Structures of cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106T

Abstract

Structures of two cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106 were studied. The structure of mannitol teichoic acid described earlier was mainly confirmed. This polymer is 1,6-poly(mannitol phosphate) bearing beta-D-glucopyranosyl residues at the C-2 of mannitol and pyruvic acid residues at the C-4 and C-5. The absolute configurations of D-mannitol and S-pyruvic acid were found. The following distinctions from the earlier described structure were found: unsubstituted 1,6-poly(mannitol phosphate) residues and residues substituted only by beta-D-glucopyranosyl at the C-2 of mannitol but unsubstituted by pyruvic acid are present in the chain. The structure of glycerol teichoic acid present in the cell wall as a minor component (approximately 7%) is also described. This acid is identified as 1,3-poly(glycerol phosphate) substituted at the C-2 of glycerol by 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residues bearing R-pyruvic acid residues at the C-4 and C-6 of galactose. This polymer is for the first time described in the cell wall of Gram-positive bacteria.