2-Acetamido-4-O-[(S)-1-carboxyethyl]-2-deoxy-d-glucose: a new natural isomer of N-acetylmuramic acid from the O-specific polysaccharide of Proteus penneri 35

✍ Scribed by Yuriy A. Knirel; Nikolay A. Paramonov; Eugeny V. Vinogradov; Nikolay K. Kochetkov; Zygmunt Sidorczyk; Krystina Zych

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 190 KB
• Volume: 259
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84208-6

✦ Synopsis

Recently [1,2], 2-acetamido-3-O-[(R)-and (S)-1-carboxyethyll-2-deoxy-o-glucoses (N-acetylmuramic acid and N-acetylisomuramic acid) have been identified as constituents of the O-specific polysaccharides of Yersinia ruckerii II and Proteus penneri 62, respectively. We report now the isolation and identification of 2acetamido-4-O-[(S)-l-carboxyethyl]-2-deoxy-D-glucose from the O-specific polysaccharide of Proteus penneri 35. The polysaccharide was obtained by mild acid degradation (2% CH,COOH, lOO'C> of the lipopolysaccharide isolated from dry bacterial cells by the phenolwater procedure [3]. Its 13C NMR spectrum showed the presence of OAc groups in a nonstoichiometric amount (6, 21.51, which were removed by treatment with aqueous 10% ammonia (60°C). Conventional sugar analysis of the 0-deacetylated polysaccharide revealed rhamnose, glucose, galactose, and 2-amino-Zdeoxyglucose in the ratios N 2 : 1: 1: 1. As judged by the 'H and 13C NMR spectra, the polysaccharide has a hexasaccharide repeating unit (there were signals for six anomeric protons in the region 4.53-5.60 ppm and carbons in the region 99.6-103.6 ppm). It contains two Gdeoxyhexoses [signals for H-6 at 6 1.25 and 1.32 (each 3 H, d, J5,6 6 Hz) and C-6 at 6 18.0 (2 C)], two N-acetylated amino sugars [signals for carbons bearing nitrogen at 6 55.9 and 56.5, and for two NAc groups: 6, 2.02 and 2.06; 6, 23.7 and * Author for correspondence.