Cell wall glycopolymers of Streptomyces albus, Streptomyces albidoflavus and Streptomyces pathocidini

Abstract

The cell wall glycopolymers of three strains of Streptomyces albus and the type strain of Streptomyces pathocidini were investigated. The structures of the glycopolymers were established using a combination of chemical and NMR spectroscopic methods. The cell wall of S. albus subsp. albus VKM Ac-35(T) was found to be comprised of three glycopolymers, viz. unsubstituted 1,5-poly(ribitol phosphate), 1,3-poly(glycerol phosphate) substituted with β-D-glucopyranose, and the major polymer, a 3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (Kdn)-teichulosonic acid: β-D-Glcp-(1 → 8)-α-Kdnp-(2[(→6)-β-D-Glcp-(1 → 8)-α-Kdnp-(2 →] n 6)-β-D-Glcp-(1 → 8)-β-Kdnp-(2-OH, where n ≥ 3. The cell walls of 'S. albus' J1074 and 'S. albus' R1-100 were found to contain three glycopolymers of identical structures, viz. unsubstituted 1,3- and 2,3-poly(glycerol phosphates), and the major polymer, a Kdn-teichulosonic acid with an unusual structure that has not been previously described: β-D-Galp-(1 → 9)-α-Kdnp-(2[(→3)-β-D-Galp-(1 → 9)-α-Kdnp-(2 →] n 3)-β-D-Galp-(1 → 9)-β-Kdnp-(2-OH, where n ~ 7-8. The cell wall of S. pathocidini (formerly S. albus subsp. pathocidicus) VKM Ac-598(T) was found to contain two glycopolymers, viz. 1,3-poly(glycerol phosphate) partially O-glycosylated with 2-acetamido-2-deoxy-α-D-glucopyranose and/or O-acylated with L-lysine, and a poly(diglycosyl 1-phosphate) of hitherto unknown structure: -6)-α-D-Glcp-(1 → 6)-α-D-GlcpNAc-(1-P-.

Exploring the Impact of Ketodeoxynonulosonic Acid in Host-Pathogen Interactions Using Uptake and Surface Display by Nontypeable Haemophilus influenzae

“…While database mining suggests that Kdn is ancestral compared to Neu5Ac (Fig. 1; see also Files S1 and S2 in the supplemental material), current evidence of Kdn in bacteria is in pathogens of plants (which do not contain any Sia) (30)(31)(32).…”

Exploring anomeric glycosylation of phosphoric acid: Optimisation and scope for non-native substrates

“…To the best of our knowledge this is the first report of an O 1 ,O 6 7-membered cyclic phosphate; an O 1 ,O 3 system was previously reported for D-glucose. [31] Scheme 4. a) Possible mechanism for the formation of cyclic phosphate β-13 b) DFT energy minimised 3 CO conformation for β-13.…”

“…Glycosyl 1-phosphates are key intermediates in carbohydrate primary metabolism and are utilised by microorganisms to form polyphosphate architectures that constitute keys parts of their extracellular capsule and cell walls. [1][2][3][4] They serve as precursors to sugar nucleotides, [5][6] the sugar donor components utilised by glycosyltransferases in the assembly of oligosaccharides and glycans and have played a key role in the development of glycosylated natural-product-based therapeutics. [7] Additionally, glycosyl 1-phosphates have been used as substrates for glycoside phosphorylases, a rapidly expanding [8] family of CAZy enzymes for the synthesis of oligosaccharide targets [9] and also play important technological roles in the food and detergent sectors.…”

Elucidation of the genetic mechanisms contributing to moenomycin resistance in actinobacteria

“…Resistance to cell wall-active antibiotics is often modulated by the structure of cell wall polymers other than peptidoglycan, such as teichoic acids. We analyzed the structure of these cell wall polymers in R1-100 and revealed that they are identical to that of J1074 [9], qualitatively and quantitatively.…”