Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH

Ni, Nanting; Laughlin, Sarah; Ying-ji, Wang; Feng, You; Zheng, Y. George; Wang, Binghe

doi:10.1016/j.bmc.2012.03.014

Cited by 45 publications

(26 citation statements)

References 30 publications

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“…The time constant for glucose transport through the flow cell, estimated via simulation of convective–diffusive mass transfer (under conditions used in the tests and with a glucose diffusivity of 4.5 × 10 −11 m 2 /s), was approximately 1.5 min and comparable to the time constants of the measurement data. On the other hand, the time constant for glucose diffusion through the hydrogel, estimated via one-dimensional diffusion (under conditions used in the tests and with a glucose diffusivity of 4.5 × 10 −11 m 2 /s), was approximately 1.2 s and the glucose-boronic acid binding was expected to be as fast as milliseconds (Ni et al 2012). These two latter time scales were both substantially smaller than the time constants of the measurement data.…”

Section: Resultsmentioning

confidence: 99%

A dielectric affinity glucose microsensor using hydrogel-functionalized coplanar electrodes

Zhang

Maturavongsadit

Shang

et al. 2017

Microfluid Nanofluid

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This paper presents a dielectric affinity microsensor that consists of an in situ prepared hydrogel attached to a pair of coplanar electrodes for dielectrically based affinity detection of glucose in subcutaneous tissue in continuous glucose monitoring applications. The hydrogel, incorporating N-3-acrylamidophenylboronic acid that recognizes glucose via affinity binding, is synthetically prepared on the electrodes via in situ gelation. When implanted in subcutaneous tissue, glucose molecules in interstitial fluid diffuse rapidly through the hydrogel and bind to the phenylboronic acid moieties. This induces a change in the hydrogel’s permittivity and hence in the impedance between the electrodes, which can be measured to determine the glucose concentration. The in situ hydrogel preparation allows for a reduced hydrogel thickness (~10 μm) to enable the device to respond rapidly to glucose concentration changes in tissue, as well as covalent electrode attachment of the hydrogel to eliminate the need for semipermeable membranes that would otherwise be required to restrain the sensing material within the device. Meanwhile, the use of coplanar electrodes is amenable to the in situ preparation and facilitates glucose accessibility of the hydrogel, and combined with dielectrically based transduction, also eliminates mechanical moving parts often found in existing affinity glucose microsensors that can be fragile and complicated to fabricate. Testing of the device in phosphate-buffered saline at pH 7.4 and 37 °C has shown that at glucose concentrations ranging from 0 to 500 mg/dL, the hydrogel-based microsensor exhibits a rapid, repeatable, and reversible response. In particular, in the glucose concentration range of 40–100 mg/dL, which is of great clinical interest to monitoring normal and low blood sugar levels, the device response is approximately linear with a resolution of 0.32 mg/dL based on effective capacitance and 0.27 mg/dL based on effective resistance, respectively. Thus, the device holds the potential to enable reliable and accurate continuous monitoring of glucose in subcutaneous tissue.

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Section: Resultsmentioning

confidence: 99%

A dielectric affinity glucose microsensor using hydrogel-functionalized coplanar electrodes

Zhang

Maturavongsadit

Shang

et al. 2017

Microfluid Nanofluid

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“…The reaction between boronic acid and sugars has been extensively studied (49,51) and it has been established that boronic acid can form reversible covalent bonds with sugars under basic conditions which can be broken in acidic solutions. To obtain the most effective and comprehensive enrichment of glycopeptides from yeast whole cell lysates, several experimental parameters were optimized.…”

Section: Resultsmentioning

confidence: 99%

A Universal Chemical Enrichment Method for Mapping the Yeast N-glycoproteome by Mass Spectrometry (MS)

Chen

Smeekens

2014

Molecular & Cellular Proteomics

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Glycosylation is one of the most common and important protein modifications in biological systems. Many glycoproteins naturally occur at low abundances, which makes comprehensive analysis extremely difficult. Additionally, glycans are highly heterogeneous, which further complicates analysis in complex samples. Lectin enrichment has been commonly used, but each lectin is inherently specific to one or several carbohydrates, and thus no single or collection of lectin(s) can bind to all glycans. Here we have employed a boronic acid-based chemical method to universally enrich glycopeptides. The reaction between boronic acids and sugars has been extensively investigated, and it is well known that the interaction between boronic acid and diols is one of the strongest reversible covalent bond interactions in an aqueous environment. This strong covalent interaction provides a great opportunity to catch glycopeptides and glycoproteins by boronic acid, whereas the reversible property allows their release without side effects. More importantly, the boronic acid-diol recognition is universal, which provides great capability and potential for comprehensively mapping glycosylation sites in complex biological samples. By combining boronic acid enrichment with PNGase F treatment in heavy-oxygen water and MS, we have identified 816 N-glycosylation sites in 332 yeast proteins, among which 675 sites were well-localized with greater than 99% confidence. The results demonstrated that the boronic acid-based chemical method can effectively enrich glycopeptides for comprehensive analysis of protein glycosylation. A general trend seen within the large data set was that there were fewer glycosylation sites toward the C termini of proteins. Of the 332 glycoproteins identified in yeast, 194 were membrane proteins. Many proteins get glycosylated in the high-mannose N-glycan biosynthetic and GPI anchor biosynthetic pathways. Compared with lectin enrichment, the current method is more cost-efficient, generic, and effective. This method can be extensively applied to different complex samples for the comprehensive analysis of protein glycosylation. Molecular &

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“…Binding constant (M À1 ) References 1419 [48] 175.1 [49] 2170 [50] 237 [51] 46 [52] 526.3 [53] 1538 [54] 476 [55] 1000 [56,57] 120 [40] 3582.88 Present work coefficient of R = 0.98 . The linear regression equation was determined to be (I 0 -I)/I 0 = 0.012 Â 10 5 c + 0.033, where c is the concentration of D-fructose.…”

Section: Boronic Acid Receptormentioning

confidence: 99%

A new boronic acid fluorescent sensor based on fluorene for monosaccharides at physiological pH

Hosseinzadeh

Mohadjerani

Pooryousef

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH

Cited by 45 publications

References 30 publications

A dielectric affinity glucose microsensor using hydrogel-functionalized coplanar electrodes

A dielectric affinity glucose microsensor using hydrogel-functionalized coplanar electrodes

A Universal Chemical Enrichment Method for Mapping the Yeast N-glycoproteome by Mass Spectrometry (MS)

A new boronic acid fluorescent sensor based on fluorene for monosaccharides at physiological pH

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