Evaluation of Interactions between Monosaccharides and a Stationary Phase Modified with Alkylboronic Acid by Means of a Liquid-Chromatographic Method

Soh, Nobuaki; Kitano, Koutaro; Imato, Toshihiko

doi:10.2116/analsci.18.1159

Cited by 7 publications

(6 citation statements)

References 8 publications

(9 reference statements)

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“…The observed order is also in good agreement with the elution order reported in our previous study [9], in which a separation behavior on an alkylboronic acid-modified support was examined by a liquid chromatographic method. Another interesting phenomenon is the response peak shape of the present SPR sensor among the saccharides, as shown in Figure 6.…”

Section: Responses Of Spr Sensor With the Sensor Chipsupporting

confidence: 91%

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Modification of a Thin Gold Film with Boronic Acid Membrane and Its Application to a Saccharide Sensor Based on Surface Plasmon Resonance

2003

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A study of the response behavior of saccharides to surface plasmon resonance (SPR) based sensor, in which a boronic acid membrane-modified thin gold film was used as a sensor chip is described. The following three procedures were used in the modification of the sensor chip: first, 3-aminophenylboronic acid (3-APB) was coupled with 11-mercaptoundecanoic acid to form a self-assembled monolayer (SAM) on the gold film of the sensor chip, second, 3-APB was immobilized on the sensor chip by electrochemical polymerization, and third, the sensor chip was coated with a vinyl polymer by the radical polymerization of vinylphenylboronic acid. SPR responses were measured in a flow system, where the above three types of sensor chip were assembled in the flow cell of the SPR sensor. The SPR responses caused by the interaction between the boronic acid membrane modified on the sensor chip and saccharides were evaluated by measurement of an angle shift of the SPR sensor. A weak response was observed for the SPR sensor using the sensor chip modified with SAM and the electropolymerized membrane, while the sensor chip modified with the vinylboronic acid polymer membrane showed a selective and enhanced response to saccharides. From the SPR response for the latter sensor, the findings indicate that the interaction between the boronic acid membrane on the sensor chip and the saccharides was in the order glucose < mannose < galactose < fructose. Namely, the interaction between the boronic acid and cis-diol moiety in the saccharides appears to be stronger in the order 2,3-cis-diol < 3,4-cis-diol < 1,2-cis-diol. The adsorption behavior of sorbose to the sensor chip modified with the boronic acid polymer membrane followed the Freundlich-type adsorption isotherm. The electrochemical polymerization of 3-APB on the gold film of the SPR sensor chip was monitored in situ by combining an SPR system with an electrochemical analyzer system.

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Section: Responses Of Spr Sensor With the Sensor Chipsupporting

confidence: 91%

“…Several fluorescent molecules, which contain a boronic acid moiety, have been successfully applied to the fluorometric sensing of saccharides [6 ± 8]. In our previous article, the interaction of monosaccharides with a solid suport modified with alkylboronic acid was evaluated using a liquid chromatographic method [9].…”

Section: Introductionmentioning

confidence: 99%

Modification of a Thin Gold Film with Boronic Acid Membrane and Its Application to a Saccharide Sensor Based on Surface Plasmon Resonance

2003

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“…However, the extraction of glucose was quite lower than that of C5 sugars. This fact is explained because the complexation constant with boronic acids is similar for xylose and arabinose and at the same time, higher than that for glucose. ,− A higher extraction of xylose and arabinose results in a higher ratio C5 sugars/glucose, which will probably give rise to a solution rich in pentitols after the final hydrogenation step.…”

Section: Resultsmentioning

confidence: 99%

From Biomass to Sugar Alcohols: Purification of Wheat Bran Hydrolysates Using Boronic Acid Carriers Followed by Hydrogenation of Sugars over Ru/H-ZSM-5

Sanchez‐Bastardo

Delidovich

Alonso

2018

ACS Sustainable Chem. Eng.

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Wheat bran is a lignocellulosic waste of milling industry. It contains hemicelluloses which can be valorized into arabitol and xylitol via a few-step approach. It begins with extraction and hydrolysis of hemicelluloses to produce a solution of xylose and arabinose along with proteins and inorganic salts. This work focusses on the purification of sugars of this hydrolysate and the subsequent catalytic production of sugar alcohols. A purification process based on the recovery of sugars by anionic extraction with a boronic acid, followed by back-extraction and a further refining step with ion exchange resins is described. After this process, a high purity sugars solution (~90%) free of inorganic elements and proteins was obtained. The feasibility of the process was also highlighted by a successful recycling of the organic phase containing the boronic acid. The hydrogenation of purified sugars was then performed over Ru/H-ZSM-5. A high yield into pentitols of ~70% with 100% selectivity was achieved. Importantly, the catalytic hydrogenation of sugars in the hydrolysate prior to purification did not occur. We determined that proteins caused the deactivation of the catalyst and consequently the inhibition of the production of sugar alcohols.

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“…Several buffer additives have been used to achieve a better separation for glycans: For glycan analysis, the effect of borate complexation was shown to have a considerable effect on the separation selectivity and resolution. The complexation by borate or boronic acids is due to the formation of five-or sixmembered rings involving the boron atom, two oxygens and two to three carbons [159,[168][169][170][171][172]. It was shown that the complexation is in the order: cis-1,2-diols>1,2-trans-diols.…”

Section: Capillary Electrophoresismentioning

confidence: 99%

Protein glycosylation analysis with capillary-based electromigrative separation techniques

Pattky

Hühn

2010

Bioanal Rev

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An impressive complexity is associated with glycoproteins due to the microheterogeneity of glycosylation as posttranslational modification giving rise to a vast number of isoforms. The full characterization of glycoproteins is difficult to achieve, and a number of analytical methods have to be combined for a detailed understanding of glycosylation. In this review, we focus on capillary electromigrative separation techniques in the formats capillary electrophoresis, micellar electrokinetic chromatography, and capillary sieving electrophoresis. These separation techniques can be applied to all levels of glycosylation analysis including intact glycoproteins, glycopeptides, and released glycans. We here discuss the separation characteristics for each method and the information that they can provide for each level. Detection issues, especially laser-induced fluorescence detection and mass spectrometry are taken into account. In addition, tables provide an overview on the achievements made from the very beginning of glycosylation research by electromigrative separation techniques. From the literature presented here it is clear, that glycosylation analysis by electromigrative separation techniques is on the edge of transition of basic research and method development towards applications. First proof-ofprinciple studies for in-depth glycoprotein characterization and clinical diagnosis are described. However, this overview also shows that many basic aspects of separation have not yet been fully understood and more research is necessary to be able to fully use the capabilities of electromigrative separation techniques.

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Evaluation of Interactions between Monosaccharides and a Stationary Phase Modified with Alkylboronic Acid by Means of a Liquid-Chromatographic Method

Cited by 7 publications

References 8 publications

Modification of a Thin Gold Film with Boronic Acid Membrane and Its Application to a Saccharide Sensor Based on Surface Plasmon Resonance

Modification of a Thin Gold Film with Boronic Acid Membrane and Its Application to a Saccharide Sensor Based on Surface Plasmon Resonance

From Biomass to Sugar Alcohols: Purification of Wheat Bran Hydrolysates Using Boronic Acid Carriers Followed by Hydrogenation of Sugars over Ru/H-ZSM-5

Protein glycosylation analysis with capillary-based electromigrative separation techniques

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