Structure of a polysaccharide from the lipopolysaccharide of Vibrio vulnificus CECT4602 containing 2-acetamido-2,3,6-trideoxy-3-[(S)- and (R)-3-hydroxybutanoylamino]-L-mannose.
A polysaccharide was isolated by GPC after mild acid treatment of the lipopolysaccharide of Vibrio vulnificus CECT4602 and found to contain L-Rha, D-GlcpNAc and 2-acetamido-2,3,6-trideoxy-3-(3-hydroxybutanoylamino)-L-mannose (L-RhaNAc3NHb). GLC analysis of the trifluoroacetylated (S)-2-octyl esters derived by full acid hydrolysis of the polysaccharide showed that approximately 80% of the 3-hydroxybutanoic acid has the S configuration and approximately 20% the R configuration. The following structure of the polysaccharide was established by (1)H and (13)C NMR spectroscopies, including 2D ROESY and (1)H/(13)C HMBC experiments: [carbohydrate sequence see in text].
Knirel
Yuriy A
YA
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia. knirel@ioc.a.ru
Senchenkova
Sof'ya N
SN
Shashkov
Alexander S
AS
Esteve
Consuelo
C
Alcaide
Elena
E
Merino
Susana
S
Tomás
Juan M
JM
D002240:Carbohydrate Sequence; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry*; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D041261:Vibrio vulnificus / Q000737:chemistry*
D008070:Lipopolysaccharides; D011135:Polysaccharides, Bacterial; D008358:Mannose