Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.
@article{Henry2014AminoAB, 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}, year={2014}, volume={50 99}, pages={ 15692-5 } }
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).
- ChemistryDalton transactions
- 2015
Isolation of digold triazolate complexes offer compelling support for the role of two copper(i) ions in CuAAC, and rate inhibition by the addition of free triphenylphosphine to the reaction indicates that ligand dissociation is a prerequisite for the reaction.
IClick cycloaddition reaction of light-triggered manganese(I) carbonyl complexes
- Chemistry
- 2018
Mono- and binuclear blue-light-induced CO-releasing molecules based on a fac-MnBr(CO)3 moiety and bearing benzimidazole ligands furnished with either a sulfonate or phosphonium group were…
Catalyst-free room-temperature iClick reaction of molybdenum(ii) and tungsten(ii) azide complexes with electron-poor alkynes: structural preferences and kinetic studies.
- ChemistryDalton transactions
- 2017
Two isostructural and isoelectronic group VI azide complexes of the general formula [M(η3-allyl)(N3)(bpy)(CO)2] with M = Mo, W and bpy = 2,2'-bipyridine were prepared and fully characterized,…
SPAAC iClick: progress towards a bioorthogonal reaction in-corporating metal ions.
- ChemistryDalton transactions
- 2021
Combining strain-promoted azide-alkyne cycloaddition (SPAAC) and inorganic click (iClick) reactivity provides access to metal 1,2,3-triazolates by demonstrating iClick reactivity depends on the accessibility of the azide functionality rather than electronic effects imparted by the metal.
Electronic Influences on the Stability and Kinetics of Cp* Rhodium(III) Azide Complexes in the iClick Reaction with Electron‐Poor Alkynes
- Chemistry
- 2017
Rhodium(III) azide half-sandwich complexes of general formula [Rh(Cp*)(N3)(bpyR,R)]CF3SO3 with R = H, OCH3 were prepared in three steps in an overall yield of 55–65 %. Their stability strongly…
Azide Chemistry – An Inorganic Perspective, Part II[‡] [3+2]-Cycloaddition Reactions of Metal Azides and Related Systems†
- Chemistry
- 2015
In whatever state of bonding – whether covalent to an organic residue or a heteroatom, or polar to ionic in contact with a metal – the azide moiety N3 is characterized by its high potential of…
2,2':6',2''-Terpyridine switches from tridentate to monodentate coordination in a gold(iii) terpy complex upon reaction with sodium azide.
- ChemistryChemical communications
- 2019
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.
Crystallographic signatures of silver-purine frameworks with an azide functionality
- Materials Science
- 2016
Single versus Double Cu(I) Catalyzed [3 + 2] Azide/Platinum Diacetylide Cycloaddition Reactions
- Chemistry
- 2017
This report focuses on Cu(I) catalyzed cycloaddition reactions between organic azides and the platinum diacetylide complexes trans-(PR3)2Pt(C≡CR′)2 (where PR3 = P(OEt)3, PEt3, PnBu3, PPhMe2, PPh3,…
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