URONIC ACIDS FROM WHITE SPRUCE (PICEA GLAUCA (MOENCH) VOSS)

1959 ◽  
Vol 37 (1) ◽  
pp. 29-34 ◽  
Author(s):  
G. A. Adams
Keyword(s):  
Acid Hydrolysis ◽  
Picea Glauca ◽  
Glucuronic Acid ◽  
White Spruce ◽  
Uronic Acids ◽  
Spruce Wood ◽  
Acidic Sugars ◽  
Hydrolysis Of ◽  
Acidic Components

Acid hydrolysis of extractive-free white spruce wood produced a number of neutral and acidic sugars and oligosaccharides. The acidic components were isolated and three of these were shown to be 4-O-methyl-D-glucuronic acid, 2-O-(4-O-methyl-α-D-glucopyranosyluronic acid)-D-xylose, and tentatively O-(4-O-methyl-α-D-glucopyranosyluronic acid)-(1→ 2)-O-β-D-xylopyranosyl-(1→ 4)-D-xylopyranose.

STRUCTURE OF AN ARABOGALACTAN FROM WHITE SPRUCE (PICEA GLAUCA (MOENCH) VOSS)

1958 ◽  
Vol 36 (5) ◽  
pp. 755-762 ◽  
Author(s):  
G. A. Adams
Keyword(s):  
Picea Glauca ◽  
Periodate Oxidation ◽  
White Spruce ◽  
Water Soluble ◽  
Molar Ratio ◽  
Glycosidic Bonds ◽  
Spruce Wood ◽  
Soluble Polysaccharide ◽  
Branched Structure ◽  
Hydrolysis Of

A water-soluble polysaccharide isolated from white spruce wood contained D-galactose, L-arabinose, and D-xylose in a molar ratio of 21:3:1. Hydrolysis of the fully methylated polysaccharide yielded 2,3,5-tri-O-methyl-L-arabinose (12 moles); 2,3,4,6-tetra-O-methyl-D-galactose (29 moles); 2,3,4-tri-O-methyl-D-galactose (34 moles); 2,6-di-O-methyl-D-galactose (0.5 moles); 2,4-di-O-methyl-D-galactose (45 moles); 2,3-di-O-methyl-D-xylose (5 moles); and monomethyl xylose (1 mole). When oxidized by periodate the polysaccharide consumed 1.18 moles of oxidant, and yielded 0.56 moles of formic acid per mole of anhydro-D-galactose. The D-xylose was attributed to the presence of a xylan mixed with the arabogalactan in the original polysaccharide preparation. The methylation and periodate oxidation data showed that the arabogalactan possessed a highly branched structure with the anhydro-D-galactose units being joined by 1 → 3 and 1 → 6 glycosidic bonds. All of the L-arabinose was present in the furanoside form as non-reducing terminal units.

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.

CONSTITUTION OF A DEGRADED POLYSACCHARIDE FROM WHEAT BRAN

1957 ◽  
Vol 35 (2) ◽  
pp. 108-114 ◽  
Author(s):  
J. Schmorak ◽  
C. T. Bishop ◽  
G. A. Adams
Keyword(s):  
Acid Hydrolysis ◽  
Wheat Bran ◽  
Glucuronic Acid ◽  
Periodate Oxidation ◽  
Glycosidic Bond ◽  
Cellulolytic Enzyme ◽  
Acidic Polysaccharide ◽  
Hydrolysis Of ◽  
End Group ◽  
Acid Unit

Graded acid hydrolysis of a soluble wheat bran hemicellulose containing L-arabinose (50%), D-xylose (38.5%), and D-glucuronic acid (9.0%) preferentially removed the L-arabinose giving an insoluble acidic polysaccharide in approximately 25% yield by weight. Methylation studies, periodate oxidation data, and hypoiodite end group estimations showed that the degraded polysaccharide was composed of repeating units of 7-8 D-xylopyranose residues joined by β,1 → 4 linkages. To this repeating unit, one D-glucuronic acid unit was attached by a 1 → 2 glycosidic bond. The cellulolytic enzyme of Myrotheciumverrucaria, which is specific for β,1 → 4 glycosidic linkages, hydrolyzed the degraded polysaccharide although it had no effect on the parent hemicellulose

scholarly journals Synthesis, characterization and properties of uridine 5′-(α-d-apio-d-furanosyl pyrophosphate)

1973 ◽  
Vol 133 (2) ◽  
pp. 227-241 ◽  
Author(s):  
P. K. Kindel ◽  
R. R. Watson
Keyword(s):  
Acid Hydrolysis ◽  
Half Life ◽  
Glucuronic Acid ◽  
Chemical Characterization ◽  
Paper Electrophoresis ◽  
Alkaline Degradation ◽  
Reaction Products ◽  
Starting Compound ◽  
Cyclic Phosphate ◽  
Hydrolysis Of

1. A method was developed for synthesizing UDP-apiose [uridine 5′-(α-d-apio-d-furanosyl pyrophosphate)] from UDP-glucuronic acid [uridine 5′-(α-d-glucopyranosyluronic acid pyrophosphate)] in 62% yield with the enzyme UDP-glucuronic acid cyclase. 2. UDP-apiose had the same mobility as uridine 5′-(α-d-xylopyranosyl pyrophosphate) when chromatographed on paper and when subjected to paper electrophoresis at pH5.8. When [3H]UDP-[U-14C]glucuronic acid was used as the substrate for UDP-glucuronic acid cyclase, the 3H/14C ratio in the reaction product was that expected if d-apiose remained attached to the uridine. In separate experiments doubly labelled reaction product was: (a) hydrolysed at pH2 and 100°C for 15min; (b) degraded at pH8.0 and 100°C for 3min; (c) used as a substrate in the enzymic synthesis of [14C]apiin. In each type of experiment the reaction products were isolated and identified and were found to be those expected if [3H]UDP-[U-14C]apiose was the starting compound. 3. Chemical characterization established that the product containing d-[U-14C]apiose and phosphate formed on alkaline degradation of UDP-[U-14C]apiose was α-d-[U-14C]apio-d-furanosyl 1:2-cyclic phosphate. 4. Chemical characterization also established that the product containing d-[U-14C]apiose and phosphate formed on acid hydrolysis of α-d-[U-14C]apio-d-furanosyl 1:2-cyclic phosphate was d-[U-14C]apiose 2-phosphate. 5. The half-life periods for the degradation of UDP-[U-14C]apiose to α-d-[U-14C]apio-d-furanosyl 1:2-cyclic phosphate and UMP at pH8.0 and 80°C, at pH8.0 and 25°C and at pH8.0 and 4°C were 31.6s, 97.2min and 16.5h respectively. The half-life period for the hydrolysis of UDP-[U-14C]-apiose to d-[U-14C]apiose and UDP at pH3.0 and 40°C was 4.67min. After 20 days at pH6.2–6.6 and 4°C, 17% of the starting UDP-[U-14C]apiose was degraded to α-d-[U-14C]apio-d-furanosyl 1:2-cyclic phosphate and UMP and 23% was hydrolysed to d-[U-14C]apiose and UDP. After 120 days at pH6.4 and −20°C 2% of the starting UDP-[U-14C]apiose was degraded and 4% was hydrolysed.

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.

THE POLYSACCHARIDE PRODUCED BY AZOTOBACTER INDICUM

1957 ◽  
Vol 3 (2) ◽  
pp. 277-288 ◽  
Author(s):  
Clara M. Quinnell ◽  
S. G. Knight ◽  
P. W. Wilson
Keyword(s):  
Acid Hydrolysis ◽  
Paper Chromatography ◽  
Uronic Acid ◽  
Glucuronic Acid ◽  
Relative Proportion ◽  
Infrared Analysis ◽  
Uronic Acids ◽  
Pyranose Form ◽  
Isolation And Purification ◽  
A Value

A procedure was developed for the isolation and purification of the polysaccharide produced by Azotobacter indicum which resulted in a product containing approximately 5% ash, 0.4–0.6% nitrogen, and 40% carbon. Qualitative tests showed the absence of galactose, pentoses, ketoses, and amino and methylated sugars, and the presence of glucose and a uronic acid. A technique for determining combined uronic acids resulted in a value of 30% uronic acid on the untreated (unhydrolyzed) polysaccharide, and the remaining components were determined by analysis of the material after acid hydrolysis. The relatively severe conditions required to hydrolyze the polysaccharide indicate that the components are present in the pyranose form. The results obtained when the hydrolyzates were analyzed by paper chromatography, the spectrophotometric reactions of Dische, and other specific quantitative assays showed that the polysaccharide is a polymer of glucose, glucuronic acid, and an aldoheptose in the ratio of 3: 2: 1. Infrared analysis confirmed the presence and relative proportion of the uronic acid residues and indicated that the sugar units of the polysaccharide are probably in the beta configuration.

scholarly journals Studies on Medicago lupulina saponins. 5. Isolation and chemical characterization of blossom saponins

2014 ◽  
Vol 56 (1) ◽  
pp. 101-106 ◽  
Author(s):  
Marian Jurzysta ◽  
Stanisław Burda ◽  
Wiesław Oleszek ◽  
Piotr Górski ◽  
Michał Płoszyński
Keyword(s):  
Acid Hydrolysis ◽  
Glucuronic Acid ◽  
Water Solution ◽  
Chemical Characterization ◽  
Medicago Lupulina ◽  
Medicagenic Acid ◽  
Hydrolysis Of

The separation of saponins derived from <em>Medicago lupulina</em> L. flowers yielded two saponin fractions. The first one, made up of crystalline saponins, readily precipitable from water solution, was a mixture of three glycosides of soyasapogenol B. Acid hydrolysis of these saponins yielded soyasapogenol B and its three artifacts: soyasapogenols C. D and F. Xylose, rhamnose, galactose, glucose and glucuronic acid were found as sugar constituents. The second fraction obtained by cholesterol precipitation consisted of seven haemolytically active medicagenic acid glycosides. Their hydrolysis furnished medicagenic acid and glucose, xylose, rhamnose and traces of glucuronic acid.

Polysaccharides of tropical pasture herbage. II. A xylan from the leaf of spear grass (Heteropogon contortus)

1970 ◽  
Vol 23 (11) ◽  
pp. 2361 ◽  
Author(s):  
JD Blake ◽  
GN Richards
Keyword(s):  
Gas Chromatography ◽  
Acid Hydrolysis ◽  
Copper Complex ◽  
Glucuronic Acid ◽  
Single Units ◽  
Alkaline Extraction ◽  
Tropical Pasture ◽  
Fractional Precipitation ◽  
Heteropogon Contortus ◽  
Hydrolysis Of

Alkaline extraction of spear grass holocellulose gave a xylan which was purified by fractional precipitation as a copper complex. Acid hydrolysis yielded L-arabinose, D-xylose, and an aldobiouronic acid consisting of D-xylose and 4-O-methyl-D-glucuronic acid. Hydrolysis of the methylated xylan gave 2,3,5-tri-O-methyl-L- arabinose, 2,3,4-tri-, 2,3-di-, and 2-O-methyl-D-xylose, and 3-O-methyl-2-O-(2,3,4-tri-O-methyl-D-glucopyranosyluronic acid)-D-xylose. The conditions for isolation of the methylated sugars for gas chromatography were investigated with particular reference to difficulties arising from volatility of the tri-O-methyl pentoses. The xylan is composed of chains of 1,4-linked �-D-xylopyranose residues to which are attached single units of L-arabinofuranose at position 3 and 4-O-methyl-D-glucuronic acid at position 2 of the basal residues.

scholarly journals The acid lability of the glycosidic bonds of l-iduronic acid residues in glycosaminoglycans

1980 ◽  
Vol 191 (2) ◽  
pp. 355-363 ◽  
Author(s):  
H E Conrad
Keyword(s):  
Acid Hydrolysis ◽  
Glucuronic Acid ◽  
Heparan Sulphate ◽  
Neutral Sugar ◽  
Uronic Acids ◽  
Dermatan Sulphate ◽  
Glycosidic Bonds ◽  
Iduronic Acid ◽  
Quantitative Analyses ◽  
Kinetics Of

Heparan sulphate, heparin and dermatan sulphate were hydrolysed in 0.5M-H2SO4 at 100 degrees C. At intervals portions of the hydrolysate were removed and treated with HNO2 at pH 4.0 to cleave the glycosidic bonds of the N-unsubstituted hexosamine residues and to convert both free and combined hexosamines into anhydrohexoses. These hydrolysis/deamination mixtures were reduced with NaB3H4 and analysed by radiochromatography for alpha-L-iduronosylanhydrohexose, beta-D-glucuronosylanhydrohexose, and the free uronic acids and anhydrohexose. These data gave a kinetic profile of the cleavage of the alpha-L-iduronosyl and the beta-D-glucuronosyl bonds in these glycosaminoglycans. The beta-D-glucuronosyl bonds showed the expected resistance to acid hydrolysis, but the alpha-L-iduronosyl bonds were found to be as labile to acid as some neutral sugar glycosides. This unusual lability of alpha-D-iduronosyl-anhydromannitol and beta-D-glucuronosylanhydromannitol. The procedures used to follow the kinetics of glycosaminoglycan hydrolysis can also be sued to obtain quantitative analyses of L-iduronic acid, D-glucuronic acid and hexosamine in these polymers.

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