A Teichoic Acid of Nocardioides albus VKM Ac-805^T Cell Walls

A. S. Shashkov¹, E. M. Tul'skaya², L. I. Evtushenko³, and I. B. Naumova^2*

¹Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 117913 Russia; fax: (095) 135-5328

²School of Biology, Lomonosov Moscow State University, Moscow, 119899 Russia; fax: (095) 939-4309; E-mail: naumova@1.micro.bio.msu.ru

³Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, 142292 Russia; fax: (095) 923-3602

^* To whom correspondence should be addressed.

Received March 20, 1999; Revision received May 5, 1999

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A teichoic acid of Nocardioides albus VKM Ac-805^T cell walls, a typical species of the genus Nocardioides, contains a poly(glycosylglycerol phosphate). The repeating unit of the polymer has the structure: [figure]. These units are in phosphodiester linkage at C-3 of glycerol and C-3 of beta-D-galactopyranose. beta-D-Galactopyranosyl residues are substituted at C-4 by beta-D-glucopyranose carrying a 4,6-pyruvate ketal group in S-configuration. The presence of pyruvic acid in the majority of repeating units increases the anionic properties of the polymer in comparison with most other common teichoic acids. This is the first report of the occurrence of a beta-D-galactofuranosyl residue in teichoic acids; it probably acts as a terminator of an extending chain of the polymer. The ratio of beta-D-galactopyranosyl to beta-D-galactofuranosyl units is 7:1. The polymer structure was determined by NMR spectroscopy. This type of teichoic acid structure has not been reported previously.

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KEY WORDS: cell wall, teichoic acid, NMR spectroscopy, Nocardioides, pyruvic acid

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