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Structure of the O-Specific Polysaccharide from Shewanella japonica KMM 3601 Containing 5,7-Diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-talo-non-2-ulosonic Acid

E. L. Nazarenko1, A. V. Perepelov2,3*, L. S. Shevchenko1, E. D. Daeva2, E. P. Ivanova1, A. S. Shashkov2, and G. Widmalm3

1Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, pr. 100 let Vladivostoku 159, 690022 Vladivostok, Russia

2Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russia; E-mail: perepel@ioc.ac.ru

3Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden

* To whom correspondence should be addressed.

Received December 24, 2010; Revision received February 7, 2011
Structure of the O-specific polysaccharide chain of the lipopolysaccharide (LPS) of Shewanella japonica KMM 3601 was elucidated. The initial and O-deacylated LPS as well as a trisaccharide representing the O-deacetylated repeating unit of the O-specific polysaccharide were studied by sugar analysis along with 1H and 13C NMR spectroscopy. The polysaccharide was found to contain a rare higher sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-talo-non-2-ulosonic acid (a derivative of 4-epilegionaminic acid, 4eLeg). The following structure of the trisaccharide repeating unit was established: →4)-α-4eLegp5Ac7Ac-(2→4)-β-D-GlcpA3Ac-(1→3)-β-D-GalpNAc-(1→.
KEY WORDS: Shewanella japonica, O-specific polysaccharide, lipopolysaccharide, marine bacteria, NMR spectroscopy, 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-talo-non-2-ulosonic acid

DOI: 10.1134/S0006297911070091