Carbohydrate structural analysis of wheat flour arabinogalactan protein

Tryfona, Theodora; Liang, Hui-Chung; Kotake, Toshihisa; Kaneko, Satoshi; Marsh, Justin; Ichinose, Hitomi; Lovegrove, Alison; Tsumuraya, Yoichi; Shewry, Peter R.; Stephens, Elaine; Dupree, Paul

doi:10.1016/j.carres.2010.09.018

Cited by 105 publications

(97 citation statements)

References 45 publications

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“…Involvement of β-(1→6)-galactooligosaccharide side chains of various lengths modified with L-Ara residues in radish root AGP is essentially consistent with the structure we have proposed for wheat flour and Arabidopsis leaf AGPs, 20,21) in which relatively short β-(1→3)-galactans serve as the main chains. Actually, wheat flour AG contains various L-Araf-containing galactooligosaccharides as well as L-Arap-containing saccharides such as β-Gal-(1→6) [β-L-Arap-(1→3)]-β-Gal-(1→6)-β-Gal-(1→6)-Gal (similar to N5-2, but with β-L-Arap groups).…”

Section: Discussionsupporting

confidence: 88%

“…8) Basically, the same structural feature was reported for AGs isolated from wheat flour and Arabidopsis leaves. 20,21) For the present study, we have isolated Larabino-galactooligosaccharides from the same radish root AGP and analyzed their structures, in particular the localization of L-Araf units along β-(1→6)-galactan side chains. Almost nothing is known about the physiological functions of L-Ara units in AG so far.…”

Section: )mentioning

confidence: 99%

“…Sugars were derivatized with the fluorophore 8-aminonaphthalene-1,3,6-trisulphonic acid (ANTS), subjected to gel electrophoresis, and recorded as described previously. 20) Gas liquid chromatography (GLC) of neutral sugars as their alditol acetate derivatives was done with a Shimadzu gas chromatograph GC-6A fitted with a column (0.28 mm × 50 m) of Silar-10C, according to the method of Albersheim et al 28) Methylation was performed by the Hakomori method, 29) and the products were analyzed by GLC. The carboxyl groups of 4-MeGlcA residues in permethylated acidic oligomers were reduced with LiAlH4 in tetrahydrofuran for 1 h at 50°C, 30) and the resulting methylated derivatives of 4-O-methyl-Glc were analyzed by GLC.…”

Section: Carbohydrate Analysesmentioning

confidence: 99%

“…Samples were analyzed by MALDI-TOF/TOF-MS/MS (4700 proteomics analyzer, Applied Biosystems, Foster City, CA, USA) as previously described. 20) Permethylated samples dissolved in MeOH (5 μL) were mixed with 5 μL of 2,5-dihydroxybenzoic acid (2,5-DHB) matrix (10 mg/mL dissolved in 50% MeOH) and 1 μL of the mixture was spotted on a MALDI target plate and was rapidly dried in a vacuum desiccator in order to produce small crystals for easy spectral acquisition. High energy MALDI-collision induced dissociation (MALDI-CID) spectra were acquired with an average of 10,000 laser shots/spectrum, using high collision energy (1 kV).…”

Section: Permethylation Of Ag Oligosaccharides and Maldi-tof/tof/-ms/msmentioning

confidence: 99%

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Enzymatic fragmentation of carbohydrate moieties of radish arabinogalactan-protein and elucidation of the structures

Shimoda

Okabe

Kotake

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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We investigated the structures of L-arabino-galactooligosaccharides released from the sugar moieties of a radish arabinogalactan-protein (AGP) by the action of exo-β-(1→3)-galactanase. We detected a series of neutral β-(1→6)-linked galactooligosaccharides forming branches of one to up to at least 19 consecutive Gal groups, together with corresponding acidic derivatives terminating in 4-O-methyl-glucuronic acid (4-Me-GlcA) at the non-reducing end. Some oligosaccharide chains of degree of polymerization (dp) higher than 3 for neutral, and 4 for acidic oligomers were modified with L-Araf residues. The acidic tetrasaccharide 4-Me-β-GlcA-(1→6)[α-L-Araf-(1→3)]-β-Gal-(1→6)-Gal was detected as an abundant L-Araf-containing oligosaccharide among these neutral and acidic oligomers. A pentasaccharide containing an additional L-Araf group attached to the L-Ara in the tetrasaccharide through an α-(1→5)-linkage was also found. We observed L-arabino-galactooligosaccharides substituted with single or disaccharide L-Araf units at different Gal residues along these neutral and acidic β-(1→6)-galactooligosaccharide chains, indicating that these side chains are highly variable in length and substituted variously with L-Araf residues.

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Section: Discussionsupporting

confidence: 88%

Section: )mentioning

confidence: 99%

Section: Carbohydrate Analysesmentioning

confidence: 99%

Section: Permethylation Of Ag Oligosaccharides and Maldi-tof/tof/-ms/msmentioning

confidence: 99%

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Enzymatic fragmentation of carbohydrate moieties of radish arabinogalactan-protein and elucidation of the structures

Shimoda

Okabe

Kotake

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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“…The GT31 family encodes inverting GT enzymes including GALT1, which encodes an N-glycan b-1/3 galactosyltransferase in Arabidopsis (Strasser et al, 2007). The nature of AGP glycosylation has recently been characterized in detail in wheat cv Cadenza and shown to contain numerous Galp b-1/6 and Galp b-1/3 linkages requiring inverting activity (Tryfona et al, 2010). Therefore, it is possible that different but related GT31 genes could be responsible for the transfer of Gal to AGP.…”

Section: Irx8mentioning

confidence: 99%

Cell Walls of Developing Wheat Starchy Endosperm: Comparison of Composition and RNA-Seq Transcriptome

et al. 2011

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The transcriptome of the developing starchy endosperm of hexaploid wheat (Triticum aestivum) was determined using RNASeq isolated at five stages during grain fill. This resource represents an excellent way to identify candidate genes responsible for the starchy endosperm cell wall, which is dominated by arabinoxylan (AX), accounting for 70% of the cell wall polysaccharides, with 20% (1,3;1,4)-b-D-glucan, 7% glucomannan, and 4% cellulose. A complete inventory of transcripts of 124 glycosyltransferase (GT) and 72 glycosylhydrolase (GH) genes associated with cell walls is presented. The most highly expressed GT transcript (excluding those known to be involved in starch synthesis) was a GT47 family transcript similar to Arabidopsis (Arabidopsis thaliana) IRX10 involved in xylan extension, and the second most abundant was a GT61. Profiles for GT43 IRX9 and IRX14 putative orthologs were consistent with roles in AX synthesis. Low abundances were found for transcripts from genes in the acyl-coA transferase BAHD family, for which a role in AX feruloylation has been postulated. The relative expression of these was much greater in whole grain compared with starchy endosperm, correlating with the levels of bound ferulate. Transcripts associated with callose (GSL), cellulose (CESA), pectin (GAUT), and glucomannan (CSLA) synthesis were also abundant in starchy endosperm, while the corresponding cell wall polysaccharides were confirmed as low abundance (glucomannan and callose) or undetectable (pectin) in these samples. Abundant transcripts from GH families associated with the hydrolysis of these polysaccharides were also present, suggesting that they may be rapidly turned over. Abundant transcripts in the GT31 family may be responsible for the addition of Gal residues to arabinogalactan peptide.

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Production and Bioactivity of Oligosaccharides from Biomass Hemicelluloses

Gullón

González‐Munñoz

et al. 2014

Food Oligosaccharides

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Carbohydrate structural analysis of wheat flour arabinogalactan protein

Cited by 105 publications

References 45 publications

Enzymatic fragmentation of carbohydrate moieties of radish arabinogalactan-protein and elucidation of the structures

Enzymatic fragmentation of carbohydrate moieties of radish arabinogalactan-protein and elucidation of the structures

Cell Walls of Developing Wheat Starchy Endosperm: Comparison of Composition and RNA-Seq Transcriptome

Production and Bioactivity of Oligosaccharides from Biomass Hemicelluloses

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