Relatedness of the O-polysaccharide structures of Escherichia coli O123 and Salmonella enterica O58, both containing 4,6-dideoxy-4-{ N-[( S)-3-hydroxybutanoyl]- d-alanyl}amino- d-glucose; revision of the E. coli O123 O-polysaccharide structure

Abstract

O-Polysaccharides were isolated by mild acid degradation of the lipopolysaccharides of Escherichia coli O123 and Salmonella enterica O58 and studied by chemical methods and 2D 1H and 13C NMR spectroscopy, including experiments in a H 2O/D 2O mixture, which enabled observation of correlations for nitrogen-linked protons. The following structure of the O-polysaccharide of E. coli O123 was established: [Display omitted] where l-Qui pNAc stands for 2-acetamido-2,6-dideoxy- l-glucose and d-Qui4NAlaHb for 4-{ N-[( S)-3-hydroxybutanoyl]- d-alanyl}amino-4,6-dideoxy- d-glucose. The latter was isolated as an ethylene glycol glycoside by three sequential Smith degradations of the O-deacetylated O-polysaccharide. The structure established in this work is at variance with the E. coli O123-polysaccharide structure reported earlier [Clark, C. G.; Kropinski, A. M.; Parolis, H.; Grant, C. C.; Trout-Yakel, K. M.; Franklin, K.; Ng, L. K.; Paramonov, N. A.; Parolis, L. A.; Rahn, K.; Tabor, H. J. Med. Microbiol. 2009, 58, 884–894]. In accordance with the genetic data, the O-polysaccharide of S. enterica O58 has the same structure, except for it lacks the O-acetylation.