Sugar complexation to silicone boronic acids

Brook, Michael A.; Dodge, Laura; Yang, Chen; Gonzaga, Ferdinand; Amarne, Hazem

doi:10.1039/c2cc37438b

Cited by 18 publications

(30 citation statements)

References 15 publications

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“…Self‐healing, which describes the ability of artificial systems to repair their damage spontaneously, is an especially interesting property of these materials . Endowing polysiloxane‐based materials with superior properties, such as self‐healing, could greatly expand their applications . Various efforts have been made to explore novel self‐healing systems in polymer or materials science .…”

Section: Methodsmentioning

confidence: 99%

Polysiloxane‐Based Autonomic Self‐Healing Elastomers Obtained through Dynamic Boronic Ester Bonds Prepared by Thiol–Ene “Click” Chemistry

Zuo

Gou

Zhang

et al. 2016

Macromol. Rapid Commun.

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Cross-linked silicone elastomers constructed with dynamic-covalent boronic esters are first synthesized by photoinitiated radical thiol-ene "click" chemistry. The resultant samples can be cut with a sharp knife into two pieces and then healed via the reversibility of the boronic ester cross-linkages to restore the original silicone sample within 30 min. Regulation of luminescent properties is achieved by incorporating organic dye into the elastomers through a "one-pot" thiol-ene reaction. The proposed synthesis procedure demonstrates a new strategy to produce boronic acid silicone materials capable of self-healing without external forces.

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Section: Methodsmentioning

confidence: 99%

Polysiloxane‐Based Autonomic Self‐Healing Elastomers Obtained through Dynamic Boronic Ester Bonds Prepared by Thiol–Ene “Click” Chemistry

Zuo

Gou

Zhang

et al. 2016

Macromol. Rapid Commun.

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“…Silicone boronate ester polymers SiBA were synthesised according to a published procedure24 that was adapted to provide gram quantities of these materials. Synthesis involved the platinum‐catalysed hydrosilylation of p ‐vinylphenylboronic acid dimethyl‐ L ‐tartrate ester with HMeSi‐containing silicone polymers of various molecular weights.…”

Section: Resultsmentioning

confidence: 99%

“…However, coordination of nitrogen25 or other Lewis bases, such as hydroxide,26 to these molecules to give a tetrahedral geometry about boron leads to a significant shift to approximately 10 ppm. A model compound PMDS‐BA (Figure 1), derived from pentamethyldisiloxane,24 was treated with ethylenediamine in the absence of other Lewis bases. It is clear from the change in chemical shift of about −23 ppm that the boron atom of PMDS‐BA is participating in Lewis acid–base complexation with ethylenediamine in solution (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Previously, we described the preparation of silicone boronic acids and their esters with α,ω‐telechelic structures SiBA (Figure 1). 24 We report that these and related structures efficiently lead under mild conditions to responsive, reversible elastomers resulting from Lewis acid–Lewis base interactions with amine‐bearing small molecules and polymers.…”

Section: Introductionmentioning

confidence: 97%

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Silicone Boronates Reversibly Crosslink Using Lewis Acid– Lewis Base Amine Complexes

Dodge

Chen

Brook

2014

Chemistry A European J

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Silicone elastomers are normally thermosets, which are not readily recycled or repurposed. The few examples of thermoplastic silicone elastomers depend on reversible covalent and non-covalent molecular interactions. It is demonstrated that amine-boronate complex formation provides a simple and flexible route to reversible crosslinked silicones. A variety of network structures were prepared by use of terminal and pendantly functionalised silicone boronates and amines. The crosslink density was quantified using a combination of Shore-hardness measurements, swelling, and rheological analyses. Stress induced by compressive force could be relieved through dynamic B-N bond reformation at 60 °C. Materials could be fully disassembled through introduction of n-butylamine and successfully reformed upon removal of the monofunctional amine by evaporation.

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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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Sugar complexation to silicone boronic acids

Cited by 18 publications

References 15 publications

Polysiloxane‐Based Autonomic Self‐Healing Elastomers Obtained through Dynamic Boronic Ester Bonds Prepared by Thiol–Ene “Click” Chemistry

Polysiloxane‐Based Autonomic Self‐Healing Elastomers Obtained through Dynamic Boronic Ester Bonds Prepared by Thiol–Ene “Click” Chemistry

Silicone Boronates Reversibly Crosslink Using Lewis Acid– Lewis Base Amine Complexes

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

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