Somatic antigens of Pseudomonas aeruginosa

Abstract

Lipopolysaccharides from Pseudomonas aeruginosa 01 (Lhnyi classification), 0 3 (Habs classification), 0 1 3 and 014 (Wokatsch classification), and strain NCTC 8505, which is also related to serogroup 0 3 (Habs), have structurally similar 0-specific polysaccharide chains built up of tetrasaccharide repeating units involving L-rhamnose (Rha), 2-acetamido-2-deoxy-~-glucose (GlcNAc), 2-acetamido-2-deoxy-~-galacturonic acid (GalNAcA), and a di-N-acyl derivative of bacillosamine (BacN): 2,4-diacetamido-2,4,6-trideoxy-~-glucose or 2-acetamido-2,4,6-trideoxy-4-[(S)-3-hydroxybutyramido]-~-glucose. The latter derivative was obtained free by solvolysis with hydrogen fluoride of carboxyl-reduced Habs 0 3 polysaccharide, and was identified by 'H-nuclear magnetic resonance spectroscopy and by mass spectrometry of the corresponding methylated alditol. Habs 03, Lhnyi 01, and Wokatsch 014 polysaccharides contained 0-acetyl groups.Solvolysis with hydrogen fluoride of the native Habs 0 3 polysaccharide resulted in selective cleavage of the glycosidic linkages of 6-deoxy sugars to give the trisaccharide fragment involving all three N-acylated amino sugars. Similar solvolysis of NCTC 8505 polysaccharide afforded a mixture of disaccharide and trisaccharide with N,N'-diacetylbacillosamine at the reducing end. Smith degradation of Habs 0 3 polysaccharide resulted in selective oxidation of rhamnose to give a glycoside of a trisaccharide with glyceraldehyde as the aglycone. Smith degradation of NCTC 8505 polysaccharide was complicated by the formation of the glycoside of a trisaccharide with an aglycone of unknown structure. A trisaccharide with rhamnose at the reducing end was also isolated after Smith degradation of the latter polysaccharide.Analysis of the composition and structure of all oligosaccharides obtained, and detailed examination of the ' jc-nuclear magnetic resonance spectra of these oligosaccharides, and of both intact and modified

Somatic antigens of Pseudomonas aeruginosa. The structure of O-specific polysaccharide chains of the lipopolysaccharides from P. aeruginosa O5 (Lanyi) and immunotype 6 (Fisher)

“…The position of the signals for C-5 and C-7 in the region of 46 -54 ppm showed that these carbons carried nitrogen, and the chemical shifts of the signals for C-3 (34.8 ppm) and C-9 (16.2-16.3 ppm) indicated that these carbons entered the deoxy units. The position of the signals of xylose in the spectra of [1][2][3] were in good agreement with the data for methyl B-D-xylopyranoside [24], and hence this monosaccharide occupied the non-reducing terminus of the oligosaccharides. The use of the 13C nuclear magnetic resonance data for the determination of the mode of glycosidation and substitution by 0-acyl and N-acyl groups in I -3 was described above.…”

“…Investigation of the lipopolysaccharides of an opportunistic bacterial pathogen P. aeruginosa showed many [2, 81, acetamidino [5, 6, 91, (R)- [7] and (S)-3-hydroxybutyryl [3] groups.…”

Structural and Serological Characterisation of the O‐Antigenic Polysaccharide of the Lipopolysaccharide from Acinetobacter Haemolyticus Strain ATCC 17906

“…The situation involving two D (or two L) sugars would result in a large upfield shift of C2 (-1.2) and a minor shift of C4 (-O.l), whereas the opposite situation (i.e. either L-D or D-L substitution) would result in two large negative p-effect shifts, as can be seen for D-QuiNAc4NAc substituted by L-GalNAcA [24]. Thus, as the substituting sugar is a-D-GalNAcA and only C2 possesses a large negative shift, the QuiNAc4NAc residue must also be D configurated.…”

“…By using two-dimensional-NMR spectrometric techniques it was possible to confirm both aminouronic acids as a-GalNAcA (residues A and B, see (6 76.83), with reference to the specific unsubstituted residues [24], were indicative of a repeating unit containing two 4-substituted GalNAcA residues and one 3-substituted QuiNAc4NAc residue. The absolute configuration of the QuiNAc4NAc residue was identified by comparing the "C-NMR p-effects of substitution of this residue [C2 -ve p-effect (-2.41), C4 +ve p-effect (+0.05)] with those for the theoretical residue, a 3-substituted residue possessing the gluco configuration and substituted by a sugar possessing the a-D configuration [25], with respect to unsubstituted QuiNAc4NAc [24]. The situation involving two D (or two L) sugars would result in a large upfield shift of C2 (-1.2) and a minor shift of C4 (-O.l), whereas the opposite situation (i.e.…”

“…CMM 1.55 [29], whereas L-alanine has been found amide-bound to uronic acids in two strains of Proteus [26]. 2,4-Diacetamido-2,4,6-trideoxyglucose is now not that uncommon in LPS as considered in the past [24,29,301. The carbohydrate moiety of Alasan, a bioemulsifier isolated from A. radioresistens KA 53, contains several aminouronic acid residues, of which one is probably amide linked to an L-alanine residue [31].…”