Configuration of the acetal carbon atom of pyruvic acid acetals in some bacterial polysaccharides

The configuration at the acetal carbon atom of pyruvic acid acetals present in some extracellular bacterial polysaccharides has been investigated. Assignment of the absolute configuration was made by comparing signals in the 13C- and 1H-n.m.r. spectra of the polysaccharides with those of model subst...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate research 1980-01, Vol.78 (1), p.127-132
Main Authors: Garegg, Per J., Jansson, Per-Erik, Lindberg, Bengt, Lindh, Frank, Lönngren, Jörgen, Kvarnström, Ingemar, Nimmich, Wolfgang
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The configuration at the acetal carbon atom of pyruvic acid acetals present in some extracellular bacterial polysaccharides has been investigated. Assignment of the absolute configuration was made by comparing signals in the 13C- and 1H-n.m.r. spectra of the polysaccharides with those of model substances. The S-configuration was demonstrated in eight polysaccharides in which pyruvic acid is linked to O-4 and O-6 of D-glucopyranosyl or D-mannopyranosyl residues. The R-configuration was demonstrated in four polysaccharides in which pyruvic acid is linked to O-4 and O-6 of D-galactopyranosyl residues. Consequently, in each of these acetals, which form 1,3-dioxane rings, the methyl group is equatorial and the carboxyl group axial. The S-form was further demonstrated in four polysaccharides in which the pyruvic acid is linked to O-3 and O-4 of D-galactopyranosyl groups.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)83666-6