Aqueous Oxidative Heck Reaction as a Protein‐Labeling Strategy

Ourailidou, Maria E.; Meer, Jan-Ytzen van der; Baas, Bert‐Jan; Jeronimus-Stratingh, Margot; Gottumukkala, Aditya L.; Poelarends, Gerrit J.; Minnaard, Adriaan J.; Dekker, Frank J.

doi:10.1002/cbic.201300714

Cited by 46 publications

(53 citation statements)

References 22 publications

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“…Myers and co-workers reported ahighly effective Heck cross-coupling reaction, in aqueous buffers, with proteins bearing an olefin handle,t og ive the desired product in good yields (ca. [51] This strategy enabled the conjugation of several boronic acid derivatives using ab asefree system and Pd(OAc) 2 complexed with ab is(imine), acenaphthenequinone and mesitylamine,l igand under aerobic conditions. [49] Theo lefin functionality was incorporated into the side chain of alysine residue,which was coupled with functionalized N-hydroxysuccinimide.T he tagged protein was coupled by palladium complexes,w hich were prepared by decarboxylative palladation of electronrich benzoic acid derivatives bearing various functional groups and palladium(II) trifluoroacetate [Pd(TFA) 2 ].…”

Section: Methodsmentioning

confidence: 99%

Palladium in the Chemical Synthesis and Modification of Proteins

2017

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The field of site-specific modification of proteins has drawn significant attention in recent years owing to its importance in various research areas such as the development of novel therapeutics and understanding the biochemical and cellular behaviors of proteins. The presence of a large number of reactive functional groups in the protein of interest and in the cellular environment renders modification at a specific site a highly challenging task. With the development of sophisticated chemical methodologies it is now possible to target a specific site of a protein with a desired modification, however, many challenges remain to be solved. In this context, transition metals in particular palladium-mediated C-C bond-forming and C-O bond-cleavage reactions gained great interest owing to the unique catalytic properties of palladium. Palladium chemistry is being explored for protein modifications in vitro, on the cell surface, and within the cell. Very recently, palladium complexes have been applied for the rapid deprotection of several widely utilized cysteine protecting groups as well as in the removal of solubilizing tags to facilitate chemical protein synthesis. This Minireview highlights these advances and how the accumulated knowledge of palladium chemistry for small molecules is being impressively transferred to synthesis and modification of chemical proteins.

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Section: Methodsmentioning

confidence: 99%

Palladium in the Chemical Synthesis and Modification of Proteins

2017

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“…Dekker und Mitarbeiter passten die oxidative Heck-Reaktion, [83] ein unter aeroben Bedingungen zwischen Alkenen und Arylboronsäuren ablaufender Prozess,e iner bioorthogonalen Reaktion an (Schema 21). Der Katalysator wurde aus Pd(OAc) 2 und dem Liganden Bis(aryl)acenaphthechinondiimin (BIAN) gebildet und wies eine geringe Lçslichkeit in Wasser auf,s odass eine Mischung aus Puffer und DMF (6:1) als Lçsungsmittel nçtig war.…”

Section: Oxidative Heck-reaktionunclassified

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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“…The formation of succinimide thioethers via thiol 1,4‐addition is frequently used to form bioconjugates or to immobilize bioactive compounds on surfaces . It is the preferred method for the formation of antibody‐drug conjugates .…”

Section: Introductionmentioning

confidence: 99%

The stereodynamics of macrocyclic succinimide‐thioethers

Lenz

Horx

Geyer

2018

Journal of Peptide Science

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Maleimide-thiol coupling is a popular bioconjugation strategy, but little is known about the stereoselectivity and the stereodynamics of the succinimide thioether formed in a biopolymer environment. We used thiol 1,4-addition for the macrocyclisation of 5 designed pentapeptides with the ringsize of hexapeptides because they incorporate the succinimide thioether (4-8). Both succinimide diastereomers are observed in the constrained macrocyclic rings in each case. In spite of the low diastereoselectivity of the macrocyclisation reaction, there is a significant influence of the amino acid environment on the epimerization rate of the succinimide. Its half life can be as short as several hours at room temperature when Gly is the amino acid following the succinimide (peptide 8). On the contrary, no epimerization is detectable even after several weeks in the case of d-Phe C-terminal to the succinimide in peptide 4. Already the small selection of examples shows how big the differences in epimerization rates can be and that the local environment has a significant influence. The variation of amino acids in the vicinity of the ligation site points the way towards the synthesis of bioconjugates which are obtained as stable and separable diastereomers.

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Aqueous Oxidative Heck Reaction as a Protein‐Labeling Strategy

Cited by 46 publications

References 22 publications

Palladium in the Chemical Synthesis and Modification of Proteins

Palladium in the Chemical Synthesis and Modification of Proteins

Boronsäuren als bioorthogonale Sonden für zentrenselektives Protein‐Labeling

The stereodynamics of macrocyclic succinimide‐thioethers

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