acid with N(epsilon)-(1-carboxyethyl)lysine.
An acidic O-specific polysaccharide was obtained by mild degradation of the lipopolysaccharide of the bacterium Proteus mirabilis O13 and found to contain D-galactose, 2-acetamido-2-deoxy-D-glucose, and N(epsilon)-(1-carboxyethyl)-N(alpha)-(D-galacturonoyl)lysine. On the basis of full acid hydrolysis 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 branched trisaccharide repeating unit of the polysaccharide was established [structure: see text]
Shashkov
A S
AS
Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
Toukach
F V
FV
Senchenkova
S N
SN
Ziolkowski
A
A
Paramonov
N A
NA
Kaca
W
W
Knirel YuA
Kochetkov
N K
NK
D000577:Amides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006603:Hexuronic Acids / Q000737:chemistry*; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D011513:Proteus mirabilis / Q000276:immunology*
D000577:Amides; D006603:Hexuronic Acids; D019081:O Antigens; C007819:galacturonic acid; C054688:N(6)-(1-carboxyethyl)lysine; D008239:Lysine