Bioconjugation of Peptides by Palladium-Catalyzed C−C Cross-Coupling in Water

Dibowski, Harald; Schmidtchen, Franz P.

doi:10.1002/(sici)1521-3773(19980302)37:4<476::aid-anie476>3.0.co;2-2

Cited by 102 publications

(46 citation statements)

References 2 publications

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“…Arguably, the most widely used TM-catalysed reactions in organic synthesis are the series of palladium-catalysed sp 2 -sp 2 coupling reactions between aryl/alkenyl halides and a variety of coupling partners such as boronic acids (Suzuki-Miyaura), alkenes (Mizoroki-Heck) and alkynes (Sonogashira). Early examples of couplings on short synthetic peptides required high temperatures, or the presence of organic solvents, yet demonstrated tolerance of Pd towards some amino-acid functional groups 116,117 . Despite the UAA p-iodophenylalanine having been incorporated into proteins by amber-stop codon suppression and proposed as a Pd coupling partner as early as 2002 (ref.…”

Section: Review Nature Communications | Doi: 101038/ncomms5740mentioning

confidence: 99%

Selective chemical protein modification

2014

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Section: Review Nature Communications | Doi: 101038/ncomms5740mentioning

confidence: 99%

Selective chemical protein modification

2014

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“…[37] This residue was reacted with several functionalized alkynes in an aqueous buffer using Pd(OAc) 2 , CuI, and guanidinophosphine as aw ater-soluble ligand. [37] This residue was reacted with several functionalized alkynes in an aqueous buffer using Pd(OAc) 2 , CuI, and guanidinophosphine as aw ater-soluble ligand.…”

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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“…Schmidtchen [191] has shown that Sonogashira couplings catalyzed by guanidinium substituted phosphines (TPPDG or TPPTG), in combination with palladium could be carried out under biocompatible conditions. When RNase A was added to the coupling reaction, no change in nuclease activity or electrophoretic behavior of the RNase was seen.…”

Section: Special Applications Of Aqueous-phase Catalystsmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

Shaughnessy¹,

DeVasher²

2005

COC

181

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Water has attracted significant attention as an alternative solvent for homogeneous metal-catalyzed reactions because it is a non-toxic, nonflammable solvent that can allow for simplified recovery of homogeneous catalysts. The use of water as a solvent in palladium-catalyzed cross-coupling reactions is of great academic and industrial interest. Palladium-catalyzed coupling reactions are powerful methods to make carbon-carbon and carbon-heteroatom bonds under mild conditions. Separation of the catalyst from the organic product can be very difficult; however, constraining the catalyst to the aqueous-phase of an aqueous-biphasic solvent system can potentially simplify catalyst recovery. This review will focus on recent developments in the design and application of aqueous-phase, palladium-catalyzed coupling reactions over the period from 2000, through late 2004. A variety of new hydrophilic ligand architectures have been introduced recently that provide significantly more active catalysts towards industrially relevant aryl bromides and chlorides. Stille CouplingRSiX3 L n Pd(Cat) Hiyama Coupling

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Bioconjugation of Peptides by Palladium-Catalyzed C−C Cross-Coupling in Water

Cited by 102 publications

References 2 publications

Selective chemical protein modification

Selective chemical protein modification

Palladium in the Chemical Synthesis and Modification of Proteins

Palladium-Catalyzed Cross-Coupling in Aqueous Media: Recent Progress and Current Applications

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