Search results for "Inverse electron-demand Diels–Alder reaction"
showing 5 items of 5 documents
Approach Matters : The Kinetics of Interfacial Inverse-Electron Demand Diels-Alder Reactions
2017
Rapid and quantitative click functionalization of surfaces remains an interesting challenge in surface chemistry. In this regard, inverse electron demand Diels Alder (IEDDA) reactions represent a promising metal-free candidate. Herein, we reveal quantitative surface functionalization within 15 min. Furthermore, we report the comprehensive effects of substrate stereochemistry, surrounding microenvironment and substrate order on the reaction kinetics as obtained via a combination of XPS and surface-bound mass spectrometry (DART-MS).
Modular Assembly of Multimodal Imaging Agents through an Inverse Electron Demand Diels–Alder Reaction
2019
International audience; The combination of two imaging probes on a same biomolecule gives access to targeted bimodal imaging agents that can provide more accurate diagnosis, complementary information, or that may be used in different applications, such as PET imaging and fluorescence imagingassisted surgery. In this study, we demonstrate that dichlorotetrazine, a small, commercially available compound, can be used as a modular platform to easily assemble various imaging probes. Doubly-labeled tetrazines can then be conjugated to a protein through a biorthogonal IEDDA reaction. A series of difunctionalized tetrazine compounds containing various chelating agents and fluorescent dyes was synth…
Influence of Reactant Polarity on the Course of the Inverse-Electron-Demand Diels−Alder Reaction. A DFT Study of Regio- and Stereoselectivity, Presen…
1999
The molecular mechanisms for the inverse-electron-demand Diels−Alder reactions between nitroethene and three substituted ethenes (propene, methyl vinyl ether, and dimethylvinylamine) to give the corresponding nitroso cycloadducts have been characterized with density functional theory methods using the B3LYP/6-31G* calculational level. On the basis of stability arguments and molecular orbital analysis relative rates, regioselectivity, and stereoselectivity, the presence of Lewis acid catalyst modeled by the BH3 system and the inclusion of solvent effects as a function of the nature of substituent in the dienophile fragment are analyzed and discussed. The ortho attack mode presents transition…
ChemInform Abstract: Influence of Reactant Polarity on the Course of the Inverse-Electron-Demand Diels-Alder Reaction. A DFT Study of Regio- and Ster…
2010
The molecular mechanisms for the inverse-electron-demand Diels−Alder reactions between nitroethene and three substituted ethenes (propene, methyl vinyl ether, and dimethylvinylamine) to give the corresponding nitroso cycloadducts have been characterized with density functional theory methods using the B3LYP/6-31G* calculational level. On the basis of stability arguments and molecular orbital analysis relative rates, regioselectivity, and stereoselectivity, the presence of Lewis acid catalyst modeled by the BH3 system and the inclusion of solvent effects as a function of the nature of substituent in the dienophile fragment are analyzed and discussed. The ortho attack mode presents transition…
Evaluation of the inverse electron demand Diels-Alder reaction in rats using a scandium-44-labelled tetrazine for pretargeted PET imaging
2019
Background Pretargeted imaging allows the use of short-lived radionuclides when imaging the accumulation of slow clearing targeting agents such as antibodies. The biotin-(strept)avidin and the bispecific antibody-hapten interactions have been applied in clinical pretargeting studies; unfortunately, these systems led to immunogenic responses in patients. The inverse electron demand Diels-Alder (IEDDA) reaction between a radiolabelled tetrazine (Tz) and a trans-cyclooctene (TCO)-functionalized targeting vector is a promising alternative for clinical pretargeted imaging due to its fast reaction kinetics. This strategy was first applied in nuclear medicine using an 111In-labelled Tz to image TC…