Teichulosonic Acid, an Anionic Polymer of a New Class from the Cell Wall of Actinoplanes utahensis VKM Ac-674^T

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A. S. Shashkov¹, G. M. Streshinskaya^2*, Yu. I. Kozlova², E. M. Tul’skaya², S. N. Senchenkova¹, N. P. Arbatskii¹, O. V. Bueva³, and L. I. Evtushenko³

¹Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russia; fax: (499) 135-5328; E-mail: shash@ioc.ac.ru

²Faculty of Biology, Lomonosov Moscow State University, 119991 Moscow, Russia; fax: (495) 939-4309; E-mail: streshinskaya@mail.ru

³All-Russian Collection of Microorganisms (VKM), 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 December 21, 2011; Revision received January 28, 2012

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The cell wall of Actinoplanes utahensis VKM Ac-674^T contains two anionic polymers: teichoic acid 1,3-poly(glycerol phosphate) that is widespread in cell walls of Gram-positive bacteria; and a unique teichulosonic acid belonging to a new class of bioglycans described only in microorganisms of the Actinomycetales order. The latter polymer contains residues of di-N-acyl derivative of sialic acid-like monosaccharide – 5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-β-L-manno-non-2-ulosonic or pseudaminic acid (Pse) which bears the N-(3,4-dihydroxybutanoyl) group (Dhb) at C7. This polymer has irregular structure and consists of fragments of two types, which differ in substitution of the Dhb residues at O4 either with β-D-glucopyranose or with β-Pse residues. Most of the β-Pse residues (~80%) are glycosylated at position 4 with α-D-galactopyranose residues in both types of fragments. The glucose, galactose, and Dhb residues are partly O-acetylated. The structures of the polymers were established by chemical and NMR spectroscopy methods.

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KEY WORDS: Actinoplanes utahensis, cell wall, anionic polysaccharides, teichoic acids, teichulosonic acids, NMR spectroscopy

DOI: 10.1134/S0006297912050112

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