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

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A. S. Shashkov¹, E. M. Tul’skaya², L. V. Dorofeeva³, L. I. Evtushenko³, and N. V. Potekhina^2,a*

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

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

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

^* To whom correspondence should be addressed.

Received March 20, 2020; Revised April 3, 2020; Accepted April 3, 2020

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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-2104^T (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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KEY WORDS: Glutamicibacter, cell wall, glycosyl 1-phosphate polymer, Kdn-containing teichulosonic acid

DOI: 10.1134/S0006297920050120

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