Vinylboronic Acids as Efficient Bioorthogonal Reactants for Tetrazine Labeling in Living Cells

Eising, Selma; Linden, Nicole G. A. van der; Kleinpenning, Fleur; Bonger, Kimberly M.

doi:10.1021/acs.bioconjchem.7b00796

Cited by 22 publications

(17 citation statements)

References 38 publications

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“…These alkenes are easily accessible, biocompatible with cellular components, highly soluble, and stable in aqueous media and in cell lysates. Furthermore, VBAs are suitable as bioorthogonal reactants in tetrazine ligation for the labelling of proteins in vitro and in living cells …”

Section: Methodsmentioning

confidence: 99%

Coordination‐Assisted Bioorthogonal Chemistry: Orthogonal Tetrazine Ligation with Vinylboronic Acid and a Strained Alkene

Eising¹,

Xin

Kleinpenning³

et al. 2018

ChemBioChem

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Bioorthogonal chemistry can be used for the selective modification of biomolecules without interfering with any other functionality that might be present. Recent developments in the field include orthogonal bioorthogonal reactions to modify multiple biomolecules simultaneously. During our research, we observed that the reaction rates for the bioorthogonal inverse-electron-demand Diels-Alder (iEDDA) reactions between nonstrained vinylboronic acids (VBAs) and dipyridyl-s-tetrazines were exceptionally higher than those between VBAs and tetrazines bearing a methyl or phenyl substituent. As VBAs are mild Lewis acids, we hypothesised that coordination of the pyridyl nitrogen atom to the boronic acid promoted tetrazine ligation. Herein, we explore the molecular basis and scope of VBA-tetrazine ligation in more detail and benefit from its unique reactivity in the simultaneous orthogonal tetrazine labelling of two proteins modified with VBA and norbornene, a widely used strained alkene. We further show that the two orthogonal iEDDA reactions can be performed in living cells by labelling the proteasome by using a nonselective probe equipped with a VBA and a subunit-selective VBA bearing a norbornene moiety.

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Section: Methodsmentioning

confidence: 99%

Coordination‐Assisted Bioorthogonal Chemistry: Orthogonal Tetrazine Ligation with Vinylboronic Acid and a Strained Alkene

Eising¹,

Xin

Kleinpenning³

et al. 2018

ChemBioChem

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“…Introduction of a carbamate in allylic position to the double bond of a trans ‐cyclooctene allows for “click‐to‐release” reactions, opening up the possibility for targeted drug delivery . The use of vinylboronic acids can lead to high selectivity towards 2‐pyridyl or 2‐hydroxyphenyl substituted 1,2,4,5‐tetrazines, as recently shown by Bonger and co‐workers. Other bioorthogonal ligations based on aza‐Diels–Alder reactions include the 1,2,4‐triazine ligation introduced by Prescher and co‐workers and a variant of the Kondrat′eva reaction introduced by Jouanno et al.…”

Section: Introductionmentioning

confidence: 89%

Factors Controlling the Diels–Alder Reactivity of Hetero‐1,3‐Butadienes

et al. 2018

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We have quantum chemically explored the Diels–Alder reactivities of a systematic series of hetero‐1,3‐butadienes with ethylene by using density functional theory at the BP86/TZ2P level. Activation strain analyses provided physical insight into the factors controlling the relative cycloaddition reactivity of aza‐ and oxa‐1,3‐butadienes. We find that dienes with a terminal heteroatom, such as 2‐propen‐1‐imine (NCCC) or acrolein (OCCC), are less reactive than the archetypal 1,3‐butadiene (CCCC), primarily owing to weaker orbital interactions between the more electronegative heteroatoms with ethylene. Thus, the addition of a second heteroatom at the other terminal position (NCCN and OCCO) further reduces the reactivity. However, the introduction of a nitrogen atom in the backbone (CNCC) leads to enhanced reactivity, owing to less Pauli repulsion resulting from polarization of the diene HOMO in CNCC towards the nitrogen atom and away from the terminal carbon atom. The Diels–Alder reactions of ethenyl‐diazene (NNCC) and 1,3‐diaza‐butadiene (NCNC), which contain heteroatoms at both the terminal and backbone positions, are much more reactive due to less activation strain compared to CCCC.

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“…[86] Die Proteasommarkierung wurde mittels einer zweistufigen Labeling-Strategie durchgeführt. [86] Die Proteasommarkierung wurde mittels einer zweistufigen Labeling-Strategie durchgeführt.…”

Section: Diels-alder-reaktion Mit Inversem Elektronenbedarf (Iedda): unclassified

Boronsäuren als bioorthogonale Sonden für zentrenselektives Protein‐Labeling

Akgun¹,

Hall²

2018

Angewandte Chemie

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In den vergangenen zwei Jahrzehnten hat sich die bioorthogonale Chemie zu einem beliebten Hilfsmittel entwickelt, um zentrenselektive Modifikationen an Proteinen zu erzielen. Dennoch sind nur einige wenige bioorthogonale Reaktionen bekannt, die zudem Limitierungen aufweisen können, wie etwa geringe Reaktionsgeschwindigkeiten, die Verwendung instabiler oder zytotoxischer Reagenzien und das Auftreten von Nebenreaktionen. Folglich besteht ein großes Interesse an der Erweiterung der Methodik in der bioorthogonalen Chemie. In diesem Zusammenhang wurden kürzlich Boronsäuren in den Bereich der bioorthogonalen Chemie eingeführt, welche in drei verschiedenen Strategien zum Einsatz kommen: 1) Bildung eines Boronsäureesters zwischen der Boronsäure und einem 1,2‐cis‐Diol; 2) Bildung eines Iminoboronates zwischen 2‐Acetyl‐/Formyl‐Arylboronsäure und Hydrazin‐/Hydroxylamin‐/Semicarbazid‐Derivaten; 3) Verwendung einer Boronsäure als Transfergruppe in einer Suzuki‐Miyaura‐Kreuzkupplung oder einer anderen Reaktion, in deren Verlauf die Boronylgruppe das Intermediat verlässt. In diesem Aufsatz fassen wir die Fortschritte der Anwendung von Boronsäuren in der bioorthogonalen Chemie zusammen, welche das zentrenspezifische Labeling von Proteinen ermöglicht, und vergleichen diese Methoden mit den gängigsten bioorthogonalen Reaktionen.

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Vinylboronic Acids as Efficient Bioorthogonal Reactants for Tetrazine Labeling in Living Cells

Cited by 22 publications

References 38 publications

Coordination‐Assisted Bioorthogonal Chemistry: Orthogonal Tetrazine Ligation with Vinylboronic Acid and a Strained Alkene

Coordination‐Assisted Bioorthogonal Chemistry: Orthogonal Tetrazine Ligation with Vinylboronic Acid and a Strained Alkene

Factors Controlling the Diels–Alder Reactivity of Hetero‐1,3‐Butadienes

Boronsäuren als bioorthogonale Sonden für zentrenselektives Protein‐Labeling

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