EXOCELLULAR BACTERIAL POLYSACCHARIDE FROM XANTHOMONAS CAMPESTRIS NRRL B-1459: PART III. STRUCTURE

1964 ◽  
Vol 42 (6) ◽  
pp. 1261-1269 ◽  
Author(s):  
J. H. Sloneker ◽  
Danute G. Orentas ◽  
Allene Jeanes
Keyword(s):  
Sodium Borohydride ◽  
Xanthomonas Campestris ◽  
Glucuronic Acid ◽  
Periodate Oxidation ◽  
Side Chain ◽  
Bacterial Polysaccharide ◽  
Salt Solutions ◽  
Anomalous Viscosity ◽  
Viscosity Behavior ◽  
Mild Acid

Periodate oxidation showed that the O-acetyl groups in the polysaccharide sterically affected the rate but not the extent of oxidation of the D-mannose residues, two-thirds of which were glycosidically substituted at C2 by a D-glucuronic acid residue and one-third of which was linked as a terminal side-chain residue. The D-glucose and D-glucuronic acid residues oxidized by periodate were substituted at C4, but both were more resistant to oxidation than were the D-mannose residues. One-third of the D-glucose residues and a significant quantity of the D-glucuronic acid residues were inert to vigorous periodate oxidation and may bear side-chain residues. Quantitative recovery of the periodate-stable D-glucose residues as 2-O-β-D-glucopyranosyl-D-erythritol, after the oxidized polysaccharide was reduced with sodium borohydride and hydrolyzed with mild acid, revealed that two-thirds of the D-glucose residues were in pairs linked (β, 1 → 4). The pyruvic acid linkage in the polysaccharide was established as a 4,6-O-1-carboxyethylidene ketal attached to a terminal D-glucose side-chain residue. The structure of the polysaccharide is discussed in relation to its anomalous viscosity behavior in salt solutions.

scholarly journals Studies of the polysaccharide fraction from the lipopolysaccharide of Pseudomonas alcaligenes

1974 ◽  
Vol 139 (3) ◽  
pp. 633-643 ◽  
Author(s):  
James A. Lomax ◽  
George W. Gray ◽  
Stephen G. Wilkinson
Keyword(s):  
Gel Filtration ◽  
Periodate Oxidation ◽  
Side Chain ◽  
Partial Hydrolysis ◽  
Methylation Analysis ◽  
Mild Acid Hydrolysis ◽  
Pseudomonas Alcaligenes ◽  
Crude Polysaccharide ◽  
Hydrolysis Of ◽  
Mild Acid

Studies of the lipopolysaccharide of Pseudomonas alcaligenes strain BR 1/2 were extended to the polysaccharide moiety. The crude polysaccharide, obtained by mild acid hydrolysis of the lipopolysaccharide, was fractionated by gel filtration. The major fraction was the phosphorylated polysaccharide, for which the approximate proportions of residues were; glucose (2), rhamnose (0.7), heptose (2–3), galactosamine (1), alanine (1), 3-deoxy-2-octulonic acid (1), phosphorus (5–6). The heptose was l-glycero-d-manno-heptose. The minor fractions from gel filtration contained free 3-deoxy-2-octulonic acid, Pi and PPi. The purified polysaccharide was studied by periodate oxidation, methylation analysis, partial hydrolysis, and dephosphorylation. All the rhamnose and part of the glucose and heptose occur as non-reducing terminal residues. Other glucose residues are 3-substituted, and most heptose residues are esterified with condensed phosphate residues, possibly in the C-4 position. Free heptose and a heptosylglucose were isolated from a partial hydrolysate of the polysaccharide. The location of galactosamine in the polysaccharide was not established, but either the C-3 or C-4 position appears to be substituted and a linkage to alanine was indicated. In its composition, the polysaccharide from Ps. alcaligenes resembles core polysaccharides from other pseudomonads: no possible side-chain polysaccharide was detected.

THE STRUCTURAL ANALYSIS OF SOME ACIDIC XYLANS BY PERIODATE OXIDATION

1962 ◽  
Vol 40 (2) ◽  
pp. 348-352 ◽  
Author(s):  
G. G. S. Dutton ◽  
A. M. Unrau
Keyword(s):  
Acid Hydrolysis ◽  
Glucuronic Acid ◽  
Periodate Oxidation ◽  
Small Degree ◽  
Degree Of Polymerization ◽  
Borohydride Reduction ◽  
Mild Acid Hydrolysis ◽  
Degree Of Branching ◽  
Hydrolysis Of ◽  
Mild Acid

By determining the amount of formaldehyde produced on periodate oxidation of borohydride-reduced apple- and cherry-wood xylans the degree of polymerization was shown to be 155 and 100 respectively. Acid hydrolysis of the polyols obtained by periodate oxidation and borohydride reduction gave ethylene glycol in amounts indicating that these xylans have a small degree of branching. Mild acid hydrolysis of the polyols demonstrated that in these xylans D-glucuronic acid as well as 4-O-methyl-D-glucuronic acid was present and that some of the former occupied non-terminal positions.

Structure determination ofStreptococcus suisserotype 14 capsular polysaccharide

2013 ◽  
Vol 91 (2) ◽  
pp. 49-58 ◽  
Author(s):  
Marie-Rose Van Calsteren ◽  
Fleur Gagnon ◽  
Cynthia Calzas ◽  
Guillaume Goyette-Desjardins ◽  
Masatoshi Okura ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Capsular Polysaccharide ◽  
Group B Streptococcus ◽  
Periodate Oxidation ◽  
Side Chain ◽  
Chemically Modified ◽  
Type Ia ◽  
Group B ◽  
Suis Serotype ◽  
Mild Acid

The capsular polysaccharide (CPS) of Streptococcus suis serotype 14 was purified, chemically modified, and characterized. Sugar and absolute configuration analyses gave the following CPS composition: d-Gal, 3; d-Glc, 1; d-GlcNAc, 1; d-Neu5Ac, 1. The Sambucus nigra lectin, which recognizes the Neu5Ac(α2–6)Gal/GalNAc sequence, showed binding to the native CPS. Sialic acid was found to be terminal, and the CPS was quantitatively desialylated by mild acid hydrolysis. It was also submitted to periodate oxidation followed by borohydride reduction and Smith degradation. Sugar and methylation analyses,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: [6)[Neu5Ac(α2–6)Gal(β1–4)GlcNAc(β1–3)]Gal(β1–3)Gal(β1–4)Glc(β1–]n. S. suis serotype 14 CPS has an identical sialic acid-containing side chain as serotype 2 CPS, but differs by the absence of rhamnose in its composition. The same side chain is also present in group B Streptococcus type Ia CPS, except that in the latter sialic acid is 2,3- rather than 2,6-linked to the following galactose. A correlation between the S. suis CPS sequence and genes of the serotype 14 cps locus encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit is proposed.

EXOCELLULAR BACTERIAL POLYSACCHARIDE FROM XANTHOMONAS CAMPESTRIS NRRL B-1459: PART I. CONSTITUTION

1962 ◽  
Vol 40 (11) ◽  
pp. 2066-2071 ◽  
Author(s):  
J. H. Sloneker ◽  
Allene Jeanes
Keyword(s):  
Acid Hydrolysis ◽  
Pyruvic Acid ◽  
Potassium Salt ◽  
Xanthomonas Campestris ◽  
Glucuronic Acid ◽  
Solution Viscosity ◽  
Bacterial Polysaccharide ◽  
Partial Acid Hydrolysis ◽  
Acid Stable ◽  
End Group

Polysaccharide B-1459 is the first bacterial polysaccharide reported to contain pyruvic acid as a constituent. The polysaccharide, isolated as the potassium salt, was shown to be composed of D-glucose, D-mannose, and D-glucuronic acid, acetic acid, and pyruvic acid in the ratio 2.8:3.0:2.0:1.7:0.51–0.63. One-third of the total mannose was released readily as free mannose by graded acid hydrolysis with only a slow loss of the high solution viscosity. The remainder of the mannose was isolated as the acid-stable aldobiouronic acid 2-O-(β-D-glucopyranosyluronic acid)-D-mannose. Partial acid hydrolysis and preparative paper chromatography afforded two higher oligosaccharides: an aldotriouronic acid composed of glucuronic acid β-linked 1,2 to mannose with glucose as the reducing end group, and what appears to be an aldotetraouronic acid composed of glucuronic acid, mannose, and glucose.

scholarly journals Structural studies on heparan sulphate from human lung fibroblasts. Characterization of oligosaccharides obtained by selective periodate oxidation of d-glucuronic acid residues followed by scission in alkali

1980 ◽  
Vol 191 (1) ◽  
pp. 103-110 ◽  
Author(s):  
Ingrid Sjöberg ◽  
Lars-Ȧke Fransson
Keyword(s):  
Uronic Acid ◽  
Glucuronic Acid ◽  
Human Lung ◽  
General Structure ◽  
Heparan Sulphate ◽  
Periodate Oxidation ◽  
Exchange Chromatography ◽  
Lung Fibroblasts ◽  
Human Lung Fibroblasts ◽  
Iduronic Acid

1. 3H- and 35S-labelled heparan sulphate was isolated from monolayers of human lung fibroblasts and subjected to degradations by (a) deaminative cleavage and (b) periodate oxidation/alkaline elimination. Fragments were resolved by gel- and ion-exchange-chromatography. 2. Deaminative cleavage of the radioactive glycan afforded mainly disaccharides with a low content of ester-sulphate and free sulphate, indicating that a large part (approx. 80%) of the repeating units consisted of uronosyl-glucosamine-N-sulphate. Blocks of non-sulphated [glucuronosyl-N-acetyl glucosamine] repeats (3–4 consecutive units) accounted for the remainder of the chains. 3. By selective oxidation of glucuronic acid residues associated with N-acetylglucosamine, followed by scission in alkali, the radioactive glycan was degraded into a series of fragments. The glucuronosyl-N-acetylglucosamine-containing block regions yielded a compound N-acetylglucosamine–R, where R is the remnant of an oxidized and degraded glucuronic acid. Periodate-insensitive uronic acid residues were recovered in saccharides of the general structure glucosamine–(uronic acid–glucosamine)n–R. 4. Further degradations of these saccharides via deaminative cleavage and re-oxidations with periodate revealed that iduronic acid may be located in sequences such as glucosamine-N-sulphate→iduronic acid→N-acetylglucosamine. Occasionally the iduronic acid was sulphated. Blocks of iduronic acid-containing repeats may contain up to five consecutive units. Alternating arrangements of iduronic acid- and glucuronic acid-containing repeats were also observed. 5. 3H- and 35S-labelled heparan sulphates from sequential extracts of fibroblasts (medium, EDTA, trypsin digest, dithiothreitol extract, cell-soluble and cell-insoluble material) afforded similar profiles after both periodate oxidation/alkaline elimination and deaminative cleavage.

STRUCTURE OF THE EXTRACELLULAR POLYSACCHARIDE PRODUCED BY XANTHOMONAS ORYZAE

1962 ◽  
Vol 40 (12) ◽  
pp. 2204-2213 ◽  
Author(s):  
A. Misaki ◽  
S. Kirkwood ◽  
J. V. Scaletti ◽  
F. Smith
Keyword(s):  
Acid Hydrolysis ◽  
Glucuronic Acid ◽  
Periodate Oxidation ◽  
Extracellular Polysaccharide ◽  
Xanthomonas Oryzae ◽  
Sodium Borohydride Reduction ◽  
Glycoside Hydrolysis ◽  
Hydrolysis Of ◽  
Structural Significance ◽  
Molecular Proportion

The extracellular polysaccharide isolated from cultures of Xanthomonas oryzae is composed of D-glucose (5 molecular proportions), D-glucuronic acid (2 molecular proportions), and D-mannose (5 molecular proportions). Acid hydrolysis of this polysaccharide, which contains 0.3% combined pyruvic acid, yields 2-O-β-D-glucopyranosyluronic acid D-mannose, which has been characterized as its crystalline fully methylated β-glycoside. Hydrolysis of the methylated polysaccharide gives 2,3,4,6-tetra-O-methyl-D-mannose (3 molecular proportions), 2,3,4-tri-O-methyl-D-glucuronic acid (1 molecular proportion), 2,3,6-tri-O-methyl-D-glucose (4 molecular proportions), 3,4,6-tri-O-methyl-D-mannose (2 molecular proportions), 2,6-di-O-methyl-D-glucose (3 molecular proportions), 2,3-di-O-methyl-D-glucose (1 molecular proportion). The polyalcohol derived from the polysaccharide by periodate oxidation followed by sodium borohydride reduction gives upon acid hydrolysis glycerol (2 molecular proportions), erythritol (1 molecular proportion), and D-glucose (1 molecular proportion). The general structural significance of these findings is discussed.

scholarly journals The type-specific substance from Pneumococcus type 11A(43)

1969 ◽  
Vol 115 (1) ◽  
pp. 37-45 ◽  
Author(s):  
D. A. Kennedy ◽  
J. G. Buchanan ◽  
J Baddiley
Keyword(s):  
Sodium Borohydride ◽  
Periodate Oxidation ◽  
Acetyl Derivative ◽  
Partial Structure ◽  
Glycerol Phosphate ◽  
Specific Substance ◽  
Pneumococcus Type

1. The type-specific substance from Pneumococcus type 11A(43) is a polymer containing d-glucose, d-galactose, glycerol, phosphate and O-acetyl in the approximate molecular proportions 2:2:1:1:2. 2. Removal of the O-acetyl groups with ammonia gave a compound no longer active towards type 11A antiserum. 3. Treatment of S.11A with sodium borohydride, followed by hydrolysis with alkali yielded a phosphorus-free polysaccharide, whose structure was studied by methylation and by degradation with periodate. 4. Examination of S.11A and its de-O-acetyl derivative by periodate oxidation led to the partial structure (XI) for the type-specific substance, which thus has several features in common with S.18.

Anomalous viscosity behavior of polymer solutions at very low concentrations

1957 ◽  
Vol 26 (113) ◽  
pp. 213-226 ◽  
Author(s):  
Tōru Kawai ◽  
Kazuhisa Saito ◽  
W. R. Krigbaum
Keyword(s):  
Polymer Solutions ◽  
Anomalous Viscosity ◽  
Viscosity Behavior ◽  
Low Concentrations

Colorimetric assay of glycoprotein glycation free of interference from glycosylation residues

1993 ◽  
Vol 39 (11) ◽  
pp. 2309-2311 ◽  
Author(s):  
D M Kennedy ◽  
A W Skillen ◽  
C H Self
Keyword(s):  
Sodium Borohydride ◽  
Serum Proteins ◽  
Colorimetric Assay ◽  
Periodate Oxidation ◽  
Borohydride Reduction ◽  
Glycan Chain

Abstract We have developed a colorimetric assay for determining the degree of glycation of serum proteins that is unaffected by glycosylation residues. This was accomplished by reducing the proteins with sodium borohydride prior to periodate oxidation. Previous periodate-based methods, which offer several advantages over other glycation assays, cannot determine glycoprotein glycation because interference from sialic residues in the glycan chain can lead to overestimation of the amount of glycation products. Without reduction, glycation of fetuin was double that of asialofetuin glycated under identical conditions. We found that borohydride reduction before periodate oxidation increases the amount of formaldehyde released in proportion to the extent of glycation, irrespective of the degree of glycosylation. Using two glycoproteins and an unglycosylated protein, we showed how measurement of the formaldehyde increase enables the extent of glycoprotein glycation to be determined without removal of interfering sugars.

4,6-O-(1-Carboxyethylidene)-D-mannose as a Structural Unit in Capsular Polysaccharide of Klebsiella K-type 5

1972 ◽  
Vol 50 (14) ◽  
pp. 2382-2384 ◽  
Author(s):  
G. G. S. Dutton ◽  
M. T. Yang
Keyword(s):  
Experimental Data ◽  
Structural Unit ◽  
Capsular Polysaccharide ◽  
Periodate Oxidation ◽  
Side Chain ◽  
Partial Hydrolysis ◽  
Acetyl Group

Methylation, periodate oxidation, and partial hydrolysis techniques have each been used to demonstrate the presence of 4,6-O-(1-carboxyethylidene)-D-mannopyranosyl units in the capsular polysaccharide of Klebsiella K-type 5. The structure of this polysaccharide differs from those known for other Klebsiella capsules by the lack of any carbohydrate side chain. A repeating unit of[Formula: see text](plus one unassigned O-acetyl group) is in accord with the experimental data.

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