CONSTITUTION OF AN ARABOGALACTAN FROM JACK PINE (PINUS BANKSIANA LAMB)

1957 ◽  
Vol 35 (9) ◽  
pp. 1010-1019 ◽  
Author(s):  
C. T. Bishop
Keyword(s):  
Methyl Ether ◽  
Pinus Banksiana ◽  
Jack Pine ◽  
Degree Of Polymerization ◽  
Average Degree ◽  
Water Soluble ◽  
Molar Ratio ◽  
Hydrolysis Of ◽  
Homogeneous Hydrolysis

A water soluble arabogalactan isolated from jack pine was shown to have a molar ratio of arabinose to galactose of 1:13, and a number average degree of polymerization of 53 ± 3. Fractionation data and electrophoresis indicated that the arabogalactan was homogeneous. Hydrolysis of the methyl ether of the polysaccharide yielded 2,3,5-tri-O-methyl-L-arabinose (4 moles); 2,3,4,6-tetra-O-methyl-D-galactose (12–13 moles); 2,3,4-tri-O-methyl-D-galactose (19 moles); 2,6-di-O-methyl-D-galactose (1 mole); and 2,4-di-O-methyl-D-galactose (14 moles). Some features of the structure of the arabogalactan are discussed on the basis of these results.

THE WATER-SOLUBLE POLYSACCHARIDES OF DERMATOPHYTES: II. A GLUCAN FROM MICROSPORUM QUINCKEANUM

1963 ◽  
Vol 41 (10) ◽  
pp. 2621-2627 ◽  
Author(s):  
H. Alfes ◽  
C. T. Bishop ◽  
F. Blank
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Candida Albicans ◽  
Minimum Degree ◽  
Relative Number ◽  
Degree Of Polymerization ◽  
Water Soluble ◽  
Molar Ratio ◽  
Branch Points ◽  
Degree Of Branching ◽  
Hydrolysis Of

A levorotatory glucan with a minimum degree of polymerization of 36 has been isolated from the water-soluble polysaccharides of the dermatophyte Microsporum quinckeanum. Hydrolysis of the methylated glucan yielded the following O-methyl-D-glucoses: 2,3,4,6-tetra-(10.2 mole%); 2,3,4-tri- (57.7 mole%); 2,4,6-tri- (22.2 mole%); 2,4-di- (8.2 mole%); and 2-mono- (1.6 mole%). The glucan consumed 1.53 moles of periodate with production of 0.70 mole of formic acid per mole anhydroglucose. Reduction and hydrolysis of the periodate-oxidized glucan yielded glycerol, erythritol, and D-glucose in a molar ratio of 72.3:0.6:27.1. The results showed that the glucan consisted of β-D-glucopyranose units joined in straight chains by 1 → 6 (57%) and 1 → 3 (24%) linkages. Approximately 3 in every 37 glucose residues constitute branch points in the glucan with branches occurring at the C6 and C3 positions of the same glucose unit. The glucan bears some resemblance to the yeast glucans of Saccharomyces cerevisiae and Candida albicans but differs from them in the relative number of 1 → 6 and 1 → 3 linkages and in the degree of branching.

CONSTITUTION OF A GLUCOMANNAN FROM JACK PINE (PINUS BANKSIANA, LAMB)

1960 ◽  
Vol 38 (6) ◽  
pp. 793-804 ◽  
Author(s):  
C. T. Bishop ◽  
F. P. Cooper
Keyword(s):  
Pinus Banksiana ◽  
Group Analysis ◽  
Periodate Oxidation ◽  
Jack Pine ◽  
Degree Of Polymerization ◽  
Molar Ratio ◽  
Partition Chromatography ◽  
Pine Wood ◽  
Terminal Units ◽  
End Group

A hemicellulose fraction from jack pine wood has been shown to contain D-mannose, D-glucose, and D-galactose in a molar ratio of 49:17:2. The glucomannan was electrophoretically homogeneous and showed a degree of polymerization of 18–21 by three different methods of end group analysis. Methylation and hydrolysis yielded the following O-methyl ethers: 2,3,4,6-tetra-O-methyl-D-glucose (2.8 moles); 2,3,4,6-tetra-O-methyl-D-galactose (1 mole); 2,3,6-tri-O-methyl-D-mannose (52 moles); 2,3,6-tri-O-methyl-D-glucose (15.3 moles); di-O-methyl-D-glucose (1 mole); di-O-methyl-D-galactose (2 moles). Lack of survival of any monosaccharides in the periodate-oxidized glucomannan showed that there was no branching through C2 or C3 of any of the units. Gas–liquid partition chromatography was used to analyze products from methylation and hydrolysis and from periodate oxidation and reduction of the polysaccharides. The results showed that the glucomannan from jack pine was composed of 1 → 4 linked β-D-mannose and β-D-glucose residues with D-galactose residues present as non-reducing terminal units. Branching, if any, must occur through C6 of units making up the polysaccharide. This structure is compared with those of glucomannans found in other soft woods.

ENZYMIC HYDROLYSIS OF A GLUCOMANNAN FROM JACK PINE (PINUS BANKSIANA LAMB.)

1961 ◽  
Vol 39 (4) ◽  
pp. 815-826 ◽  
Author(s):  
O. Perila ◽  
C. T. Bishop
Keyword(s):  
Pinus Banksiana ◽  
Jack Pine ◽  
Molar Ratio ◽  
Enzymic Hydrolysis ◽  
Hydrolysis Of

A crude glucomannan was isolated from jack pine holocellulose in 17% yield. Repeated delignification and copper complexing of this product provided a purified glucomannan (5% of the holocellulose) containing glucose, mannose, galactose, and xylose in a molar ratio of 10:25:1:1. This polysaccharide was hydrolyzed by a commercial hemicellulase preparation, the cleavage products being removed by continuous dialysis of the reaction mixture. The following oligosaccharides were isolated from the hydrolyzate and identified; yields are based on the glucomannan:[Formula: see text]

THE HEMICELLULOSE OF WHITE ELM (ULMUS AMERICANA) II. CONSTITUTION OF THE METHYL GLUCURONO-XYLAN

1958 ◽  
Vol 36 (11) ◽  
pp. 1467-1474 ◽  
Author(s):  
J. K. Gillham ◽  
T. E. Timell
Keyword(s):  
Glucuronic Acid ◽  
Degree Of Polymerization ◽  
Average Degree ◽  
Glycosidic Bond ◽  
Molar Ratio ◽  
Side Chain ◽  
Partial Hydrolysis ◽  
Ulmus Americana ◽  
Hydrolysis Of

The wood of white elm (Ulmusamericana) has been found to contain less xylan than most other hardwoods. Partial hydrolysis of the hemicellulose component yielded an aldotriouronic acid, a glucuronosyl xylose, 2-O-(4-O-methyl-α-D-glucopyranosyluronic acid)-D-xylopyranose, 4-O-methyl-D-glucuronic acid, and galacturonic acid.Hydrolysis of the fully methylated polysaccharide gave a mixture of 2-O- and 3-O-methyl-D-xylose, 2,3-di-O-methyl-D-xylose, 2,3,4-tri-O-methyl-D-xylose, and 2-O-(2,3,4-tri-O-methyl-α-D-glucopyranosyluronic acid)-3-O-methyl-D-xylopyranose in a molar ratio of 6:124:1:14. The number-average degree of polymerization of the methylated hemicellulose was 133 and that of the native polymer 185. On the basis of this and other evidence it is suggested that the xylan is linear and contains 185 1,4-linked β-D-xylopyranose residues, every seventh of which carries a single terminal side chain of 4-O-methyl-D-glucuronic acid attached by an α-glycosidic bond through C2 of the xylose. The number of acid groups is larger than in other hardwood hemicelluloses so far studied.

STRUCTURE OF A GALACTURONAN FROM SUNFLOWER PECTIC ACID

1966 ◽  
Vol 44 (11) ◽  
pp. 1275-1282 ◽  
Author(s):  
V. Zitko ◽  
C. T. Bishop
Keyword(s):  
Galacturonic Acid ◽  
Periodate Oxidation ◽  
Degree Of Polymerization ◽  
Critical Assessment ◽  
Molar Ratio ◽  
Aqueous Methanol ◽  
Pectic Acid ◽  
Potassium Borohydride ◽  
Rate Of Hydrolysis ◽  
Hydrolysis Of

Fractions of sunflower pectic acid containing 89.8%, 94.2%, and 91.4% of D-galacturonic acid were carboxyl reduced as their methyl or ethylene glycol esters by potassium borohydride. Critical assessment of the effects of three different solvents (water, 80% aqueous dimethyl sulfoxide, and 80% aqueous methanol) on the efficiency of reduction showed that the latter solvent was best. The reductions caused a decrease in the degree of polymerization from 270 to 21. Measurement of the rates of hydrolysis of partially reduced pectic acids containing 90%, 41.6%, 19.9%, 11.0%, and 0.65% of D-galacturonic acid showed that the rate of hydrolysis was directly related to the proportion of galacturonosidic linkages present. Methylation and hydrolysis of the carboxyl-reduced pectic acid fractions yielded 2,3,4,6-tetra-O-methyl-D-galactose and 2,3,6-tri-O-methyl-D-galactose in an approximate molar ratio of 1:20. Results of the periodate oxidation of the carboxyl-reduced pectic acid supported the conclusion inferred from the methylation results that the pectic acid was a linear polymer of 1 → 4 linked α-D-galacturonic acid units.

CONSTITUTION OF A WATER SOLUBLE HEMICELLULOSE FROM AMERICAN BEECHWOOD (FAGUS GRANDIFOLIA)

1957 ◽  
Vol 35 (6) ◽  
pp. 556-564 ◽  
Author(s):  
G. A. Adams
Keyword(s):  
Average Molecular Weight ◽  
Periodate Oxidation ◽  
Reducing Power ◽  
Fagus Grandifolia ◽  
Water Soluble ◽  
Hot Water ◽  
Molar Ratio ◽  
Weight Average Molecular Weight ◽  
Homogeneous Fraction ◽  
Hydrolysis Of

Extraction of beechwood chlorite holocellulose with hot water yielded a hemicellulose in 13.4% yield (based on original extractive-free wood) containing D-xylose 72%, D-galactose 11.0%, and uronic acid 13.2%. Purification of the crude hemicellulose by complexing with Fehling's solution yielded a chemically homogeneous fraction containing D-xylose 83% and 4-O-methyl-D-glucuronic acid 15.5%. Hydrolysis of the fully methylated hemicellulose yielded 2,3,4-tri-O-methyl-D-xylose, 2,3-di-O-methyl-D-xylose, 3-O-methyl-D-xylose, and 3-O-methyl-2-O-(2,3,4-tri-O-methyl-D-glucopyranosyluronic acid)-D-xylose in a molar ratio of 2:35:3:5. On the basis of the methylation data, periodate oxidation, reducing power determinations, and weight average molecular weight values a possible structure for the hemicellulose is proposed.

STRUCTURE OF AN ARABOGALACTAN FROM TAMARACK (LARIX LARICINA)

1960 ◽  
Vol 38 (2) ◽  
pp. 280-293 ◽  
Author(s):  
G. A. Adams
Keyword(s):  
Aqueous Solution ◽  
Water Soluble ◽  
Molar Ratio ◽  
Larix Laricina ◽  
Soluble Polysaccharide ◽  
Main Component ◽  
Hydrolysis Of

A water-soluble polysaccharide containing L-arabinose and D-galactose in a molar ratio 1:3.8 was isolated from tamarack. Fractionation with ethanol from aqueous solution yielded one main component which was judged to be homogeneous on the basis of electrophoresis and sedimentation data. Hydrolysis of the fully methylated polysaccharide yielded, 2,3,5-tri-O-methyl-L-arabinose (2 moles); 2,3,4,6-tetra-O-methyl-D-galactose (16 moles); 2,5-di-O-methyl-L-arabinose (5 moles); 2,3,4-tri-O-methyl-L-arabinose (5.5 moles); 2,3,4-tri-O-methyl-D-galactose (11 moles); 2,4,6-tri-O-methyl-D-galactose (3 moles); 2,6-di-O-methyl-D-galactose (1 mole); 2,4-di-O-methyl-D-galactose (20 moles); 2-O-methyl-D-galactose (3 moles).Possible structures for the arabogalactan are proposed and discussed on the basis of these results.

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.

CONSTITUTION OF A 4-O-METHYLGLUCURONOXYLAN FROM THE WOOD OF TREMBLING ASPEN (POPULUS TREMULOIDES MICHX.)

1961 ◽  
Vol 39 (5) ◽  
pp. 1059-1066 ◽  
Author(s):  
J. K. N. Jones ◽  
C. B. Purves ◽  
T. E. Timell
Keyword(s):  
Populus Tremuloides ◽  
Galacturonic Acid ◽  
Glucuronic Acid ◽  
Degree Of Polymerization ◽  
Average Degree ◽  
Quantitative Yield ◽  
Partial Hydrolysis ◽  
Trembling Aspen ◽  
Linear Framework ◽  
Hydrolysis Of

A 4-O-methylglucuronoxylan has been isolated in almost quantitative yield from the wood of trembling aspen (Populustretmuloides Michx.) The hemicellulose was electrophoretically homogeneous and had a number-average degree of polymerization of 212. Partial hydrolysis gave D-xylose, galacturonic acid, 4-O-methylglucuronic acid, and 2-O-(4-O-methyl-α-D-glucopyranosyluronic acid)-D-xylopyranose. Methanolysis and hydrolysis of the fully methylated polysaccharide, which contained 108 xylose residues per average molecule, gave 2-O-methylxylose, 2,3-di-O-methyl-D-xylose, 2,3,4-tri-O-methyl-D-xylose, and methyl 2-O-(2,3,4-tri-O-methyl-α-D-glucopyranosyluronic acid) -3-O-methyl-D-xylopyranoside in a mole ratio of 0.2:95:1:11. It is concluded that the hemicellulose contained a linear framework of approximately 200 (1 → 4)-linked β-D-xylopyranose residues and that, on the average, every ninth xylose unit carried a (1 → 2)-linked 4-O-methyl-α-D-glucuronic acid residue directly attached to the xylan backbone. The polysaccharide is evidently similar to the 4-O-methylglucuron-oxylans occurring in the wood of all arborescent angiosperms so far investigated.

CONSTITUTION OF THE HEMICELLULOSE FROM MESTA FIBER (HIBISCUS CANNABINUS)

1963 ◽  
Vol 41 (9) ◽  
pp. 2346-2350 ◽  
Author(s):  
S. K. Sen
Keyword(s):  
Molecular Weight ◽  
Uronic Acid ◽  
Average Molecular Weight ◽  
Analytical Data ◽  
Degree Of Polymerization ◽  
Hibiscus Cannabinus ◽  
Molar Ratio ◽  
Alkaline Solutions ◽  
Number Average Molecular Weight ◽  
Hydrolysis Of

The chlorite holocellulose of mesta fiber (Hibiscus cannabinus) was extracted with alkaline solutions of successively increasing concentration and finally with alkaline borate solution. Hemicellulose fractions (I–IV) were thus obtained. Analytical data are recorded for each fraction.Partial acid hydrolysis of the mesta hemicellulose gave 2-O-(4-O-methyl-α-D-glucopyranosyl uronic acid)-D-xylopyranose. Methanolysis and hydrolysis of the fully methylated hemicellulose (fraction II) gave a mixture of 3-O-methyl-D-xylose, 2,3-di-O-methyl-D-xylose, 2,3,4-tri-O-methyl-D-xylose, and 2-O-(2,3,4-tri-O-methyl-α-D-glucopyranosyl uronic acid)-3-O-methyl-D-xylopyranose in the approximate molar ratio of 1.6:34:1:6.4. The number-average molecular weight of the methylated polysaccharide was 18,400 ± 500 (degree of polymerization, 110 ± 3). The number-average molecular weight of the original hemicellulose (fraction II) was found to be 23,000 ± 500 (degree of polymerization, 164 ± 3). On the basis of this and other evidences it is suggested that the polysaccharide is composed of chains of 144 (1 → 4)-linked β-D-xylopyranose residues having approximately every seventh residue carrying a terminal 4-O-methyl-α-D-glucuronic acid residue linked through position 2. A small degree of branching in the backbone of D-xylose is indicated.

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