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Two Glycosyl 1-Phosphate Polymers and Teichulosonic Acid from Glutamicibacter protophormiae VKM Ac-2104T Cell Wall

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Abstract

Two glycosyl 1-phosphate polymers containing monoglycosyl 1-phosphate, -6)-α-D-Glcp-(1-P., and diglycosyl 1-phosphate, -6)-α-D-GalpNAc-(1→6)-α-D-GlcpNAc-(1-P., in the repeating unit were identified in the cell wall of Glutamicibacter protophormiae VKM Ac-2104T (formerly, Arthrobacter protophormiae). The structures of these polymers were described for the first time in prokaryotes. Teichulosonic acid, the third identified polymer, with 3-deoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid (Kdn) and β-D-glucopyranose residues in the main chain, →6)-β-D-Glcp-(1→8)-α-Kdn-(2→, has been previously detected in a number of actinobacteria. The structures of these glycopolymers were established based on the results of chemical analysis and one-dimensional 1H, 13C, and 31P NMR spectroscopy using two-dimensional homonuclear (1H,1H COZY, TOCSY, ROESY) and heteronuclear (1H,13C HSQC, HSQC-TOCSY, HMBC, and 1H,31P HMBC) techniques.

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Abbreviations

COSY:

correlation spectroscopy

HMBC:

heteronuclear multiple bond correlation

HSQC:

proton-detected heteronuclear single quantum correlation

J :

spin-spin coupling constant

Kdn:

3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid

ROESY:

two-dimensional rotating frame nuclear Overhauser effect spectroscopy

TOCSY:

total correlation spectroscopy

TSP:

3-(trimethylsilyl)-2,2,3,3-tetradeuteropropionic acid sodium salt

VKM:

All-Russian Collection of Microorganisms

δC :

δH, δP, chemical shifts of 13C, 1H, and 31P, respectivel

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Funding

The work is a part of the research program CITIS: AAAA-A16-116021660068-1 of the Lomonosov Moscow State University, Faculty of Biology, Department of Microbiology for 2016-2022.

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Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    A. S. Shashkov

  2. Lomonosov Moscow State University, Faculty of Biology, 119991, Moscow, Russia

    E. M. Tul’skaya, L. I. Evtushenko & N. V. Potekhina

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

    L. V. Dorofeeva

Authors
  1. A. S. Shashkov
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  2. E. M. Tul’skaya
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  3. L. V. Dorofeeva
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  4. L. I. Evtushenko
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  5. N. V. Potekhina
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Correspondence to N. V. Potekhina.

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This article does not contain any studies with human participants or animals performed by any of the authors. The authors declare no conflict of interests.

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Shashkov, A., Tul’skaya, E., Dorofeeva, L. et al. Two Glycosyl 1-Phosphate Polymers and Teichulosonic Acid from Glutamicibacter protophormiae VKM Ac-2104T Cell Wall. Biochemistry Moscow 85, 629–635 (2020). https://doi.org/10.1134/S0006297920050120

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  • DOI: https://doi.org/10.1134/S0006297920050120

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