Structures of Cell Wall Teichoic Acids of Brevibacterium iodinum VKM Ac-2106^T

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N. V. Potekhina^1*, L. I. Evtushenko², S. N. Senchenkova³, A. S. Shashkov³, and I. B. Naumova¹

¹Faculty of Biology, Lomonosov Moscow State University, 119992 Moscow, Russia; E-mail: potekchina@hotbox.ru

²Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142292 Pushchino, Moscow Region, Russia; fax: (7-095) 923-3602

³Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 117913 Moscow, Russia; fax: (7-095) 135-5328

^* To whom correspondence should be addressed.

Received November 28, 2003; Revision received March 6, 2004

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Structures of two cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106^T were studied. The structure of mannitol teichoic acid described earlier was mainly confirmed. This polymer is 1,6-poly(mannitol phosphate) bearing beta-D-glucopyranosyl residues at the C-2 of mannitol and pyruvic acid residues at the C-4 and C-5. The absolute configurations of D-mannitol and S-pyruvic acid were found. The following distinctions from the earlier described structure were found: unsubstituted 1,6-poly(mannitol phosphate) residues and residues substituted only by beta-D-glucopyranosyl at the C-2 of mannitol but unsubstituted by pyruvic acid are present in the chain. The structure of glycerol teichoic acid present in the cell wall as a minor component (~7%) is also described. This acid is identified as 1,3-poly(glycerol phosphate) substituted at the C-2 of glycerol by 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residues bearing R-pyruvic acid residues at the C-4 and C-6 of galactose. This polymer is for the first time described in the cell wall of Gram-positive bacteria.

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KEY WORDS: Brevibacterium, teichoic acids, poly(glycerol phosphate), poly(mannitol phosphate), pyruvic acid acetal, NMR spectroscopy

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