Palladium‐Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine‐Containing Molecules at Room Temperature

Al‐Shuaeeb, Riyadh Ahmed Atto; Kolodych, Sergii; Koniev, Oleksandr; Delacroix, Sébastien; Erb, Stéphane; Nicolaÿ, Stéphanie; Cintrat, Jean‐Christophe; Brion, Jean‐Daniel; Cianférani, Sarah; Alami, Mouâd; Wagner, Alain; Messaoudi, Samir

doi:10.1002/chem.201602277

Cited by 55 publications

(42 citation statements)

References 45 publications

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“…[172] Tr ansition metal-catalyzed arylation reactions have also been developed for cysteine bioconjugation. [173] Short, unprotected peptides could be converted into the corresponding S-aryl bioconjugates using only 2% of the palladium pre-catalyst in yields greater than 80 %. [173] Short, unprotected peptides could be converted into the corresponding S-aryl bioconjugates using only 2% of the palladium pre-catalyst in yields greater than 80 %.…”

Section: Angewandte Chemiementioning

confidence: 99%

Arylation Chemistry for Bioconjugation

et al. 2019

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Bioconjugation chemistry has been used to prepare modified biomolecules with functions beyond what nature intended. Central to these techniques is the development of highly efficient and selective bioconjugation reactions that operate under mild, biomolecule compatible conditions. Methods that form a nucleophile–sp2 carbon bond show promise for creating bioconjugates with new modifications, sometimes resulting in molecules with unparalleled functions. Here we outline and review sulfur, nitrogen, selenium, oxygen, and carbon arylative bioconjugation strategies and their applications to modify peptides, proteins, sugars, and nucleic acids

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Section: Angewandte Chemiementioning

confidence: 99%

Arylation Chemistry for Bioconjugation

et al. 2019

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“…2017 zeigten Buchwald, Hooker et al, dass eine effiziente Radiomarkierung ungeschützter Peptide durchgeführt werden kann, indem die enthaltenen Cysteine zunächst mit aus Dihalogenarenen erhaltenen Palladiumkomplexen aryliert und anschließend mit [ 11 C]Cyanid umgesetzt werden. [173] Mit nur 2% des Präkatalysators konnten kurze,u ngeschützte Peptide in Ausbeuten von über 80 %zud en entsprechenden S-Arylbiokonjugaten umgesetzt werden. [172] Fürd ie Cystein-Biokonjugation wurden weiterhin Übergangsmetall-katalysierte Arylierungsreaktionen entwickelt.…”

Section: Angewandte Chemieunclassified

Arylierungschemie für die Biokonjugation

et al. 2019

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Mittels Biokonjugationschemie können modifizierte Biomoleküle hergestellt werden, deren Funktionsumfang das natürliche Maß übersteigt. Hierbei ist die Entwicklung hocheffizienter und selektiver Biokonjugationsreaktionen von Bedeutung, die unter milden, biokompatiblen Bedingungen ablaufen. Vielversprechend sind hierbei Verfahren, bei denen Bindungen zwischen einem Nukleophil und einem sp2‐hybridisierten Kohlenstoffatom gebildet werden, wodurch in manchen Fällen Moleküle mit einzigartigen Eigenschaften erhalten werden können. In diesem Aufsatz werden Biokonjugationsstrategien für die Arylierung von Schwefel, Stickstoff, Selen, Sauerstoff und Kohlenstoff sowie ihre Anwendungen für die Modifikation von Peptiden, Proteinen, Kohlenhydraten und Nukleinsäuren zusammengefasst.

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“…[31][32] Cysteine modification employing palladium chemistry has also attracted several groups because of its robust nucleophi- licity and low abundance (ca. [35] This complex enabled, in organic and aqueous solvents,cysteine conjugation with either aryl or alkyne halides in the presence of av ariety of functional groups,a nd was applied for the efficient bioconjugation of peptides and proteins with various tags to give the product in 80-99 %y ield. Recently the groups of Buchwald and Pentelute reported adirect approach for modifying acysteine within unprotected polypeptides by employing organopalladium species prepared from PdCl 2 and functionalized with an aryl halide and the 2-dicyclohexylphosphino-2,6-diisopropoxybiphenyl (Ru-Phos) ligand ( Figure 2B).…”

Section: Palladium-assisted In Vitro Protein Modificationsmentioning

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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Palladium‐Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine‐Containing Molecules at Room Temperature

Cited by 55 publications

References 45 publications

Arylation Chemistry for Bioconjugation

Arylation Chemistry for Bioconjugation

Arylierungschemie für die Biokonjugation

Palladium in the Chemical Synthesis and Modification of Proteins

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