Identification of N epsilon-[(R)-1-carboxyethyl]-L-lysine in, and the complete structure of, the repeating unit of the O-specific polysaccharide of Providencia alcalifaciens O23.
N epsilon-[(R)-1-Carboxyethyl]-L-lysine was released by acid hydrolysis from the O-specific polysaccharide of Providencia alcalifaciens O23 and identified by 1H and 13C NMR spectroscopy, GLC-MS after conversion to a di-N-acetylated dimethyl ester, and by comparison with the authentic sample. Solvolysis of the polysaccharide with anhydrous HF resulted in an amide of D-glucuronic acid with N epsilon-[(R)-1-carboxyethyl]-L-lysine. These and published data allowed the determination of the full structure of the repeating unit of the O-specific polysaccharide.
Kocharova
N A
NA
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
Vinogradov
E V
EV
Borisova
S A
SA
Shashkov
A S
AS
Knirel
Y A
YA
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D008401:Gas Chromatography-Mass Spectrometry; D008239:Lysine / Q000031:analogs & derivatives* / Q000032:analysis; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D019081:O Antigens / Q000737:chemistry* / Q000302:isolation & purification; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D009904:Optical Rotation; D011532:Providencia / Q000737:chemistry*
D019081:O Antigens; D009844:Oligosaccharides; C054688:N(6)-(1-carboxyethyl)lysine; D008239:Lysine