Teichoic, teichulosonic and teichuronic acids in the cell wall of Brevibacterium aurantiacum VKM Ac-2111(Т).

Two different teichoic acids, along with a teichulosonic and a teichuronic acids, were identified in the cell wall of Brevibacterium aurantiacum VKM Ac-2111(Т). One teichoic acid is 1,3-poly(glycerol phosphate) with 2-acetamido-2-deoxy-α-D-galactopyranose and L-glutamic acid as non-stoichiometric substituents at O-2 of the glycerol residue. The second one is a poly(glycosylglycerol phosphate) with -4)-α-D-Galp-(1 → 2)-sn-Gro-(3-P- and/or -6)-α-D-Galp-(1 → 2)-sn-Gro-(3-P- units in the main chain. The structure of the first has not been reported so far, while the latter one is new for actinobacteria. The teichulosonic acid with α-3-deoxy-β-D-glycero-D-galacto-non-2-ulopyranosonic acid (Kdn) and β-D-glucopyranose residues in the backbone represents a novel polymer: → 8)-α-Kdn-(2 → 6)-β-D-Glcp-(1 →. The teichuronic acid has also hitherto unknown structure: → 3)-β-D-Galf(2OAc)0.3-(1 → 3)-β-D-GlcpА-(1 → and is found in members of the genus Brevibacterium for the first time. The polymer structures were elucidated using 1D- and 2D-NMR spectroscopy: (1)H,(1)H COSY, TOCSY, ROESY, (1)H,(13)C HSQC, HSQC-TOCSY, and (1)H,(13)C and (1)H,(31)P HMBC.