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New structures and composition of cell wall teichoic acids from Nocardiopsis synnemataformans, Nocardiopsis halotolerans, Nocardiopsis composta and Nocardiopsis metallicus: a chemotaxonomic value

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Abstract

The structures of the cell wall teichoic acids (TA) from some species of the genus Nocardiopsis were established by chemical and NMR spectroscopic methods. The cell walls of Nocardiopsis synnemataformans VKM Ac-2518T and Nocardiopsis halotolerans VKM Ac-2519T both contain two TA with unique structures—poly(polyol phosphate-glycosylpolyol phosphate)—belonging to the type IV TA. In both organisms, the minor TA have identical structures: poly(glycerol phosphate-N-acetyl-β-galactosaminylglycerol phosphate) with the phosphodiester bond between C-3 of glycerol and C-4 of the amino sugar. This structure is found for the first time. The major TA of N. halotolerans has a hitherto unknown structure: poly(glycerol phosphate-N-acetyl-β-galactosaminylglycerol phosphate), the N-acetyl-β-galactosamine being acetalated with pyruvic acid at positions 4 and 6. The major TA of N. synnemataformans is a poly(glycerol phosphate-N-acetyl-β-galactosaminylglycerol phosphate) with the phosphodiester bond between C-3 of glycerol and C-3 of the amino sugar. The cell walls of Nocardiopsis composta VKM Ac-2520 and N. composta VKM Ac-2521T contain only one TA, namely 1,3-poly(glycerol phosphate) partially substituted with N-acetyl-α-glucosamine. The cell wall of Nocardiopsis metallicus VKM Ac-2522T contains two TA. The major TA is 1,5-poly(ribitol phosphate), each ribitol unit carrying a pyruvate ketal group at positions 2 and 4. The structure of the minor TA is the same as that of N. composta. The results presented correlate well with the phylogenetic grouping of strains and confirm the species and strain specific features of cell wall TA in members of the genus Nocardiopsis.

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Acknowledgments

This work was supported by Grant 13-04-00447 of the Russian Foundation for Basic Research and the programs of Presidium of Russian Academy of Sciences ‘Molecular and Cell Biology’, the Ministry of Education and Science of the Russian Federation (contract no. 16.518.11.7035).

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Authors and Affiliations

  1. School of Biology, MV Lomonosov Moscow State University, Leninskie gory 1 stroenie 12, Moscow, 119991, Russian Federation

    Elena M. Tul’skaya, Galina M. Streshinskaya & Natalia V. Potekhina

  2. ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, Russian Federation

    Alexander S. Shashkov

  3. All-Russian Collection of Microorganisms (VKM), GK Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, 142290, Russian Federation

    Ludmila I. Evtushenko

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  1. Elena M. Tul’skaya
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  2. Alexander S. Shashkov
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  4. Natalia V. Potekhina
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  5. Ludmila I. Evtushenko
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Correspondence to Elena M. Tul’skaya.

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Tul’skaya, E.M., Shashkov, A.S., Streshinskaya, G.M. et al. New structures and composition of cell wall teichoic acids from Nocardiopsis synnemataformans, Nocardiopsis halotolerans, Nocardiopsis composta and Nocardiopsis metallicus: a chemotaxonomic value. Antonie van Leeuwenhoek 106, 1105–1117 (2014). https://doi.org/10.1007/s10482-014-0280-7

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