We present a bioorthogonal and modular conjugation method for efficient coupling of organic dyes and biomolecules to quantum dots (QDs) using a norbornene-tetrazine cycloaddition. The use of noncoordinating functional groups combined with the rapid rate of the cycloaddition leads to highly efficient conjugation. We have applied this method to the in situ targeting of norbornene-coated QDs to li...

The ligand 3-chloro-6-dipicolylamino-1,2,4,5-tetrazine (Cl-TTZ-dipica) , prepared by the direct reaction between 3,6-dichloro-1,2,4,5-tetrazine and di(2-picolyl)-amine, afforded a series of four neutral transition metal complexes formulated as [Cl-TTZ-dipica-MCl2]2, with M = Zn(II), Cd(II), Mn(II) and Co(II), when reacted with the corresponding metal chlorides. The dinuclear structure of the is...

There is considerable interest in the use of bioorthogonal covalent chemistry, such as “click” reactions, to label small molecules located on live or fixed cells. Such labeling has been used for the visualization of glycans, activity-based protein profiling, the site-specific tagging of proteins, the detection of DNA and RNA synthesis, investigation of the fate of small molecules in plants, and...

The bioorthogonal reaction between tetrazines and trans-cyclooctenes is a method for the rapid construction of F-18 probes for PET imaging. Described here is a second generation (18)F-labeling system based on a conformationally strained trans-cyclooctene (sTCO)-a dienophile that is approximately 2 orders of magnitude more reactive than conventional TCO dienophiles. Starting from a readily prepa...

The ability to post-synthetically functionalize conjugated polymers by “plugging” various structures into the polymer backbone is demonstrated in Research Article on page 2980 Alex Adronov and co-workers using inverse-electron-demand Diels–Alder (IEDDA) chemistry a poly(tetrazine) backbone. A small library of was rapidly prepared reacting series trans-cyclooctyne derivatives with poly(tetrazine).

We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels-Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethyls...

We developed a new fluorogenic bioorthogonal reaction that is based on the inverse electron-demand Diels-Alder reaction between styrene (an unstrained alkene) and a simple tetrazine. The reaction forms a new fluorophore with no literature precedent. We have identified an aminoacyl-tRNA synthetase/tRNA pair for the efficient and site-specific incorporation of a styrene-containing amino acid into...

A first-of-its-kind (18)F pretargeted PET imaging approach based on the bioorthogonal inverse electron demand Diels-Alder (IEDDA) reaction between tetrazine (Tz) and trans-cyclooctene (TCO) is presented. As proof-of-principle, a TCO-bearing immunoconjugate of the anti-CA19.9 antibody 5B1 and an Al[(18)F]NOTA-labeled tetrazine radioligand were harnessed for the visualization of CA19.9-expressing...

An efficient and bench-stable reagent was synthesized for direct and covalent introduction of tetrazines onto target protein or virus surfaces, which can be further modified based on tetrazine-ene ligation to achieve fluorescence labelling or PEGylation under mild conditions.

There is a great demand for the reliable and quantitative detection of NO2 to monitor control environmental pollution subsequently prevent harmful human health effects. Metal oxide-based chemiresistive sensors detect this notorious gas, but high operating temperatures (100–500 °C) limit their applicability. Organic polymers can perform room-temperature sensing, such are rare due lack functional...