Click Reactions and Boronic Acids: Applications, Issues, and Potential Solutions

Dai, Chong; Cheng, Yunfeng; Cui, Jianmei; Wang, Binghe

doi:10.3390/molecules15085768

Cited by 39 publications

(26 citation statements)

References 83 publications

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“…Notably,t he VBA is not orthogonal to aC u I -mediated reaction between an azide and an alkyne owing to copper-mediated boronic acid degradation. [14] We used tetrazine-BODIPY probe 16 (Figure 3A and the Supporting Information, experimental section) to visualize the VBA-modified HSA protein. Complete conversion to the dihydropyridazine (HSA-DHP) product was observed by mass spectrometry (Supporting Information, Figure S14), and the appearance of ag reen fluorescent band was observed by fluorescence imaging of the SDS-PAGEgel (Figure 3C,a).…”

Section: Zuschriftenmentioning

confidence: 99%

Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

Eising¹,

Lelivelt²,

Bonger³

2016

Angewandte Chemie

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Bioorthogonal reactions are widely used for the chemical modification of biomolecules.T he application of vinylboronic acids (VBAs) as non-strained, synthetically accessible and water-soluble reaction partners in ab ioorthogonal inverse electron-demand Diels-Alder (iEDDA) reaction with 3,6-dipyridyl-s-tetrazines is described. Depending on the substituents,VBA derivatives give second-order rate constants up to 27 m À1 s À1 in aqueous environments at room temperature, which is suitable for biological labeling applications.T he VBAs are shown to be biocompatible,n on-toxic, and highly stable in aqueous media and cell lysate.F urthermore,V BAs can be used orthogonally to the strain-promoted alkyne-azide cycloaddition for protein modification, making them attractive complements to the bioorthogonal molecular toolbox.Inthe last decades,t he development of selective reactions between two reactants that are unaffected by any of the naturally occurring biological functionalities has been amajor research area in chemical biology.[1] These bioorthogonal reactions ( Figure 1A)m ake it possible to chemically modify biomolecules in their native cellular environment and gain ab etter understanding of their role in as pecific biological system or process.The bioorthogonal reaction should be high yielding and rapid, and the reactants and product(s) should be soluble and stable in aqueous media and non-toxic to the biological system. Theu se of small reactants is preferred to minimize steric interactions with the biomolecule or to facilitate incorporation by the endogenous cellular machinery.TheCarboni-Lindsey (CL) reaction between an electronpoor tetrazine ( Figure 1B, I)a nd an alkene has gained considerable attention for use in bioorthogonal applications. [2] As linear and unmodified alkenes ( Figure 1B, VI)s howed only poor reaction rates with tetrazines, [3] most research has been directed to the development and use of strained alkenes such as trans-cyclooctene (TCO), [4] norbornene, [5] cyclopropene, [6] or N-acylazetine [7] ( Figure 1B, II-V). In addition to strain, the rate of the CL reaction can be significantly enhanced by the introduction of electron-donating substituents on the alkene bond.[8] This aspect, however,h as been poorly investigated in relation to bioorthogonal applications.Vinylboronic acids ( Figure 1B, VII)a re an interesting class of compounds with unique electronic properties,w hich are due to their vacant p-orbital. As aresult of the inductive effect that is caused by the electronegativity difference of boron and carbon, the electronic deficiencyofboron and the electron-donating oxygens attached to boron, boronic acid is considered to be aw eak electron-donor.[9] Furthermore, boronic acids are mild organic Lewis acids,w hich in basic aqueous media are in equilibrium with their boronate anion ( Figure 1B, VIII), which is as trong electron-donor. [9] Although Diels-Alder reactions are known to proceed faster in aqueous media, the CL reactions of vinylboronic acids and alkylboronic acids are re...

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Section: Zuschriftenmentioning

confidence: 99%

Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

Eising¹,

Lelivelt²,

Bonger³

2016

Angewandte Chemie

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show abstract

“…A wide range of boronic acid probes for the detection and determination of monosaccharides in contact lens polymers have been developed [25]. In chemical biology, boronic acids are used in the detection and sensing of peroxides, recognition and sensing of the tetra serine motif in protein, development of new MRI contrast agents [26]. Also, boronic acid derivatives act as strong fluorescent sugar sensors.…”

Section: Introductionmentioning

confidence: 99%

Exploring the mechanism of fluorescence quenching in two biologically active boronic acid derivatives using Stern-Volmer kinetics

Geethanjali

Nagaraja

Melavanki

2015

Journal of Molecular Liquids

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“…Subsequently, the reactive fibres were subjected to CuAAc reaction with 1-ethynylpyrene under heterogeneous conditions at room temperature for 16 h, yielding photo-fibres. The chelating agent tris-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) was utilized together with copper sulphate in order to reduce the amount of catalyst, minimize unwanted side-reactions, and accelerate the CuAAc reaction (Dai, Cheng, Cui, & Wang, 2010). In addition to photo-fibres, three different blank samples were prepared by introducing the following variations on the original protocol used above: PF-B1, with no addition of 1-ethynylpyrene, PF-B2, using BKPP fibres instead of reactive fibres, PF-B3, BKPP fibres were used instead of reactive fibres and no 1-ethynylpyrene was added to the reaction medium.…”

Section: Characterization Of Photo-fibresmentioning

confidence: 99%

Preparation of reactive fibre interfaces using multifunctional cellulose derivatives

Vega

Wondraczek

Bretschneider

et al. 2015

Carbohydrate Polymers

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Click Reactions and Boronic Acids: Applications, Issues, and Potential Solutions

Cited by 39 publications

References 83 publications

Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni–Lindsey Reaction

Exploring the mechanism of fluorescence quenching in two biologically active boronic acid derivatives using Stern-Volmer kinetics

Preparation of reactive fibre interfaces using multifunctional cellulose derivatives

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