Disaccharide 1-Phosphate Polymers of Some Representatives of the Bacillus subtilis Group

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N. V. Potekhina^1*, A. S. Shashkov², G. M. Streshinskaya¹, E. M. Tul’skaya¹, S. N. Senchenkova², E. B. Kudryashova³, and A. S. Dmitrenok²

¹Biological Faculty, Lomonosov Moscow State University, 119991 Moscow, Russia; fax: (495) 939-4309; E-mail: potekhina56@mail.ru

²Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russia; fax: (499) 135-5328

³All-Russian Collection of Microorganisms, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, pr. Nauki 5, 142290 Pushchino, Moscow Region, Russia; fax: (495) 956-3370

^* To whom correspondence should be addressed.

Received March 20, 2013; Revision received May 15, 2013

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Disaccharide 1-phosphate polymers as well as teichoic acids of various structures have been found in the cell walls of the representatives of the Bacillus subtilis group, namely Bacillus subtilis subsp. spizizenii VKM B-720 and VKM B-916, B. subtilis VKM B-517, and Bacillus vallismortis VKM B-2653^T. Disaccharide 1-phosphate polymers are composed of repeating units of the following structure: -P-4)-β-D-GlcpNAc-(1→6)-α-D-Galp-(1-, the N-acetylglucosamine residues are partially acetylated at positions O3 and O6 (VKM B-720 and VKM B-916); -P-4)-β-D-Glcp-(1→6)-α-D-GlcpNAc-(1-, the glucopyranose residues are partially acetylated at positions O2 or O3 (VKM B-517); -P-6)-α-D-GlcpNH₃⁺/α-D-GlcpNAc-(1→2)-α-D-Glcp-(1-, the N-acetylglucosamine residues are partially deacetylated (VKM B-2653^T). The structures of the two last disaccharide 1-phosphate polymers have not been reported so far for Gram-positive bacteria. The teichoic acids in the studied strains are O-D-alanyl-1,5-poly(ribitol phosphates) substituted with β-D-glucopyranose (VKM B-517, VKM B-720, VKM B-916) or 2-acetamido-2-deoxy-β-D-glucopyranose (VKM B-2653^T). The structures of the phosphate-containing polymers have been studied by chemical methods and by NMR spectroscopy.

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KEY WORDS: glycosyl 1-phosphate polymers, teichoic acids, Bacillus subtilis, Bacillus subtilis subsp. spizizenii, Bacillus vallismortis, NMR spectroscopy

DOI: 10.1134/S000629791310009X

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