New Structures of the O-Specific Polysaccharides of Proteus. 4. Polysaccharides Containing Unusual Acidic N-Acyl Derivatives of 4-Amino-4,6-dideoxy-D-glucose

A. N. Kondakova¹, B. Linder², R. Fudala³, S. N. Senchenkova¹, H. Moll², A. S. Shashkov¹, W. Kaca^3,4, U. Zähringer², and Y. A. Knirel^1*

¹Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia; fax: (7-095) 135-5328; E-mail: knirel@ioc.ac.ru

²Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 10, 23845 Borstel, Germany; fax: (49-4537) 188-632

³Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland; fax: (48-42) 678-4932

⁴Swietokrzyska Academy, 25-406 Kielce, Poland

^* To whom correspondence should be addressed.

Received February 19, 2004; Revision received April 5, 2004

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The structures of the O-polysaccharides of the lipopolysaccharides of Proteus mirabilis O7 and O49 were determined by chemical methods, mass spectrometry, including MS/MS, and NMR spectroscopy, including experiments run in an H₂O/D₂O mixture to reveal correlations for NH protons. The O-polysaccharides were found to contain N-carboxyacetyl (malonyl) and N-(3-carboxypropanoyl) (succinyl) derivatives of 4-amino-4,6-dideoxyglucose (4-amino-4-deoxyquinovose, Qui4N), respectively. The behavior of Qui4N derivatives with the dicarboxylic acids under conditions of acid hydrolysis and methanolysis was studied using GLC-MS.

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KEY WORDS: Proteus mirabilis, 4-amino-4,6-dideoxy-D-glucose, malonic acid, succinic acid, aspartic acid, O-polysaccharide, MS/MS

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