Structure determination of galacto-oligosaccharides by pyridylamination and NMR spectroscopy

Kimura, Kazumasa; Matsumoto, Kunihiro; Ishihara, Chiyoko; Harada, Kouichi; Miyagi, Akihiko

doi:10.1016/0008-6215(94)00010-d

Cited by 28 publications

(27 citation statements)

References 13 publications

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“…However, MALDI-FTICR MS analysis of GOS syrup clearly demonstrated that there were oligosaccharides with DP of up to 15. This increase in resolution of the oligosaccharides with higher DP is likely due to the superior sensitivity and capabilities of FTICR MS compared with the highperformance liquid chromatography and nuclear magnetic resonance techniques used previously for GOS analysis (5,7,20). Similar results were reported for plant-derived fructooligosaccharides when they were analyzed by MALDI-FTICR MS (17).…”

Section: Discussionsupporting

confidence: 68%

“…It has been shown that GOS with DP of 2 and 3 can have different isomeric structures (5,7). Tandem MS analysis performed with oligosaccharides with DP of 3, 4, and 5 yielded cross-ring cleavage fragment ions that have been described for oligosaccharides containing ␤(1-6) linkages or ␤(1-3) linkages (22).…”

Section: Discussionmentioning

confidence: 99%

“…GOS structures are highly variable and dependent on the enzyme and conditions used during their synthesis (5,7,23). Previous work suggested that the upper limit for the DP for GOS is 8 (11).…”

Section: Discussionmentioning

confidence: 99%

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Glycoprofiling Bifidobacterial Consumption of Galacto-Oligosaccharides by Mass Spectrometry Reveals Strain-Specific, Preferential Consumption of Glycans

Barboza¹,

Sela

Pirim³

et al. 2009

Appl Environ Microbiol

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Galacto-oligosaccharides (GOS) are versatile food ingredients that possess prebiotic properties. However, at present there is a lack of precise analytical methods to demonstrate specific GOS consumption by bifidobacteria. To better understand the role of GOS as prebiotics, purified GOS (pGOS) without disaccharides and monosaccharides was prepared and used in bacterial fermentation experiments. Growth curves showed that all bifidobacteria assayed utilized and grew on pGOS preparations. We used a novel mass spectrometry approach involving matrix-assisted laser desorption ionization-Fourier transform ion cyclotron resonance (MALDI-FTICR) to determine the composition of oligosaccharides in GOS syrup preparations. MALDI-FTICR analysis of spent fermentation media demonstrated that there was preferential consumption of selected pGOS species by different bifidobacteria. The approach described here demonstrates that MALDI-FTICR is a rapid-throughput tool for comprehensive profiling of oligosaccharides in GOS mixtures. In addition, the selective consumption of certain GOS species by different bifidobacteria suggests a means for targeting prebiotics to enrich select bifidobacterial species.

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Section: Discussionsupporting

confidence: 68%

Section: Discussionmentioning

confidence: 99%

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Glycoprofiling Bifidobacterial Consumption of Galacto-Oligosaccharides by Mass Spectrometry Reveals Strain-Specific, Preferential Consumption of Glycans

Barboza¹,

Sela

Pirim³

et al. 2009

Appl Environ Microbiol

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“…Galactan oligosaccharides and maltodextrin standards were labeled with 2AP as described previously (Hase, 1994;Kimura et al, 1995). Excess 2AP was removed from the reaction by extraction with 1:1 phenol:chloroform (3 3 5 mL), followed by desalting on a Sephadex G-10 column in a buffer of 10 mM ammonium bicarbonate.…”

Section: Preparation Of 2ap-derivatized Oligosaccharidesmentioning

confidence: 99%

Exploring the Ultrastructural Localization and Biosynthesis of β(1,4)-Galactan in Pinus radiata Compression Wood

et al. 2009

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Softwood species such as pines react to gravitropic stimuli by producing compression wood, which unlike normal wood contains significant amounts of b(1,4)-galactan. Currently, little is known regarding the biosynthesis or physiological function of this polymer or the regulation of its deposition. The subcellular location of b(1,4)-galactan in developing tracheids was investigated in Pinus radiata D. Don using anti-b(1,4)-galactan antibodies to gain insight into its possible physiological role in compression wood. b(1,4)-Galactan was prominent and evenly distributed throughout the S2 layer of developing tracheid cell walls in P. radiata compression wood. In contrast, b(1,4)-galactan was not detected in normal wood. Greatly reduced antibody labeling was observed in fully lignified compression wood tracheids, implying that lignification results in masking of the epitope. To begin to understand the biosynthesis of galactan and its regulation, an assay was developed to monitor the enzyme that elongates the b(1,4)-galactan backbone in pine. A b(1,4)-galactosyltransferase (GalT) activity capable of extending 2-aminopyridine-labeled galacto-oligosaccharides was found to be associated with microsomes. Digestion of the enzymatic products using a b(1,4)-specific endogalactanase confirmed the production of b(1,4)-galactan by this enzyme. This GalT activity was substantially higher in compression wood relative to normal wood. Characterization of the identified pine GalT enzyme activity revealed pH and temperature optima of 7.0 and 20°C, respectively. The b(1,4)-galactan produced by the pine GalT had a higher degree of polymerization than most pectic galactans found in angiosperms. This observation is consistent with the high degree of polymerization of the naturally occurring b(1,4)-galactan in pine.

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“…B i o a c t i v e C a r b o h y d r a t e s a n d D i e t a r y F i b r e 5 ( 2 0 1 5 ) 1 3 7 -1 4 5 equipped with a 120-10 cartridge and lyophilized as described by Kimura, Matsumoto, Ishihara, Harada, and Miyagi (1995).…”

Section: Pyridylamination Of the β-Gluco-oligosaccharidesmentioning

confidence: 99%

An alternative strategy for structural glucanomics using β-gluco-oligosaccharides from the brown algae Ecklonia stolonifera as models

Sumiyoshi

Miyanishi

Nakakita

et al. 2015

Bioactive Carbohydrates and Dietary Fibre

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Structure determination of galacto-oligosaccharides by pyridylamination and NMR spectroscopy

Cited by 28 publications

References 13 publications

Glycoprofiling Bifidobacterial Consumption of Galacto-Oligosaccharides by Mass Spectrometry Reveals Strain-Specific, Preferential Consumption of Glycans

Glycoprofiling Bifidobacterial Consumption of Galacto-Oligosaccharides by Mass Spectrometry Reveals Strain-Specific, Preferential Consumption of Glycans

Exploring the Ultrastructural Localization and Biosynthesis of β(1,4)-Galactan in Pinus radiata Compression Wood

An alternative strategy for structural glucanomics using β-gluco-oligosaccharides from the brown algae Ecklonia stolonifera as models

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