Characterization of O-acetyl-(4-O-methylglucurono)xylan isolated from birch and beech

Teleman, Anita; Tenkanen, Maija; Jacobs, Anna; Dahlman, Olof

doi:10.1016/s0008-6215(01)00327-5

Cited by 230 publications

(172 citation statements)

References 15 publications

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“…two-dimensional 1 h- 13 C hSQC nmr spectrum of acetylated xylan from wildtype Arabidopsis stems. acetylated xylan was extracted with DmSo 28 and digested with β-endoxylanase m6 (megazyme) to generate xylooligosaccharides, 16 which were subsequently subject to structural analysis using nmr spectroscopy. 29 the spectrum aligned at the top of the figure is the 1D 1 h nmr spectra of Arabidopsis xylan.…”

Section: 23mentioning

confidence: 99%

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Zhong

Teng

Lee

et al. 2014

Plant Signaling & Behavior

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Section: 23mentioning

confidence: 99%

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Zhong

Teng

Lee

et al. 2014

Plant Signaling & Behavior

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“…However, no tandem mass spectrometry studies were performed on the XOS ions produced by MALDI. ESI-MS was recently applied for the identification of underivatized olive pulp XOS, obtained by partial acid hydrolysis, both in positive [13,14] and negative [14] modes, allowing the identification of neutral oligosaccharides of xylose (Xyl) Xyl [3][4][5][6][7][8][9] , and acidic xylo-oligosaccharides substituted with MeGlcA (Xyl 2-11 MeGlcA) or GlcA (Xyl 3-5 GlcA) [13,14]. Tandem mass spectrometry analyses were performed on the observed ions allowing to confirm the presence of the acidic residue (MeGlcA and GlcA) and to propose a possible location along the XOS chain.…”

mentioning

confidence: 99%

Structural differentiation of uronosyl substitution patterns in acidic heteroxylans by electrospray tandem mass spectrometry

Reis

Pinto

Coimbra

et al. 2004

J. Am. Soc. Mass Spectrom.

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The structures of two oligomers of acidic xylo-oligosaccharides (XOS) of the same molecular weight (634 Da), Xyl 2 MeGlcAHex and Xyl 2 GlcA 2 were differentiated by electrospray tandem mass spectrometry (ESI-MS/MS). These oligomers were present in a mixture of XOS obtained by acid hydrolysis of heteroxylans extracted from Eucalyptus globulus wood (Xyl 2 MeGlcAHex) and Olea europaea olive fruit (Xyl 2 GlcA 2 ). In the ESI-MS spectra of the XOS, ions at m/z 657 and 652 were observed and assigned to [M ϩ Na] ϩ and [M ϩ NH 4 ] ϩ , respectively. The ESI-MS/MS spectrum of [M ϩ Na] ϩ ion of Xyl 2 MeGlcAHex showed the loss of Hex residue from the reducing end followed by the loss of MeGlcA moiety. Simultaneously, the loss of a Xyl residue from either the reducing or the non-reducing ends was detected. On the other hand, the fragmentation of Xyl 2 GlcA 2 occurs mainly by the loss of one and two GlcA residues or by the loss of the GlcAXyl moiety, due to the glycosidic bond cleavage between the two Xyl residues. Loss of one and two CO 2 molecules was only observed for this oligomer, where the GlcA are [1][2][3]. It is certain that the physicochemical properties of cell walls are strongly affected by GX structural features (nature and frequency of the branching side chains, degree of the acetylation, molecular weight, etc.), which knowledge is crucial with regard to the digestibility and processability behavior of plant/ fruit/vegetable tissues [1][2][3].Commonly GX structures, as other hemicelluloses, are elucidated by the coupling of wet chemistry with NMR techniques [4,5]. However, these methods have several limitations, such as insufficiently high sensitivity towards important structural features of minor abundance (lower 2 mol %) and the poor information revealed on the primary structure of heteroxylans. Mass spectrometry (MS), particularly tandem mass spectrometry using either matrix assisted laser desorption ionization (MALDI) or electrospray (ESI), was shown to be useful for oligosaccharides structural characterization [6 -8]. MS has been applied to the study of XOS, mainly using MALDI [9 -12]. However, no tandem mass spectrometry studies were performed on the XOS ions produced by MALDI. ESI-MS was recently applied for the identification of underivatized olive pulp XOS, obtained by partial acid hydrolysis, both in positive [13,14] and negative [14] modes, allowing the identification of neutral oligosaccharides of xylose (Xyl) Xyl 3-9 , and acidic xylo-oligosaccharides substituted with MeGlcA

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“…In addition to xylo-oligosaccharides with an O-acetyl group on X2, a xylo-tetraose having an O-acetyl ester on the nonreducing end xylosyl was observed following incubation with AxeA1. We cannot rule out the possibility that this O-acetyl is present on the O-4 position of the nonreducing end xylosyl residue and not on the O-2 or O-3 position typical of xylan (39,51). The O-4 position could be the result of internal migration, as has been proposed previously (27).…”

Section: Discussionmentioning

confidence: 76%

Biochemical Characterization and Relative Expression Levels of Multiple Carbohydrate Esterases of the Xylanolytic Rumen Bacterium Prevotella ruminicola 23 Grown on an Ester-Enriched Substrate

Kabel

Yeoman

Han

et al. 2011

Appl Environ Microbiol

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We measured expression and used biochemical characterization of multiple carbohydrate esterases by the xylanolytic rumen bacterium Prevotella ruminicola 23 grown on an ester-enriched substrate to gain insight into the carbohydrate esterase activities of this hemicellulolytic rumen bacterium. The P. ruminicola 23 genome contains 16 genes predicted to encode carbohydrate esterase activity, and based on microarray data, four of these were upregulated >2-fold at the transcriptional level during growth on an ester-enriched oligosaccharide (XOS FA,Ac ) from corn relative to a nonesterified fraction of corn oligosaccharides (AXOS). Four of the 16 esterases (Xyn10D-Fae1A, Axe1-6A, AxeA1, and Axe7A), including the two most highly induced esterases (Xyn10D-Fae1A and Axe1-6A), were heterologously expressed in Escherichia coli, purified, and biochemically characterized. All four enzymes showed the highest activity at physiologically relevant pH (6 to 7) and temperature (30 to 40°C) ranges. The P. ruminicola 23 Xyn10D-Fae1A (a carbohydrate esterase [CE] family 1 enzyme) released ferulic acid from methylferulate, wheat bran, corn fiber, and XOS FA,Ac , a corn fiber-derived substrate enriched in O-acetyl and ferulic acid esters, but exhibited negligible activity on sugar acetates. As expected, the P. ruminicola Axe1-6A enzyme, which was predicted to possess two distinct esterase family domains (CE1 and CE6), released ferulic acid from the same substrates as Xyn10D-Fae1 and was also able to cleave O-acetyl ester bonds from various acetylated oligosaccharides (AcXOS). The P. ruminicola 23 AxeA1, which is not assigned to a CE family, and Axe7A (CE7) were found to be acetyl esterases that had activity toward a broad range of mostly nonpolymeric acetylated substrates along with AcXOS. All enzymes were inhibited by the proximal location of other side groups like 4-O-methylglucuronic acid, ferulic acid, or acetyl groups. The unique diversity of carbohydrate esterases in P. ruminicola 23 likely gives it the ability to hydrolyze substituents on the xylan backbone and enhances its capacity to efficiently degrade hemicellulose.Hemicelluloses comprise a heterogeneous, highly branched mixture of complex polysaccharides. In plant cell walls, these polysaccharides form intimate associations with cellulose, pectin, and lignin and markedly reduce the degradability of plant fiber (20). In a microbial ecosystem such as the rumen, fiberdegrading microorganisms meet this challenge by operating as a consortium. Several hemicellulolytic rumen species, especially the ones belonging to Prevotella and Butyrivibrio, have been shown to synergistically enhance the rate and extent of plant cell wall hydrolysis during co-or sequential culturing with cellulolytic bacteria (12,18,31,32).The hemicelluloses present in the cell walls of grasses, cereals, and hardwoods largely comprise xylan, a polymer consisting of linear chains of D-xylopyranosyl residues linked through ␤-(134) glycosidic linkages. For grasses and cereals, the xylan backbone is heavily substitu...

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Characterization of O-acetyl-(4-O-methylglucurono)xylan isolated from birch and beech

Cited by 230 publications

References 15 publications

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Structural differentiation of uronosyl substitution patterns in acidic heteroxylans by electrospray tandem mass spectrometry

Biochemical Characterization and Relative Expression Levels of Multiple Carbohydrate Esterases of the Xylanolytic Rumen Bacterium Prevotella ruminicola 23 Grown on an Ester-Enriched Substrate

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