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

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E. L. Nazarenko¹, A. V. Perepelov^2,3*, 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

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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→.

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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

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