STRUCTURE OF THE EXTRACELLULAR POLYSACCHARIDE PRODUCED BY XANTHOMONAS ORYZAE

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.

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CONSTITUTION OF A DEGRADED POLYSACCHARIDE FROM WHEAT BRAN

Canadian Journal of Chemistry ◽

10.1139/v57-017 ◽

1957 ◽

Vol 35 (2) ◽

pp. 108-114 ◽

Cited By ~ 17

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

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THE STRUCTURAL ANALYSIS OF SOME ACIDIC XYLANS BY PERIODATE OXIDATION

Canadian Journal of Chemistry ◽

10.1139/v62-053 ◽

1962 ◽

Vol 40 (2) ◽

pp. 348-352 ◽

Cited By ~ 13

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.

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

Canadian Journal of Chemistry ◽

10.1139/v59-006 ◽

1959 ◽

Vol 37 (1) ◽

pp. 29-34 ◽

Cited By ~ 9

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.

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IMMUNOCHEMICAL STUDIES ON BLOOD GROUPS

Journal of Experimental Medicine ◽

10.1084/jem.133.1.39 ◽

1971 ◽

Vol 133 (1) ◽

pp. 39-52 ◽

Cited By ~ 101

Author(s):

Ten Feizi ◽

Elvin A. Kabat ◽

Giuseppe Vicari ◽

Byron Anderson ◽

W. Laurence Marsh

Keyword(s):

Acid Hydrolysis ◽

Blood Group ◽

Ovarian Cyst ◽

Periodate Oxidation ◽

Human Saliva ◽

Mild Acid Hydrolysis ◽

Group B ◽

Hydrolysis Of ◽

Substantial Heterogeneity ◽

Mild Acid

A partially purified blood group-like substance obtained from milk showed I activity with 2 of 21 anti-I sera. With these antisera, certain human ovarian cyst substances considered to be precursors of the A, B, H, Lea, and Leb substances also showed I activity comparable to the milk material. Strong I activity could be produced by one-stage periodate oxidation and Smith degradation of human ovarian cyst A and B substances, or of hog mucin A + H substance, or by mild acid hydrolysis of human saliva or ovarian cyst blood group B substance. The two sera indicate that I specificity appears at intermediate stages in the biosynthesis of the A, B, H, Lea, and Lea substances. Anti-I sera differ strikingly in their specificities, indicating substantial heterogeneity of the I determinants.

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THE WATER-SOLUBLE POLYSACCHARIDES OF DERMATOPHYTES: III. A GALACTOMANNAN FROM TRICHOPHYTON INTERDIGITALE

Canadian Journal of Chemistry ◽

10.1139/v64-423 ◽

1964 ◽

Vol 42 (12) ◽

pp. 2862-2871 ◽

Cited By ~ 20

Author(s):

F. Blank ◽

M. B. Perry

Keyword(s):

Formic Acid ◽

Acid Hydrolysis ◽

Copper Complex ◽

Periodate Oxidation ◽

Water Soluble ◽

Mild Acid Hydrolysis ◽

Trichophyton Interdigitale ◽

Soluble Polysaccharide ◽

Hydrolysis Of ◽

Mild Acid

The water-soluble polysaccharide preparation from Trichophytoninterdigitale was fractionated to give two distinct galactomannans and a glucan. A galactomannan isolated via its insoluble copper complex had [α]D +75° (water) and was composed of D-galactose (12%) and D-mannose (88%). On periodate oxidation, the galactomannan consumed 1.73 mole periodate and released 0.67 mole formic acid and 0.12 mole formaldehyde per anhydrohexose unit. Hydrolysis of the methylated galactomannan gave 2,3,5,6-tetra-O-methyl-D-galactose (1 part), 2,3,4,6-tetra-O-methyl-D-mannose (1 part), 2,3,4-tri-O-methyl-D-mannose (4 parts), and3,4-di-O-methyl-D-mannose (2 parts). Mild acid hydrolysis of the galactomannan removed all the galactose residues, leaving a mannan having [α]D +84° (water) whose structure was analyzed by periodate oxidation and methylation techniques.

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Syothesis of 3-Deoxy-3-nitro-D-xylose

Canadian Journal of Chemistry ◽

10.1139/v71-539 ◽

1971 ◽

Vol 49 (19) ◽

pp. 3238-3239 ◽

Cited By ~ 2

Author(s):

Jan Kovář ◽

Hans H. Baer

Keyword(s):

Acid Hydrolysis ◽

Title Compound ◽

Periodate Oxidation ◽

Borohydride Reduction ◽

Hydrolysis Of

Crystalline 3-deoxy-3-nitro-α-D-xylose (5) was obtained in 40% over-all yield by periodate oxidation of 3-deoxy-1,2-O-isopropylidene-3-nitro-α-D-glucofuranose (2) followed by borohydride reduction and acid hydrolysis. In addition to the intermediate 3-deoxy-1,2-O-isopropylidene-3-nitro-α-D-xylofuranose (4), a small amount of an isomer probably having the D-ribo configuration was isolated. The title compound (5) was also obtained by hydrolysis of its methyl β-pyranoside (1).

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THE STRUCTURE OF THE EXTRACELLULAR POLYSACCHARIDE OF AZOTOBACTER INDICUM

Canadian Journal of Chemistry ◽

10.1139/v63-414 ◽

1963 ◽

Vol 41 (11) ◽

pp. 2826-2835 ◽

Cited By ~ 13

Author(s):

V. M. Parikh ◽

J. K. N. Jones

Keyword(s):

Glucuronic Acid ◽

Extracellular Polysaccharide ◽

Molar Ratio ◽

Linear Molecule ◽

Partial Hydrolysis ◽

Major Fraction ◽

Sodium Metaperiodate ◽

Unit Reduction ◽

Hydrolysis Of

The extracellular polysaccharide of the Azotobacter indicum has been shown to be a mixture of two polymers of which the acidic polymer was a major fraction. The acidic polymer contained D-glycero-D-mannoheptose in the molar ratio of 1:1:1 plus traces of mannose. It consumed 1 mole of sodium metaperiodate per mole of an average anhydroaldose unit and released 0.95 moles of formaldehyde per anhydroheptose unit. Reduction of the oxidized polymer followed by hydrolysis yielded D-glucose, glycerose, glycolaldehyde, and glycerol. Complete fission of the methylated polymer yielded 2,3-di-O-methyl-D-glucuronic acid, 2,4,6,-tri-O-methyl α-D-glucose and 3,4,6,7-tetra-O-methyl D-glycero-D-mannoheptose. Partial hydrolysis of the methylated polymer produced a methylated aldotriouronic acid composed of 1 mole each of 2,3-di-O-methyl-D-glucuronic acid, 2,4,6-tri-O-methyl-D-glucose and 3,4,6,7-tetra-O-methyl D-glycero-D-mannoheptose. A methylated aldobiouronic acid was also produced and was shown to be composed of 2,3-di-O-methyl-D-glucuronic acid and 2,4,6-tri-O-methyl D-glucose.On the basis of these results it is proposed that the polysaccharide is a linear molecule composed of repeating units of D-glucuronic acid, D-glucose, and D-glycero-D-mannoheptose.

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

Biochemical Journal ◽

10.1042/bj1330227 ◽

1973 ◽

Vol 133 (2) ◽

pp. 227-241 ◽

Cited By ~ 30

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.

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