Developments in the Field of Bioorthogonal Bond Forming Reactions—Past and Present Trends

King, Mathias; Wagner, Alain

doi:10.1021/bc500028d

Cited by 132 publications

(95 citation statements)

References 230 publications

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“…[2] As a result, only a hand-ful of reactions have been developed that fulfil all of these criteria. [3] Among them, the Staudinger ligation (azide-phosphine), copper-catalysed or strain-promoted azide-alkyne cycloadditions and tetrazine ligation approaches are the most widely utilised bioorthogonal reactions to date. [4] While these transformations have been helpful addressing a number of fundamental biological questions, [1b,5] toxicity, cross-reactivity with endogenous thiols or other biomolecules, and poor stability of the reagents in biological environments, complicate their application in a number of settings.…”

Section: Introductionmentioning

confidence: 99%

PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

Dumas¹,

Peramo

Desmaële

et al. 2016

Chimia

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Chemical transformations that can be performed selectively under physiological conditions are highly desirable tools to track biomolecules and manipulate complex biological processes. Here, we report a new nanocatalyst consisting of small palladium nanoparticles stabilized on the surface of PLGA-PEG nanoparticles that show excellent catalytic activity for the modification of biological building blocks through Suzuki-Miyaura cross-coupling reactions in water. Brominated or iodinated amino acids were coupled with aryl boronic acids in phosphate buffer in good yields. Interestingly, up to 98% conversion into the coupled amino acid could be achieved in 2 h at 37 °C using the stable, water-soluble cyclic triolborate as organometallic partner in the presence of only 1 mol% of palladium. These results pave the way for the modification of biomolecules in complex biological systems such as the intracellular space.

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Section: Introductionmentioning

confidence: 99%

PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

Dumas¹,

Peramo

Desmaële

et al. 2016

Chimia

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“…From its very first development the Staudinger-Bertozzi ligation has been successfully employed in biochemistry to immobilize peptides and proteins onto different materials, [18][19][20][21][22] for in vivo and in vitro imaging, and for protein detection. [23][24][25] This reaction seems to be an ideal candidate for designing a new AuNP template that can react in a highly chemoselective and efficient way with any azide-modified (bio)molecule. For these reasons we report the synthesis of a thiol ligand that contains a methyl-2-(diphenylphosphino)benzoate moiety designed to undergo a Staudinger-Bertozzi ligation with azide functionalities.…”

mentioning

confidence: 99%

Small gold nanoparticles for interfacial Staudinger–Bertozzi ligation

et al. 2015

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Small gold nanoparticles (AuNPs) that possess interfacial methyl-2-(diphenylphosphino)benzoate moieties have been successfully synthesized (Staudinger-AuNPs) and characterized by multi-nuclear MR spectroscopy, transmission electron microscopy (TEM), UV-Vis spectroscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy (XPS). In particular, XPS was remarkably sensitive for characterization of the novel nanomaterial, and in furnishing proof of its interfacial reactivity. These Staudinger-AuNPs were found to be stable to the oxidation of the phosphine center. The reaction with benzyl azide in a Staudinger-Bertozzi ligation, as a model system, was investigated using (31)P NMR spectroscopy. This demonstrated that the interfacial reaction was clean and quantitative. To showcase the potential utility of these Staudinger-AuNPs in bioorganic chemistry, a AuNP bioconjugate was prepared by reacting the Staudinger-AuNPs with a novel azide-labeled CRGDK peptide. The CRGDK peptide could be covalently attached to the AuNP efficiently, chemoselectively, and with a high loading.

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“…[2][3][4] In 2000, the so-called traceless variant was developed independently by Raines 5 and Bertozzi 6 and it is among the most powerful bioorthogonal ligation reactions. [7][8][9] Due to the mild reaction conditions and the formation of an amide (peptide) bond, 10 this Staudinger approach has found various applications, e.g. the labeling of bioactive molecules with fluorescence dyes 11 as well as radionuclides, [12][13][14] the chemoselective modification of peptides 5,15,16 and proteins, 17,18 the modification of polymers, 19 the preparation of special lactams, 20,21 or the synthesis of glycosyl amides.…”

mentioning

confidence: 99%

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

Mamat

Köckerling

2014

Synthesis

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Functionalized phosphane-containing key building blocks were synthesized that are suitable for the labeling of biologically active molecules by the traceless Staudinger ligation. Thus, a 2-(diphenylphosphanyl)phenyl 4-stannylbenzoate building block was converted into the 4-iodobenzoate by the introduction of iodine. The traceless Staudinger ligation was used to introduce the resulting 4-iodobenzoate moiety into selected molecules of pharmacological interest. Furthermore, the labeling procedure was used to insert the 4-iodobenzoate moiety into a peptide on solid support. Finally, a convenient recovery procedure of the key phosphane building block 2-(diphenylphosphanyl)phenol from 2-(diphenylphosphoryl)phenol was evaluated.

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Developments in the Field of Bioorthogonal Bond Forming Reactions—Past and Present Trends

Abstract: In response to the ever increasing need of chemical biology for new tools, a wide variety of new, highly selective reactions have been described. Herein we report a summary of recent developments and the historical background on bioorthogonal ligation reactions.

Cited by 132 publications

References 230 publications

PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

Small gold nanoparticles for interfacial Staudinger–Bertozzi ligation

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

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