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

Yuriy A Knirel; Sof'ya N Senchenkova; Alexander S Shashkov; Consuelo Esteve; Elena Alcaide; Susana Merino; Juan M Tomás

doi:10.1016/j.carres.2008.12.012

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

Carbohydr Res. 2009 Mar 10;344(4):479-83. doi: 10.1016/j.carres.2008.12.012. Epub 2008 Dec 25.

Authors

Yuriy A Knirel¹, Sof'ya N Senchenkova, Alexander S Shashkov, Consuelo Esteve, Elena Alcaide, Susana Merino, Juan M Tomás

Affiliation

¹ N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia. knirel@ioc.a.ru

PMID: 19128797
DOI: 10.1016/j.carres.2008.12.012

Abstract

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].

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Sequence
Lipopolysaccharides / chemistry*
Magnetic Resonance Spectroscopy
Mannose / analogs & derivatives*
Mannose / chemistry*
Molecular Sequence Data
Polysaccharides, Bacterial / chemistry*
Vibrio vulnificus / chemistry*

Substances

Lipopolysaccharides
Polysaccharides, Bacterial
Mannose