Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.

  title={Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.},
  author={Lucas Henry and Christoph Schneider and Benedict M{\"u}tzel and Peter V. Simpson and Christopher J. Nagel and Katharina Fucke and Ulrich Schatzschneider},
  journal={Chemical communications},
  volume={50 99},
The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity. 
27 Citations

Au-iClick mirrors the mechanism of copper catalyzed azide-alkyne cycloaddition (CuAAC).

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Electronic Influences on the Stability and Kinetics of Cp* Rhodium(III) Azide Complexes in the iClick Reaction with Electron‐Poor Alkynes

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X-ray structure analysis showed that the isolated product is [Au(N3)3(terpy-κ1-N1)], in which the terpyridine ligand is in a very rare monodentate coordination mode, and this is also the dominant species in solution.

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This concept sketches the potential of these reactions not only to prepare "a la carte" multimetal 1,2,3-triazole derivatives, but also to discover new and unprecedented reactions.

The hydrazide/hydrazone click reaction as a biomolecule labeling strategy for M(CO)3 (M = Re, (99m)Tc) radiopharmaceuticals.

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Results suggest that a successful cycloaddition reaction between a metal-azide complex and anAlkyne substrate is dependent both on the ligand and metal oxidation state, that determine the electronic properties of the bound azide, as well as the electron deficient nature of the alkyne employed.

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The basis for the unique properties and rate enhancement for triazole formation under Cu(1) catalysis should be found in the high ∆G of the reaction in combination with the low character of polarity of the dipole of the noncatalyzed thermal reaction, which leads to a considerable activation barrier.