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 Removal of the O-acetyl groups with ammonia gave a compound no longer active towards type 11A antiserum. 3.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.

scholarly journals The type-specific substance from Pneumococcus type 13

1972 ◽  
Vol 130 (1) ◽  
pp. 45-54 ◽  
Author(s):  
M. J. Watson ◽  
Jean M. Tyler ◽  
J. G. Buchanan ◽  
J. Baddiley
Keyword(s):  
Hydroxyl Group ◽  
Partial Structure ◽  
Specific Substance ◽  
Pneumococcus Type

1. The type-specific substance, S.13, from Pneumococcus type 13 was subjected to hydrolysis with alkali, followed by enzymic dephosphorylation, to yield a pentasaccharide. 2. The pentasaccharide, corresponding to the dephosphorylated repeating unit of S.13, was shown to be O-β-d-galactopyranosyl-(1→4)-O-β- d-glucopyranosyl-(1→3)-O-β-d- galactofuranosyl-(1→4)-O-2-acetamido-2-deoxy-β-d- glucopyranosyl-(1→2)-ribitol. 3. The phosphodiester linkages in S.13 join the hydroxyl group at position 1 of ribitol and the hydroxyl group at position 4 of a galactopyranosyl residue in the next repeating unit. 4. Ester groups, presumably O-acetyl, are located on positions 2 or 3 of most glucopyranosyl residues in S.13. 5. A partial structure for S.13 is proposed.

scholarly journals The type-specific substance from Pneumococcus type 29

1969 ◽  
Vol 111 (4) ◽  
pp. 547-556 ◽  
Author(s):  
E. Venkata Rao ◽  
M. J. Watson ◽  
J. G. Buchanan ◽  
J Baddiley
Keyword(s):  
Hydroxyl Group ◽  
Partial Structure ◽  
Galactose Residue ◽  
Specific Substance ◽  
Pneumococcus Type

1. A pentasaccharide, corresponding to the dephosphorylated repeating unit of the specific substance, S.29, from Pneumococcus type 29, was obtained by hydrolysis with alkali followed by enzymic dephosphorylation. 2. The pentasaccharide was shown to be O-2-acetamido-2-deoxy-β-d-galactopyranosyl-(1→6)-O-β-d-galactofuranosyl-(1→3)-O-β-d-galactopyranosyl-(1→6)-O-β-d-galactofuranosyl-(1→1)-ribitol. 3. The phosphodiester linkages in S.29 join the hydroxyl group at position 5 of ribitol and the hydroxyl group at position 3 or 4 of a 2-acetamido-2-deoxy-d-galactose residue in the next repeating unit. 4. A partial structure for S.29 was deduced from these experiments.

scholarly journals The specific substance from Pneumococcus type 34 (41). The phosphodiester linkages

1968 ◽  
Vol 109 (4) ◽  
pp. 597-602 ◽  
Author(s):  
G. J. F. Chittenden ◽  
W. K. Roberts ◽  
J. G. Buchanan ◽  
J Baddiley
Keyword(s):  
Hydroxyl Group ◽  
Partial Structure ◽  
Specific Substance ◽  
Phosphate Groups ◽  
Pneumococcus Type

1. The phosphate groups in the type-specific substance S.34 from Pneumococcus type 34 (U.S. type 41) were shown to join the hydroxyl group at position 1 or 5 of ribitol and the hydroxyl group at position 3 of a d-galactofuranosyl residue in the next repeating unit. 2. A partial structure of the type-specific substance was derived. 3. New syntheses of d-galactose 2-phosphate and d-galactose 3-phosphate are described.

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.

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.

Glucosylation of 5-androsten-3β-ol derivatives containing butenolide, furan or unsaturated ester moieties in the side chain

1984 ◽  
Vol 49 (4) ◽  
pp. 881-891 ◽  
Author(s):  
Ivan Černý ◽  
Vladimír Pouzar ◽  
Pavel Drašar ◽  
Miloš Buděšínský ◽  
Miroslav Havel
Keyword(s):  
Sodium Borohydride ◽  
Lactone Ring ◽  
Acetyl Derivative ◽  
Side Chain ◽  
Unsaturated Ester ◽  
Reaction Sequence ◽  
Silver Silicate

3-O-(Tetra-O-acetyl-β-D-glucopyranosyl) derivatives II, V, XV and XX were prepared from 5-androstene-3β,17β-diol 17-benzoate (I), (20R)-3β-hydroxy-21-nor-5,22-choladien-(24 -20)-olide (IV), 17β-(2-furyl)-5-androsten-3β-ol (XIV) and methyl (20E)-3β-hydroxy-5,20-pregnadiene-21-carboxylate (XIX), respectively, using tetra-O-acetyl-α-D-glucopyranosyl bromide and silver silicate. The furyl derivative XIV was obtained from methyl 3β-methoxymethyletienate VIII by reaction sequence in which the key reactions were alkylation of the keto sulfoxide IX with bromoacetate, cyclization of the obtained product with sodium borohydride and reduction of the mixture of lactones XI and XII with diisobutylaluminium hydride. The unsaturated ester XIX was prepared from 3β-acetoxy-5-androstene-17β-carbaldehyde (XVII) by treatment with diethyl methoxycarbonylmethylphosphonate and deacetylation of the formed acetyl derivative XVIII. Deacetylation of the acetyl derivatives II, XV and XX afforded the glucosides III,XVI and XXI, respectively; the deacetylation of V was accompanied by opening of the lactone ring under formation of the methyl 21-nor-20-oxo-5-cholen-24-oate derivative VI.

Preparation of 3-deoxy-3-fluoro-D-mannose and corresponding hexitol

1983 ◽  
Vol 48 (9) ◽  
pp. 2693-2700 ◽  
Author(s):  
Miloslav Černý ◽  
Jitka Doležalová ◽  
Jindra Mácová ◽  
Josef Pacák ◽  
Tomáš Trnka ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Ethylene Glycol ◽  
Sodium Borohydride ◽  
Acetyl Derivative ◽  
Potassium Fluoride ◽  
H Nmr

Reaction of 1,6 : 3,4-dianhydro-β-D-altropyranose (I) with potassium fluoride in hot ethylene glycol gave 1,6-anhydro-3-deoxy-3-fluoro-β-D-mannopyranose (II). On acid catalysed hydrolysis or acetolysis of compound II 3-deoxy-3-fluoro-D-mannose (VIII) or its tetra-O-acetyl derivative VII, respectively, were obtained. Reduction of compound VIII with sodium borohydride gave 3-deoxy-3-fluoro-D-mannitol (IX). The structures of the mentioned compounds were proved by 1H NMR spectroscopy.

scholarly journals The structure of a glycopeptide purified from porcine thyroglobulin

1971 ◽  
Vol 123 (3) ◽  
pp. 415-420 ◽  
Author(s):  
Minoru Fukuda ◽  
Fujio Egami
Keyword(s):  
Sialic Acid ◽  
Sodium Borohydride ◽  
Periodate Oxidation ◽  
Galactose Oxidase ◽  
Borohydride Reduction ◽  
Enzymic Hydrolysis ◽  
End Groups ◽  
Sodium Borohydride Reduction

1. The structure of a purified glycopeptide isolated from porcine thyroglobulin was studied by sequential hydrolysis with specific glycosidases, by periodate oxidation and by treatment with galactose oxidase. 2. Sequential hydrolysis with several combinations of neuraminidase, α-l-fucosidase, β-d-galactosidase, β-N-acetyl-d-glucosaminidase and α-d-mannosidase presented the evidence for the following structure. 3. The monosaccharide sequence of the peripheral moiety of the heteropolysaccharide chain was sialic acid→galactose→N-acetylglucosamine. Some of the galactose residues were non-reducing end-groups with the sequence galactose→N-acetylglucosamine. 4. After removal of the peripheral moiety composed of sialic acid, fucose, galactose and N-acetylglucosamine, α-mannosidase released 1.4mol of mannose/mol of glycopeptide, indicating that two of the three mannose residues were located between peripheral N-acetylglucosamine and internal N-acetylglucosamine or mannose. 5. Periodate oxidation and sodium borohydride reduction confirmed the results obtained by enzymic degradation and gave information concerning the position of substitution. 6. Based on the results obtained by enzymic hydrolysis and periodate oxidation together with the treatment with galactose oxidase, a structure is proposed for the glycopeptide.

scholarly journals The type-specific substance from Pneumococcus type 33B

1974 ◽  
Vol 137 (3) ◽  
pp. 603-606 ◽  
Author(s):  
M. J. Watson
Keyword(s):  
Total Sugar ◽  
Hydroxyl Groups ◽  
Specific Substance ◽  
Pneumococcus Type

1. The type-specific substance, S. 33B, from Pneumococcus type 33B contains P, 2.89; hexose, 51; total sugar, 69; galactosamine, 18; and d-glucose, 20%. 2. After degradation with alkali, followed by enzymic dephosphorylation, S. 33B yielded a hexasaccharide. 3. The hexasaccharide was assigned the structure O-β-d-glucopyranosyl- (1→5)-O-β-d-galactofuranosyl- (1→3)-O-2-acetamido-2-deoxy-β-d- galactopyranosyl-(1→4)-O-[α-d- galactopyranosyl-(1→2)]-α-d-galactopyranosyl- (1→2)-ribitol. 4. Phosphate residues in S. 33B are located on the hydroxyl groups at position 5 of ribitol units and on the hydroxyl groups at position 6 of hexopyranose residues.

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