Structure of Hexasaccharide 1-Phosphate Polymer from Arthrobacter uratoxydans VKM Ac-1979^T Cell Wall

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N. V. Potekhina^1*, A. S. Shashkov², S. N. Senchenkova², L. V. Dorofeeva³, and L. I. Evtushenko³

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, 117913 Moscow, Russia; fax: (495) 135-5328

³All-Russian Collection of Microorganisms, Russian Academy of Sciences, 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 April 12, 2012; Revision received June 4, 2012

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A hexasaccharide 1-phosphate polymer of original structure and two teichoic acids (TA) belonging to different structural types were found in Arthrobacter uratoxydans VKM Ac-1979^T cell wall. The poly(hexasaccharide 1-phosphate) combines features of teichuronic acids and glycosyl 1-phosphate polymers, and its structure has never been reported earlier. Its composition includes residues of α- and β-D-glucuronic acid as well as α-D-galacto-, β-D-gluco-, α-D-mannopyranose, and 6-O-acetylated 2-acetamido-2-deoxy-α-D-glucopyranose. The phosphodiester bond in the polymer joins the glycoside hydroxyl of α-D-glucuronic acid and O6 of α-D-galactopyranose. TA 1 is β-D-glucosylated 1,3-poly(glycerol phosphate), and TA 2 is 3,6-linked poly[α-D-glucosyl-(1→2)-glycerol phosphate]. The phosphate-containing polymers were studied by chemical methods and on the basis of one-dimensional ¹H-, ¹³C-, and ³¹P-NMR spectra, homonuclear two-dimensional ¹H/¹H COSY, TOCSY, ROESY, and heteronuclear ¹H/¹³C HSQC, HSQC-TOCSY, HMBC, and ¹H/³¹P HMBC experiments. The set and structure of the polymers revealed as well as the cell wall sugars (galactose, glucose, mannose, glucosamine) and glycerol can be used in microbiological practice for taxonomic purposes.

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KEY WORDS: Arthrobacter uratoxydans, cell wall, cell wall sugars, glycosyl 1-phosphate polymer, teichoic acid, NMR spectroscopy

DOI: 10.1134/S0006297912110089

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