Structural analysis of the specific capsular polysaccharide of Streptococcuspneumoniae type 22F

1989 ◽  
Vol 67 (6) ◽  
pp. 1038-1050 ◽  
Author(s):  
James C. Richards ◽  
Malcolm B. Perry ◽  
Peter J. Kniskern
Keyword(s):  
Capsular Polysaccharide ◽  
Glucuronic Acid ◽  
Periodate Oxidation ◽  
Resonance Spectroscopy ◽  
Methylation Analysis ◽  
Chemical Shift Correlation ◽  
Structure Formula ◽  
Correlation Techniques ◽  
Heteronuclear Chemical Shift ◽  
C Nmr

The structure of the specific capsular polysaccharide produced by Streptococcuspneumoniae type 22F (American type 22) was investigated by high-field 1H and 13C nuclear magnetic resonance spectroscopy, composition, methylation analysis, and periodate oxidation studies. The polysaccharide was found to be a high molecular weight acidic polymer composed of D-glucose, D-galactose, D-glucuronic acid, and L-rhamnose residues to form a regular repeating hexasaccharide unit having the structure[Formula: see text]in which the β-L-rhamnopyranosyl residues were substituted by O-acetyl groups in 80% of the repeating units. The 1H and 13C nmr resonances of the O-deacetylated type 22F polysaccharide were completely assigned by application of two-dimensional homo- and heteronuclear chemical shift correlation techniques. Keywords: Streptococcuspneumoniae polysaccharide, NMR analysis.

The acidic specific capsular polysaccharide of Rhodococcusequi serotype 3. Structural elucidation and stereochemical analysis of the lactate ether and pyruvate acetal substituents

1992 ◽  
Vol 70 (10) ◽  
pp. 2664-2676 ◽  
Author(s):  
Wayne B. Severn ◽  
James C. Richards
Keyword(s):  
Molecular Weight ◽  
Capsular Polysaccharide ◽  
Glucuronic Acid ◽  
Chemical Shift Correlation ◽  
Stereochemical Analysis ◽  
The Absolute ◽  
Absolute Chirality ◽  
Heteronuclear Chemical Shift ◽  
C Nmr

The specific capsular polysaccharide produced by Rhodococcusequi serotype 3 was found to be a high-molecular-weight acidic polymer composed of D-glucose, D-galactose, D-glucuronic acid, 4-O-[(S)-1-carboxyethyl]-D-mannose, and pyruvic acid in equal molar proportions. Structural analysis, employing a combination of chemical and nuclear magnetic resonance techniques, established that the polysaccharide is composed of linear repeating tetrasaccharide units,[Formula: see text]in which (R)-1-carboxyethylidene groups bridge the O-2 and O-3 positions of the β-D-glucuronic acid residues. The 1H and 13C NMR resonances of the native and depyruvulated serotype 3 polysaccharides were fully assigned by homo- and heteronuclear chemical shift correlation methods. The absolute configurations of the lactate-substituted mannopyranosyl residues and the pyruvate acetals were determined from 1H–1H NOE measurements on the intact polysaccharide. Unequivocal determination of the absolute chirality of the 4-O-[(S)-1-carboxyethyl]-β-D-mannopyranose residues was achieved by 1H–1H NOE measurements on an acetylated lactone derivative of the glycose.

Structure of the acidic capsular polysaccharide of Cryptococcus laurentii (NRRL Y-1401)

1982 ◽  
Vol 60 (2) ◽  
pp. 124-130 ◽  
Author(s):  
Malcolm B. Perry ◽  
Ann C. Webb
Keyword(s):  
Molecular Weight ◽  
Capsular Polysaccharide ◽  
Glucuronic Acid ◽  
Optical Rotation ◽  
Periodate Oxidation ◽  
Regular Structure ◽  
Cryptococcus Laurentii ◽  
Partial Acid Hydrolysis ◽  
Magnetic Resonance Studies ◽  
Structure Formula

The capsular polysaccharide produced by Cryptococcus laurentii (NRRL Y-1401) is composed of D-mannose (3 mol), D-glucuronic acid (1 mol), D-xylose (1 mol), and O-acetyl (~1 mol). Methylation, periodate oxidation, partial acid hydrolysis, optical rotation, and nuclear magnetic resonance studies showed that the polysaccharide is a high molecular weight branched polymer of regular structure having a repeating pentasaccharide unit with the structure:[Formula: see text]

Structural analysis of the specific polysaccharide of Streptococcus pneumoniae type 9L (American type 49)

1984 ◽  
Vol 62 (12) ◽  
pp. 1309-1320 ◽  
Author(s):  
James C. Richards ◽  
Malcolm B. Perry ◽  
Peter J. Kniskern
Keyword(s):  
Streptococcus Pneumoniae ◽  
Nitrous Acid ◽  
Capsular Polysaccharide ◽  
Glucuronic Acid ◽  
Optical Rotation ◽  
Periodate Oxidation ◽  
Part D ◽  
Partial Acid Hydrolysis ◽  
Specific Polysaccharide ◽  
Structure Formula

The specific capsular polysaccharide produced by Streptococcus pneumoniae type 9L (American type 49) is composed of D-galactose (one part), D-glucose (one part), D-glucuronic acid (one part), 2-acetamido-2-deoxy-D-mannose (one part) and 2-acetamido-2-deoxy-D-glucose (one part). Partial acid hydrolysis, periodate oxidation, nitrous acid deamination, optical rotation, methylation and 13C and 1H nuclear magnetic resonance studies showed that the polysaccharide is an unbranched high molecular weight linear polymer of a repeating pentasaccharide unit having the structure:[Formula: see text]

Glucan isolated from leaves of Althaea officinalis L.

1983 ◽  
Vol 48 (7) ◽  
pp. 2082-2087 ◽  
Author(s):  
Alžbeta Kardošová ◽  
Jozef Rosík ◽  
Rudolf Toman ◽  
Peter Capek
Keyword(s):  
Medicinal Plant ◽  
Periodate Oxidation ◽  
Linear Structure ◽  
Water Soluble ◽  
Partial Hydrolysis ◽  
Methylation Analysis ◽  
Glycosidic Bonds ◽  
Nmr Data ◽  
Althaea Officinalis ◽  
C Nmr

A water-soluble low-molecular D-glucan was isolated from leaves of the medicinal plant marsh-mallow (Althaea officinalis L.). The results of methylation analysis, partial hydrolysis, periodate oxidation, and 13C NMR data indicated a virtually linear structure with α-(1→6) glycosidic bonds.

Structural studies of the capsular polysaccharide from Streptococcus pneumoniae Type 12F

1981 ◽  
Vol 59 (14) ◽  
pp. 2081-2085 ◽  
Author(s):  
Karin Leontein ◽  
Bengt Lindberg ◽  
Jörgen Lönngren
Keyword(s):  
Streptococcus Pneumoniae ◽  
Nmr Spectroscopy ◽  
Capsular Polysaccharide ◽  
Structural Studies ◽  
Methylation Analysis ◽  
Mannuronic Acid ◽  
Structure Formula

The capsular polysaccharide from Streptococcus pneumoniae type 12F is composed of D-glucosyl, D-galactosyl, 2-acetamido-2-deoxy-D-galactosyl, 2-acetamido-2,6-dideoxy-L-galactosyl, and 2-acetamido-2-deoxy-D-mannuronic acid residues in the proportions 2:1:1:1:1. The main structural evidence was adduced from nmr spectroscopy, methylation analysis, and specific degradations whereby it could be concluded that the polysaccharide is composed of hexasaccharide repeating-units having the structure:[Formula: see text]

The specific capsular polysaccharide of Streptococcus pneumoniae type 15A (American type 30)

1984 ◽  
Vol 62 (2-3) ◽  
pp. 151-161 ◽  
Author(s):  
Martine Caroff ◽  
Malcolm B. Perry
Keyword(s):  
Molecular Weight ◽  
Nuclear Magnetic Resonance ◽  
Streptococcus Pneumoniae ◽  
Magnetic Resonance ◽  
High Molecular Weight ◽  
Capsular Polysaccharide ◽  
Optical Rotation ◽  
Periodate Oxidation ◽  
Magnetic Resonance Studies ◽  
Structure Formula

The specific capsular polysaccharide of Streptococcus pneumoniae type 15A (American type 30) is composed of D-galactose (three parts), D-glucose (one part), 2-acetamido-2-deoxy-D-glucose (one part), phosphate (one part), and glycerol (one part). Hydrolysis, periodate oxidation, methylation, optical rotation, and nuclear magnetic resonance studies showed that the polysaccharide is a high molecular weight linear polymer of a pentasaccharide repeating unit having the structure:[Formula: see text]

scholarly journals Characterization of the Antigenic Lipopolysaccharide O Chain and the Capsular Polysaccharide Produced by Actinobacillus pleuropneumoniae Serotype 13

2004 ◽  
Vol 72 (10) ◽  
pp. 5925-5930 ◽  
Author(s):  
Leann L. MacLean ◽  
Malcolm B. Perry ◽  
Evguenii Vinogradov
Keyword(s):  
Capsular Polysaccharide ◽  
Teichoic Acid ◽  
Periodate Oxidation ◽  
Actinobacillus Pleuropneumoniae ◽  
Antigenic Specificity ◽  
Resonance Spectroscopy ◽  
Type I ◽  
Specific Chemical ◽  
Chemical Structures ◽  
Acid Type

ABSTRACT Serotyping of Actinobacillus pleuropneumoniae, the etiologic agent of porcine pleuropneumonia, is important for epidemiological studies and for the development of homologous vaccine cell preparations. The serology is based on the specific chemical structures of capsular polysaccharides (CPSs) and lipopolysaccharide (LPS) antigenic O-polysaccharide moieties (O-PSs), and knowledge of these structures is required for a molecular-level understanding of their serological specificities. The structures of A. pleuropneumoniae serotype 1 to 12 CPSs and O-PSs have been elucidated; however, the structures associated with three newly proposed serotypes (serotypes 13, 14, and 15) have not been reported. Herein we described the structures of the antigenic O-PS and CPS of A. pleuropneumoniae serotype 13. The O-PS of the A. pleuropneumoniae serotype 13 LPS is a polymer of branched tetrasaccharide repeating units composed of l-rhamnose, 2-acetamido-2-deoxy-d-galactose, and d-galactose residues (1:1:2). By use of hydrolysis, methylation, and periodate oxidation chemical methods together with the application of one- and two-dimensional 1H and 13C nuclear magnetic resonance spectroscopy and mass spectrometry, the structures of the O chain and CPS were determined. The CPS of A. pleuropneumoniae serotype 13 was characterized as a teichoic-acid type polymer. The LPS O antigen was identical to the O-PS produced by A. pleuropneumoniae serotype 7. The CPS has the unique structure of a 1,3-poly(glycerol phosphate) teichoic acid type I polymer and constitutes the macromolecule defining the A. pleuropneumoniae serotype 13 antigenic specificity.

Structural characterization of the O-antigenic polysaccharide of Escherichia coli serotype O17 lipopolysaccharide

1996 ◽  
Vol 74 (2) ◽  
pp. 241-248 ◽  
Author(s):  
Hussein Masoud ◽  
Malcolm B. Perry
Keyword(s):  
Escherichia Coli ◽  
Periodate Oxidation ◽  
Resonance Spectroscopy ◽  
Two Dimensional ◽  
High Molecular Weight Polymer ◽  
Molecular Weight Polymer ◽  
Antigenic Polysaccharide ◽  
Structure Formula ◽  
Escherichia Coli Lipopolysaccharide

The structure of the O-poly saccharide component of the lipopolysaccharide produced by Escherichia coli O17 (ATCC 23512) was determined by the use of methylation, periodate oxidation, one- and two-dimensional nuclear magnetic resonance spectroscopy, and mass spectrometric methods. The O-polysaccharide was found to be a high molecular weight polymer of repeating branched pentasaccharide units composed of D-mannose, D-glucose, and 2-acetamido-2-deoxy-D-glucose residues (3:1:1) and had the structure[Formula: see text]Key words: Escherichia coli, lipopolysaccharide, polysaccharide, NMR.

Structure determination ofStreptococcus suisserotype 2 capsular polysaccharide

2010 ◽  
Vol 88 (3) ◽  
pp. 513-525 ◽  
Author(s):  
Marie-Rose Van Calsteren ◽  
Fleur Gagnon ◽  
Sonia Lacouture ◽  
Nahuel Fittipaldi ◽  
Marcello Gottschalk
Keyword(s):  
Sialic Acid ◽  
Capsular Polysaccharide ◽  
Group B Streptococcus ◽  
Periodate Oxidation ◽  
Methylation Analysis ◽  
Mild Acid Hydrolysis ◽  
Chemically Modified ◽  
Group B ◽  
Suis Serotype ◽  
Mild Acid

The capsular polysaccharide (CPS) of Streptococcus suis serotype 2 was isolated, purified, chemically modified, and characterized. Sugar and absolute configuration analyses of the CPS gave the following composition: d-Gal, 3; d-Glc, 1; d-GlcNAc, 1; d-Neu5Ac, 1; l-Rha, 1. Sialic acid was found to be terminal, and the CPS was quantitatively desialylated by mild acid hydrolysis. The CPS was also submitted to periodate oxidation followed by borohydride reduction and Smith degradation. Sugar and methylation analysis,1H and13C nuclear magnetic resonance, and mass spectrometry of the native CPS or of its specifically modified products allowed to determine the repeating unit sequence: [4)[Neu5Ac(α2–6)Gal(β1–4)GlcNAc(β1–3)]Gal(β1–4)[Gal(α1–3)]Rha(β1–4)Glc(β1-]n. The backbone sequence was found to be identical to that of Streptococcus agalactiae or group B Streptococcus (GBS) type VIII and Streptococcus pneumoniae type 23F. The S. suis CPS shares the sequence Neu5Ac-Gal-GlcNAc-Gal in common with GBS types Ia, Ib, II, III, and IV CPSs but differs from them by the presence of rhamnose and the fact that sialic acid is 2,6- rather than 2,3-linked to the following Gal. A correlation between the S. suis CPS sequence and genes of the serotype 2 cps locus encoding putative enzymes responsible for the biosynthesis of the repeating unit was tentatively established.

Structural determination of the O-antigenic polysaccharide of enteropathogenicEscherichia coliO103:H2

2010 ◽  
Vol 56 (5) ◽  
pp. 367-372 ◽  
Author(s):  
Evgeny Vinogradov ◽  
Leann L. MacLean ◽  
Malcolm B. Perry
Keyword(s):  
Periodate Oxidation ◽  
Enterohemorrhagic Escherichia Coli ◽  
Structural Determination ◽  
Two Dimensional ◽  
Methylation Analysis ◽  
Polysaccharide Antigen ◽  
Antigenic Polysaccharide ◽  
Oxidation Degradation ◽  
C Nmr

The structure of the antigenic O-polysaccharide isolated from the lipopolysaccharide produced by enterohemorrhagic Escherichia coli O103:H2 was determined and shown to be composed of d-glucose (1 part), 2-acetamido-2-deoxy-d-glucose (2 parts), 2-acetamido-2-deoxy-d-galactose (1 part), and 3-deoxy-3-(R)-3-hydroxybutyramido-d-fucose (1 part). From the results of methylation analysis, Smith-type periodate oxidation degradation studies, and the use of one- and two-dimensional1H and13C NMR spectroscopy, the O-polysaccharide antigen was found to be an unbranched polymer of a repeating pentasaccharide unit having the following structure: →2)-β-d-Glcp-(1→2)-β-d-Fucp3NBu-(1→6)-α-d-GlcpNAc-(1→4)-α-d-GalpNAc-(1→3)-β-d-GlcpNAc-(1→, where Bu is (R)-3-hydroxybutyramido.

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