Structure of an acidic O-specific polysaccharide from marine bacterium Shewanella fidelis KMM 3582T containing Nepsilon-[(S)-1-carboxyethyl]-Nalpha-(D-galacturonoyl)-L-lysine.
The O-specific polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of the marine bacterium Shewanella fidelis type strain KMM 3582T and studied by sugar analysis along with 1H and 13C NMR spectroscopy including one-dimensional NOE in difference mode and two-dimensional experiments. The polysaccharide was found to consist of linear tetrasaccharide repeating units containing Nepsilon-[(S)-1-carboxyethyl]-Nalpha-(D-galacturonoyl)-L-lysine and having the following structure: [See text.] The amide of D-galacturonic acid with Nepsilon-[(S)-1-carboxyethyl]-L-lysine ('alaninolysine', 2S,8S-AlaLys) was found for the first time in nature as a component of the O-specific polysaccharide of Providencia rustigianii O14 (Carbohydr. Res. 2003, 338, 1009-1016).
Kilcoyne
Michelle
M
Department of Chemistry, National University of Ireland, Galway, Ireland.
Perepelov
Andrei
A
Shashkov
Alexander S
AS
Nazarenko
Evgeny L
EL
Ivanova
Elena P
EP
Gorshkova
Natalya M
NM
Gorshkova
Raisa P
RP
Savage
Angela V
AV
D019342:Acetic Acid / Q000737:chemistry; D000107:Acetylation; D000577:Amides / Q000737:chemistry; D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D006031:Glycosylation; D006868:Hydrolysis; D008070:Lipopolysaccharides / Q000737:chemistry / Q000302:isolation & purification; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D019081:O Antigens / Q000737:chemistry* / Q000276:immunology; D011134:Polysaccharides / Q000737:chemistry* / Q000276:immunology; D020592:Shewanella / Q000737:chemistry*
D000577:Amides; D002247:Carbon Isotopes; D008070:Lipopolysaccharides; D019081:O Antigens; D011134:Polysaccharides; D008239:Lysine; D019342:Acetic Acid