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

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-2518(T) and Nocardiopsis halotolerans VKM Ac-2519(T) 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-ß-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-ß-galactosaminylglycerol phosphate), the N-acetyl-ß-galactosamine being acetalated with pyruvic acid at positions 4 and 6. The major TA of N. synnemataformans is a poly(glycerol phosphate-N-acetyl-ß-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-2521(T) 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-2522(T) 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.

A novel teichuronic acid, the major polymer from the cell wall of Actinoplanes lobatus VKM Ac-676(T.).

The cell wall of Actinoplanes lobatus VKM Ac-676(T) (family Micromonosporaceae; order Actinomycetales; class Actinobacteria) contains two anionic glycopolymers. The major one is a teichuronic acid with a linear structure of the chain and heterogeneous repeating units, consisting of glucopyranose residues and statistically alternating residues of diaminouronic acids having the d-manno,l-gulo and d-gluco configurations in a ratio of 6:3:1, respectively. The teichuronic acid of this structure has not hitherto been found in Gram-positive bacteria. The minor glycopolymer is a teichoic acid of poly(glycosylpolyol phosphate) nature with the repeating unit -6)-[α-d-Manp(1→4)]-ß-d-Galp-(1→2)-snGro-(3-P-. The structures of the glycopolymers were established by chemical methods and NMR spectroscopy.

Novel teichulosonic acid from cell wall of Streptomyces coelicolor M145.

The cell wall of Streptomyces coelicolor M145, a prototrophic plasmidless (SCP1(-) SCP2(-)) variant of strain S. coelicolor A3(2) contains the main glycopolymer represented by Kdn-containing teichulosonic acid with unusual structure which has not been described so far: [structure: see text]. The minor polymer was found to be a poly(diglycosyl 1-phosphate) with the following repeating unit: -6)-α-Galp-(1→6)-α-GlcpNAc-(1-P-. The structures of both glycopolymers were established by using a combination of chemical and NMR spectroscopic methods.

New cell wall glycopolymers of the representatives of the genus Kribbella.

Each of the cell walls of four representatives of the genus Kribbella (order Actinomycetales; suborder Propionibacterineae; family Nocardioidaceae) contains a neutral polysaccharide and an acidic polysaccharide with unusual structures. Common to all four strains studied is a mannan with the following repeating unit: [structure: see text]. In the cell wall of the strain VKM Ac-2541, a teichulosonic acid was identified with a monosaccharide component that has not hitherto been found in Gram-positive bacteria, viz., pseudaminic acid, and an unusual linkage type in the polymeric chain, [structure: see text] where R=capital EN, Cyrillic (45%), alpha-D-Galp3OMe (37%) or alpha-D-Galp2,3OMe (18%). The anionic cell wall components of three other strains are represented by teichuronic acids with a rare constituent, viz., a diaminosugar, 2,3-diacetamido-2,3-dideoxyglucopyranose. The structures of their repeating units differ in the nature of the acidic components: -->4)-beta-D-Manp2,3NAcA-(1-->6)-alpha-D-Glcp2,3NAc-(1--> (VKM capital A, Cyrillicsmall es, Cyrillic-2538 and VKM capital A, Cyrillicsmall es, Cyrillic-2540) and -->4)-beta-D-ManpNAcA-(1-->6)-alpha-D-Glcp2,3NAc-(1--> (VKM capital A, Cyrillicsmall es, Cyrillic-2539). The structures of all the glycopolymers were established by chemical and NMR spectroscopic methods; they are identified in Gram-positive bacteria for the first time.

A novel teichoic acid from the cell wall of Streptomyces sp. VKM Ac-2275.

The cell wall of a pathogenic strain Streptomyces sp. VKM Ac-2275 isolated from potato tubers infected by scab contains a teichoic acid related to poly(glycosylpolyol phosphate) with a repeating unit established by chemical and NMR spectroscopic methods. About 60% of l-rhamnose residues bear an O-acetyl group at O-2 and 20% of the internal glucose residues contain an additional phosphate at C-4. The polymer is built of 5-6 units. This structure is found in bacteria for the first time. The strain is phylogenetically closest to the scab-causing species Streptomyces scabiei and Streptomyces europaeiscabiei, but differs from both these species in morphological and physiological characters and does not produce thaxtomin A, the main phytotoxin produced by S. scabiei.

Cell wall teichoic acids of streptomycetes of the phenetic cluster 'Streptomyces fulvissimus'.

Structures of the anionic polymers of streptomycetes Streptomyces fulvissimus VKM Ac-994(T), Streptomyces longispororuber VKM Ac-1735(T), Streptomyces aureoveticillatus VKM Ac-48(T) and Streptomyces spectabilis INA 00606 belonging to the phenetic cluster 'S. fulvissimus' were investigated by chemical and NMR spectroscopic methods. A teichoic acid from the cell wall of S. spectabilis INA 00606 was studied in more detail, and this was shown to represent 1,3-poly(glycerol phosphate) substituted with glucosamine (alpha-D-GlcNAc) and L-glutamic acid (non-stoichiometric substitution). For the first time, glutamic acid is identified as an acyl substituent in teichoic acids of streptomycetes. The polymer chain is built of the following fragments: Cell walls of other streptomycetes of the phenocluster under study contain 1,3-poly(glycerol phosphates) with glucosamine as a glycosyl substituent at O-2 of the glycerol phosphate units and L-glutamic acid and lysine as O-2 acyl substituents. Not all amino sugar residues in the polymers of these strains are N-acetylated, and the content of the glucosamine and lysine residues in the polymers of different strains is not the same. Despite certain quantitative differences in the structures of the polymers, one may consider streptomycetes of the phenocluster 'S. fulvissimus' as closely related microorganisms, the details of the structures serving as additional criteria for the determination of the species status of a strain under study.

A new neutral polymer from the cell wall of actinomycete Kineosporia aurantiaca VKM Ac-702T.

The major cell wall polymer of Kineosporia aurantiaca VKM Ac-702T a representative of the suborder Frankineae, is a galactomannan with a repeating unit of the following structure: -->3)-beta-D-Galp-(1-->6)-beta-D-Manp-(1-->4)-beta-D-Manp-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Manp-(1-->4)-beta-D-Manp-(1--> that has not been reported so far. This was established using chemical degradation methods and NMR spectroscopy. The polysaccharide identified in the present study provides the second example of neutral galactomannans in actinomycete cell walls. The cell wall of K. aurantiaca VKM Ac-702T also contains a minor teichoic acid, viz., 1,3-poly(glycerol phosphate) partially substituted with alpha-glucosamine residues, only part of which are N-acetylated.

Cell wall anionic polymers of Streptomyces sp. MB-8, the causative agent of potato scab.

The cell wall of Streptomyces sp. MB-8 contains a major teichoic acid, viz., 1,3-poly(glycerol phosphate) substituted with N-acetyl-alpha-D-glucosamine (the degree of substitution is 60%), a minor teichoic acid, viz., non-substituted poly(glycerol phosphate), and a family of Kdn (3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid)-containing oligomers of the following general structure: [carbohydrate structure: see text]. The composition of the oligomers was established using MALDI-TOF mass spectroscopy. The present study provides the second example of the identification of Kdn as a component of cell wall polymers of streptomycetes, which are the causative agents of potato scab.

Novel cell-wall teichoic acid from Nocardiopsis albus subsp. albus as a species-specific marker.

Cell walls of the three Nocardiopsis albus subsp. albus strains, DSM 43377T, 43378 and 43120 contain structurally identical teichoic acids. The cell wall of each strain has three distinct types of teichoic acids: (1) unsubstituted 3,5-poly(ribitol phosphate), (2) 1,3-poly(glycerol phosphate) partially substituted at C-2 with α-N-acetylglucosamine residues, and (3) 1,5-poly(ribitol phosphate) with each ribitol unit carrying a 2,4-pyruvate ketal group. Types 1 and 3 are reported in prokaryotes for the first time. The structure of the teichoic acids was elucidated by chemical analysis and NMR-spectroscopic methods. Structural identity of the teichoic acids from the three strains belonging to the same species may demonstrate the species-specificity of these polymers.