The Constitution of a Methyl Glucuronoxylan From Kapok (Ceiba Pentandra)

Currie, A. L.; Timell, T. E.

doi:10.1139/v59-126

Cited by 13 publications

(4 citation statements)

References 20 publications

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“…EXPERIR/IENT.-IL General experi~nental conditions were the same as described previously (24). Solvents (v/v) used for separating sugars on the paper chromatograin were (A) ethyl acetateacetic acid -water (9:2:2), (B) butan-1-01 -pyridine -water (10:3:3), (C) butan-1-01 -ethanol -water (40: 11 : 19), and (D) butan-2-one -water (89: 11).…”

Section: Akd Disciissionmentioning

confidence: 99%

“…Extractive-free wood meal froin a sound, 25-year-old specinlen of sugar maple':' (500 g, 40-60 mesh) was exhaustively extracted by shaliing with 24% (\v/w) aqueous potassi~lill hydroxide (3.5 liters) as described previously (15,16,24). Tlle recovered product was dried fro111 petroleum ether i i z vaczlo to give 37 g (12.3%) of a 11-l~ite powder.…”

Section: Isolation Of the Heinicellz~losementioning

confidence: 99%

“…The molecular weights of the original hemicellulose and of its methyl derivative were carried out by oslnotic pressure ~neasurements as described elsewhere (24,34). T h e results obtained are presented in Table I.…”

Section: Determination Of Ilroleczilar Weightsmentioning

confidence: 99%

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The Constitution of a Hemicellulose From Sugar Maple (Acer Saccharum)

Timell¹

1959

Can. J. Chem.

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Partial hydrolysis of the main hemicellulose constituent of sugar maple (ilcer saccharntlz) has yielded D-xyloSe, D-galacturonic acid, 4-0-methyl-D-gl~rcuronic acid, and 2-0-(4-0-methyla-D-glucosyluronic acid)-D-xplose. Hydrolysis of the fully methylated polysaccharide gave a mixture of 2-0-and 3-O-methyl-D-xylose, 2,3-di-0-n1ethyl-~-xylose, 2,3,4-tri-O-methyl-~-xplose, and 2-0-(2,3,4-tri-0-n~etl~yl-a-~-gl~1cosyluronic acid)-3-0-methyl-D-sylose in a mole ratio of 3 : 111 : 1 : 12. The number-average degrees of polymerization of the native and the lnethylated polysaccharide were 205 and 149, respectively. These data indicate that the hemicellulose is composed of a linear chain of 1,4-linked P -D -x~~o s~ residues and that on the ax-erage every tenth residue of the chain carries a ternlinal 4-O-methyl-~-glucuronic acid residue attached through its C?. The structure of tile polysaccharide is similar to that of the main hernicellulose component of European beech, \\,bite birch, and yello\\-birch.Sugar maple is an inlportani hardwood species in the lort the astern part of this continent. Ritter and co-worlcers (1, 2) have st~idied the general conlposition of various he~nicellulose fractions from this wood and chromatographic evidence for the presence of 4-0-methyl glucuronic acid has been reported by Nelson and Schuerch (3). The structure of the same hemicellulose has been s t~~d i e d by Neubauer and Purves (4), who concluded that the polysaccharide ~7 a s composed of a branched baclcbone of 1,4-linked xylose residues, some of which carried terrniiial 0-methyl glucuro~~ic acid residues. I n a previous investigation (5) the molecular properties of a native cellulose from sugar maple were studied. The present paper is concerned with the constitution and properties of the main heniicellulose component of this species. RESULTS AKD DISCIiSSIONThe high pentosan content of the \vood (18.5%) indicated that the preponderant l~emicellulose \vas a xylan. When the mood was extracted wit11 alkali, a heinicellulose was obtained in a yield of 12.4%, giving D-x).~os~ and three uronic acid compounds on partial hydrolysis. The sugar acids were separated from the xylose oil ail anion exchange resin and the mixture obtained was resolved on a charcoal coluil~n to yield galacturonic acid, 4-0-illethyl gluc~~ronic acid, and an aldobiouronic acid. T h e hexuro~iic acids were identified cI~ron1atographical1~-whereas the structure of the aldobiouronic acid was proved by the following experiments.Reduction of the methyl glycoside methyl ester of the alclobiouro~iic acid followecl by l~ydrolysis gave D -X J~~O S~ and 4-0-methyl-D-glucose. When the neutral disaccharide was methylated to completion and hydrolyzed, :-1,4-di-0-rneth~~l-~-xylose and 2,3,4,6-tetra-0-niethyl-D-glucose were obtained. This evidence, together with the specific rotation of the compound (+100°) (G), sholvecl that the acid was 2-0-(~-O-1nethyl-or-~-~~1cosyluro1lic acid)-D-xylose.;\lIethanolysis of the fully methl.lated hemicell~ilose gave a inixture of glycosides...

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Section: Akd Disciissionmentioning

confidence: 99%

Section: Isolation Of the Heinicellz~losementioning

confidence: 99%

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The Constitution of a Hemicellulose From Sugar Maple (Acer Saccharum)

Timell¹

1959

Can. J. Chem.

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“…For MALDI analysis of GXM-catalyzed reaction products, non-radiolabeled S -adenosylmethionine (1 mM) was used. After 1-h incubation, the reaction mixture was passed through AG1-X4 anion exchange resin [34] . The bound MeGlcA-substituted xylooligomers were eluted with 3N acetic acid and the eluate was counted for the amount of radioactivity with a PerkinElmer scintillation counter (for radiolabeled S -adenosylmethionine) or subjected to MALDI analysis (for non-radiolabeled S -adenosylmethionine).…”

Section: Methodsmentioning

confidence: 99%

Identification and Biochemical Characterization of Four Wood-Associated Glucuronoxylan Methyltransferases in Populus

et al. 2014

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Wood is one of the promising bioenergy feedstocks for lignocellulosic biofuel production. Understanding how wood components are synthesized will help us design strategies for better utilization of wood for biofuel production. One of the major wood components is xylan, in which about 10% of xylosyl residues are substituted with glucuronic acid (GlcA) side chains. All the GlcA side chains of xylan in wood of Populus trichocarpa are methylated, which is different from Arabidopsis xylan in which about 60% of GlcA side chains are methylated. Genes responsible for methylation of GlcA side chains in Populus xylan have not been identified. Here, we report genetic and biochemical analyses of four DUF579 domain-containing proteins, PtrGXM1, PtrGXM2, PtrGXM3 and PtrGXM4, from Populus trichocarpa and their roles in GlcA methylation in xylan. The PtrGXM genes were found to be highly expressed in wood-forming cells and their encoded proteins were shown to be localized in the Golgi. When overexpressed in the Arabidopsis gxm1/2/3 triple mutant, PtrGXMs were able to partially complement the mutant phenotypes including defects in glucuronoxylan methyltransferase activity and GlcA methylation in xylan, indicating that PtrGXMs most likely function as glucuronoxylan methyltransferases. Direct evidence was provided by enzymatic analysis of recombinant PtrGXM proteins showing that they possessed a methyltransferase activity capable of transferring the methyl group onto GlcA-substituted xylooligomers. Kinetic analysis showed that PtrGXMs exhibited differential affinities toward the GlcA-substituted xylooligomer acceptor with PtrGXM3 and PtrGXM4 having 10 times higher K m values than PtrGXM1 and PtrGXM2. Together, these findings indicate that PtrGXMs are methyltransferases mediating GlcA methylation in Populus xylan during wood formation.

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The optical rotation of wood xylans

Gutmann

Timell

1965

J. polym. sci., C Polym. symp.

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Previously derived equations relating the specific rotation and chemical composition of 4‐O‐methylghicurono‐xylans and arabino‐4‐O‐methylglucurono‐xylans have been found to be partly incorrect because of the assignment of an erroneous value to the rotatory contribution of the 4‐O‐methyl‐α‐D‐glucuronosyl xylose residue. The correct value was calculated from the known molar rotations of xylobiose and 22‐(4‐O‐methyl‐α‐D‐glucuronosyl) xylotriose. Approximately the same values were obtained from the specific rotations of five carefully purified 4‐O‐methylglucurono‐xylans, containing different proportions of acid side chains, and from the rotations of an aldopentaouronic and an aldohexaouronic acid. A revised equation was used for estimating the specific rotation of several arabino‐4‐O‐methylglucunmo‐xylans from various softwoods. Contrary to the earlier results, a satisfactory agreement was found to exist in most cases between found and calculated values.

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The Constitution of a Methyl Glucuronoxylan From Kapok (Ceiba Pentandra)

Cited by 13 publications

References 20 publications

The Constitution of a Hemicellulose From Sugar Maple (Acer Saccharum)

The Constitution of a Hemicellulose From Sugar Maple (Acer Saccharum)

Identification and Biochemical Characterization of Four Wood-Associated Glucuronoxylan Methyltransferases in Populus

The optical rotation of wood xylans

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