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Year 2005, Month 5 (Section Full Articles, Page 1276)

Structure of the O-polysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 containing a new higher branched monosaccharide*

S. N. Senchenkova, A. S. Shashkov, Yu. A. Knirel,* M. Ahmed, A. Mavridis, and K. Rudolph

An O-polysaccharide was prepared by mild acid hydrolysis of a lipopolysaccharide of Erwinia carotovora ssp. atroseptica GSPB 9205 and was found to contain a new higher branched monosaccharide, viz., 3,6,8-trideoxy-4-C-(R-1-hydroxyethyl)-D-gulo-octose, which we called erwiniose. The structure of the pentasaccharide repeating unit of the O-polysaccharide was established by monosaccharide analysis, including the determination of absolute configura- tions, methylation analysis, O-deacetylation, Smith degradation, and one- and two-dimen- sional NMR spectroscopy. The configuration of erwiniose was determined based on the cou- pling constants of vicinal protons combined with the nuclear Overhauser effect data and the results of periodate oxidation of the polysaccharide followed by reduction of the resultant 4-keto sugar (the C(1)—C(4)—C(1´)—C(2´) fragment) to give 3,6-dideoxy-D-ribo-hexose (paratose) and oxidation of 3-hydroxybutyraldehyde (the C(5)—C(8) fragment) to give R-3-hydroxybutyric acid.

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