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Inverse electron-demand Diels-Alder (iEDDA) bioorthogonal conjugation of half-sandwich transition metallocarbonyl entities to a model protein |
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| Authors: | Daria Jamroz Nathalie Fischer-Durand Marcin Palusiak S?awomir Wojtulewski Szymon Jarzyński Marlena St?pniewska Michèle Salmain Bogna Rudolf |
| Institution: | 1. Department of Organic Chemistry, Faculty of Chemistry, University of Lodz, 91–403 Lodz, Poland;2. Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire (IPCM), 75005 Paris, France;3. Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, 90–236 Lodz, Poland;4. Institute of Chemistry, University of Bialystok, Ciolkowskiego 1 K, 15–245 Bialystok, Poland |
| Abstract: | Novel transition metallocarbonyl complexes carrying a norbornene or an oxanorbornene group were synthesized by 4 + 2] cycloaddition between the organometallic maleimide dienophiles and cyclopentadiene or furan, respectively. The oxanorbornene adduct was obtained as a mixture of endo and exo isomers as confirmed by X-ray diffraction and NMR spectroscopy. The (oxa)norbornene groups further provided convenient chemical reporters to carry out inverse electron demand Diels-Alder (iEDDA) reactions with tetrazine derivatives. Detailed kinetic studies with a model tetrazine revealed that faster rates of reaction were determined with both isomers of the oxanorbornene complex with respect to the norbornene complexes. Eventually, incorporation of metallocarbonyl entities into bovine serum albumin equipped with tetrazine handles was achieved as shown by IR spectroscopy of the protein conjugates. |
| Keywords: | iEDDA norbornene tetrazine metallocarbonyl complex bioconjugation |