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Z Sidorczyk

Publications and source records attributed to Z Sidorczyk.

At least 19 recordsLinked to original sources

New structures of the O-specific polysaccharides of Proteus. 3. Polysaccharides containing non-carbohydrate organic acids.

Four new Proteus O-specific polysaccharides were isolated by mild acid degradation from the lipopolysaccharides of P. penneri 28 (1), P. vulgaris O44 (2), P. mirabilis G1 (O3) (3), and P. myxofaciens (4), and their structures were elucidated using NMR spectroscopy and chemical methods. They were found to contain non-carbohydrate organic acids, including ether-linked lactic acid and amide-linked amino acids, and the following structures of the repeating units were established: [Figure: see text], where (S)-Lac and (R)-aLys stand for (S)-1-carboxyethyl (residue of lactic acid) and N(epsilon)-[(R)-1-carboxyethyl]-L-lysine ("alaninolysine"), respectively. The data obtained in this work and earlier serve as the chemical basis for classification of the bacteria Proteus.

Amino Acids↗

New structures of the O-specific polysaccharides of Proteus. 2. Polysaccharides containing O-acetyl groups.

Structures of five new O-specific polysaccharides of Proteus bacteria were established. Four of them, Proteus penneri 4 (O72), Proteus vulgaris 63/57 (O37), Proteus mirabilis TG 277 (O69), and Proteus penneri 20 (O17), contain O-acetyl groups in non-stoichiometric quantities, and the polysaccharide of P. penneri 1 is structurally related to that of P. penneri 4. The structures were elucidated using NMR spectroscopy, including one-dimensional 1H- and 13C-NMR spectroscopy, two-dimensional 1H,1H correlation (COSY, TOCSY), H-detected 1H,13C heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY or ROESY), along with chemical methods. The structural data obtained are useful as the chemical basis for the creation of the classification scheme for Proteus strains.

Carbohydrate Conformation↗

New structures of the O-specific polysaccharides of bacteria of the genus Proteus. 1. Phosphate-containing polysaccharides.

The O-specific polysaccharide chains (O-antigens) of the lipopolysaccharides of five Proteus strains, P. vulgaris O17, P. mirabilis O16 and O33, and P. penneri 31and 103, were found to contain phosphate groups that link the non sugar components, e.g., ethanolamine and ribitol. The polysaccharides of P. mirabilis O16 and P. penneri 103 include ribitol phosphate in the main chain and thus resemble ribitol teichoic acids of Gram-positive bacteria. The structures of the polysaccharides were elucidated using NMR spectroscopy, including two-dimensional 1H,1H correlation spectroscopy (COSY and TOCSY), nuclear Overhauser effect spectroscopy (NOESY or ROESY), and H-detected 1H,13C and 1H,31P heteronuclear multiple-quantum coherence spectroscopy (HMQC), along with chemical methods. The structures determined are unique among the bacterial polysaccharides and, together with the data obtained earlier, represent the chemical basic for classification of Proteus strains. Based on structural similarities of the O-specific polysaccharides and serological relationships between the O-antigens, we propose to extend Proteus serogroups O17 and O19 by including P. penneri strains 16 and 31,respectively.

Carbohydrate Conformation↗

Structure of the O-specific polysaccharide of Proteus mirabilis O16 containing ethanolamine phosphate and ribitol phosphate.

The O-specific polysaccharide of Proteus mirabilis O16 was studied by 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, H-detected 1H,13C HMQC, HMQC-TOCSY, and 1H,31P HMQC experiments, along with chemical methods. The polysaccharide was found to be a ribitol teichoic acid-like polymer having the following structure [structure: see text].

Carbohydrate Conformation↗

The structure of the carbohydrate backbone of the core-lipid A region of the lipopolysaccharide from Proteus penneri strain 40: new Proteus strains containing open-chain acetal-linked N-acetylgalactosamine in the core part of the LPS.

Analysis of the core part of the LPS from several strains of Proteus revealed that P. penneri strains 2, 11, 19, 107, and P. vulgaris serotypes 04 and 08 have the same structure with a new type of linkage between monosaccharidesan open-chain acetal--that was previously determined for P. vulgaris OX2 and P. penneri 17. The LPS from P. penneri strain 40 contains the same structure substituted with one additional monosaccharide: [molecular structure: see text] where (1S)-GalaNAc1 is a residue of N-acetyl-D-galactosamine in the open-chain form. It is connected as a cyclic acetal to positions 4 and 6 of the galactosamine residue having a free amino group. All other sugars are in the pyranose form.

Acetals↗

Structure of the O-specific polysaccharide of Proteus mirabilis D52 and typing of this strain to Proteus serogroup O33.

The acidic O-specific polysaccharide chain (O-antigen) of the lipopolysaccharide (LPS) of Proteus mirabilis strain D52 was studied using chemical analyses along with 1H-NMR and 13C-NMR spectroscopy, including 2D COSY, TOCSY, ROESY, H-detected 1H,13C and 1H,31P HMQC experiments. The polysaccharide was found to contain D-ribitol 5-phosphate (D-Rib-ol-5-P) and ethanolamine phosphate (Etn-P) and has the following structure: D-Rib-ol-5-P (3) approximately 75% EtnP(6)-->2)-beta-D-Galp-(1-->3)-alpha-D-GlcpNAc-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-GlcpNAc-(1-->). This structure is identical with that of the O-polysaccharide of P. mirabilis O33 strain 59/57, and, hence, P. mirabilis D52 belongs to the same Proteus serogroup O33. Serological studies with O-antiserum against P. mirabilis D52 confirmed this but showed that the LPS species of P. mirabilis 59/57 and D52 are not identical, having different epitopes in the core region. A serological cross-reactivity of P. mirabilis D52 O-antiserum was observed with LPS of two other Proteus strains, P. mirabilis O16 and P. penneri 103, which have structurally different O-polysaccharides. The role of charged groups, Rib-ol-5-P and Etn-P in the immunospecificity is discussed.

Animals↗

The structure of the core part of Proteus penneri strain 16 lipopolysaccharide.

The structure of the carbohydrate backbone of the lipid A-core region of the lipopolysaccharide (LPS) from Proteus penneri strain 16 was determined using NMR and chemical analysis of the core oligosaccharide, obtained by mild acid hydrolysis of the LPS, and of the products of alkaline deacylation of the LPS: formula [see text]. Incomplete substitution is indicated by bold italics. All sugars are in the pyranose form, alpha-Hep is the residue of L-glycero-alpha-D-manno-Hep, alpha-DD-Hep is the residue of D-glycero-alpha-D-manno-Hep, Bu is the (R)-3-hydroxybutyryl residue.

Carbohydrate Conformation↗

Structure of a 2-aminoethyl phosphate-containing O-specific polysaccharide of Proteus penneri 63 from a new serogroup O68.

Lipopolysaccharide of Proteus penneri strain 63 was degraded by mild acid to give a high molecular mass O-specific polysaccharide that was isolated by gel-permeation chromatography. Sugar and methylation analyses and NMR spectroscopic studies, including two-dimensional 1H, 1H COSY, TOCSY rotating-frame NOE spectroscopy, H-detected 1H,13C and 1H,31P heteronuclear multiple-quantum coherence (HMQC), and 1H, 13C HMQC-TOCSY experiments, demonstrated the following structure of the polysaccharide: where FucNAc is 2-acetamido-2,6-dideoxygalactose and PEtn is 2-aminoethyl phosphate. The polysaccharide studied shares some structural features, such as the presence of D-GlcNAc6PEtn and an alpha-L-FucNAc-(1-->3)-D-GlcNAc disaccharide, with other Proteus O-specific polysaccharides. A marked cross-reactivity of P. penneri 63 O-antiserum with P. vulgaris O12 was observed and substantiated by a structural similarity of the O-specific polysaccharides of the two strains. In spite of this, the polysaccharide of P. penneri 63 has the unique structure among Proteus O-antigens, and therefore a new, separate serogroup, O68, is proposed for this strain.

Carbohydrate Conformation↗

Structure of the O-specific polysaccharide of Proteus penneri 71 and classification of cross-reactive P. penneri strains to a new proposed serogroup O64.

A neutral O-specific polysaccharide (O-antigen) was isolated from the lipopolysaccharide (LPS) of the bacterium Proteus penneri 71. On the basis of sugar analysis and 1H- and 13C-NMR spectroscopic studies, including two-dimensional COSY, 13C,1H heteronuclear COSY and ROESY, the following structure of the trisaccharide repeating unit of the polysaccharide was established: -->3)-beta-D-GlcpNAc-(1-->4)-beta-D-GlcpNAc-(1-->3)-alpha-D-Galp-(1-- > The polysaccharide has the same carbohydrate backbone as the O-specific polysaccharide of P. penneri 19 and both are similar to that of P. penneri 62 studied by us previously. A cross-reactivity of anti-P. penneri 71, 19 and 62 O-antisera with 11 P. penneri strains was revealed and substantiated at the level of the O-antigen structures. These strains could be divided into three subgroups within a new proposed Proteus O64 serogroup containing P. penneri strains only.

Animals↗

Structure of a 2-aminoethyl phosphate-containing O-specific polysaccharide of Proteus penneri 8 from a new serogroup O67.

An acidic O-specific polysaccharide was obtained by mild acid degradation of the Proteus penneri 8 lipopolysaccharide and found to contain D-glucose, D-galacturonic acid, 2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, 2-acetamido-2,6-dideoxy-L-galactose (L-FucNAc) and 2-aminoethyl phosphate (PEtn) in the ratios 2 : 1 : 1 : 1 : 1 : 1. 1H and 13C NMR spectroscopy was applied to the intact and dephosphorylated polysaccharides, and the following structure of the hexasaccharide repeating unit was established: The O-specific polysaccharide has a unique structure, and, accordingly, we propose for P. penneri 8 a new Proteus O67 serogroup, in which this strain is at present the single representative. The nature of epitopes on LPS of P. penneri 34, P. mirabilis O16, P. mirabilis O23 and P. vulgaris O22, which cross-react with O-antiserum against P. penneri 8, is discussed.

Animals↗

Structure of the O-specific polysaccharide of a serologically separate strain Proteus penneri 2 from a new proposed serogroup O66.

O-specific polysaccharide chain of Proteus penneri strain 2 lipopolysaccharide was studied by full and partial acid hydrolysis, Smith degradation, methylation analysis, and NMR spectroscopy, including two-dimensional rotating-frame NOE spectroscopy (ROESY) and 1H,13C heteronuclear multiple-quantum coherence (HMQC) experiments. Together with D-glucose and 2-acetamido-2-deoxy-D-glucose, the polysaccharide was found to contain two rarely occurring sugars, 6-deoxy-L-talose (L-6dTal) and 2,3-diacetamido-2,3,6-trideoxy-L-mannose (L-RhaNAc3NAc), and the following structure of a non-stoichiometrically O-acetylated tetrasaccharide repeating unit was established: [equation: see text] The O-specific polysaccharide studied has a unique composition and structure and, accordingly, P. penneri 2 is serologically separate among Proteus strains. Therefore, we propose for P. penneri 2 a new Proteus O-serogroup O66 where this strain is at present the single representative.

Carbohydrate Conformation↗

Structure and cross-reactivity of the O-specific polysaccharide of Proteus penneri strain 26, another neutral Proteus O-antigen containing 2-acetamido-2,6-dideoxy-L-glucose (N-acetyl-L-quinovosamine).

A neutral O-specific polysaccharide obtained from the lipopolysaccharide of Proteus penneri strain 26 was studied using sugar analysis and 1H and 13C NMR spectroscopy, including two-dimensional NMR techniques. The following structure of the trisaccharide repeating unit was established: -->6)-alpha-D-GlcpNAc-(1-->3)-alpha-L-QuipNAc-(1-->3)-alpha-D-Glcp NAc-(1--> where L-QuiNAc is 2-acetamido-2,6-dideoxy-L-glucose (N-acetyl-L-quinovosamine). Cross-reactivity of the Proteus penneri 26 anti-O serum with other strains of P. penneri isolated in Poland and USA and one strain of P. vulgaris is discussed.

Acetylglucosamine↗

Structure of the O-specific polysaccharide of a serologically separate Proteus penneri strain 22.

The O-specific polysaccharide chain (O-antigen) of Proteus penneri strain 22 lipopolysaccharide was studied using chemical methods, including partial acid hydrolysis and Smith degradation, as well as one- and two-dimensional 1H and 13C NMR spectroscopy. The following structure of the pentasaccharide repeating unit was established: [sequence: see text] The O-specific polysaccharide contains a GalNAc residue in the furanose form which has not been hitherto found in bacterial polysaccharides. The O-antigen studied is serologically and structurally unique among Proteus strains and, therefore, a new Proteus serogroup O63 is proposed for P. penneri strain 22.

Carbohydrate Conformation↗

Structure of a new neutral O-specific polysaccharide of Proteus penneri 34.

The O-specific polysaccharide of Proteus penneri strain 34 was studied using 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, and H-detected 1H, 13C HMQC experiments. The following structure was established, which is unique among the known structures of Proteus O-antigens:-->4)-beta-D-Glcp-(1-->3)-beta-D-GalpNAc-(1-->4)-beta- D-GalpNAc-(1-->4)-beta-D-Galp-(1-->. Accordingly, no cross-reaction was observed between P. penneri 34 O-antiserum and O-antigens of other Proteus strains. Therefore, the strain studied should belong to a new Proteus serogroup O65.

Animals↗

Structure of the O-specific polysaccharide of Proteus penneri strain 41 from a new proposed serogroup O62.

O-specific polysaccharide of Proteus penneri strain 41 was studied using 1H- and 13C-NMR spectroscopy, including two-dimensional COSY, heteronuclear 13C,1H-correlation (HETCOR) and one-dimensional NOE spectroscopy, and the following structure of a non-stoichiometrically O-acetylated hexasaccharide repeating unit was established:[structure: see text] where RGlcNAc is 2-acetamido-4-O-[(S)-1-carboxyethyl]-2-deoxyglucose. Cross-reactivity of anti-P. penneri 41 O-serum with other P. penneri strains is discussed, and a new, separate O62 serogroup is proposed which is the next Proteus O-serogroup containing P. penneri strains only.

Animals↗

Structure of the O-specific polysaccharide of Proteus penneri strain 25 containing N-(L-alanyl) and multiple O-acetyl groups in a tetrasaccharide repeating unit.

Based on sugar and methylation analyses, O-deacetylation, Smith degradation, and 1H and 13C NMR spectroscopy, including 2D COSY, 1H-detected 1H, 13C heteronuclear single-quantum coherence (HSQC), and 1H-detected 1H, 13C heteronuclear multiple-bond connectivity (HMBC) experiments, the following structure of the O-specific polysaccharide of Proteus penneri strain 25 was established: [formula: see text] where D-GlcN(L-Ala) is 2-(L-alanylamido)-2-deoxy-D-glucose.

Acetylation↗