Protein Spin Labeling with a Photocaged Nitroxide Using Diels-Alder Chemistry

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2019
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European Union (EU): 772027
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SPICE: Spectroscopy in cells with tailored in-vivo labelling strategies and multiply addressable nano-structural probes
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Chembiochem. 2019, 20(19), pp. 2479-2484. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201900318
Zusammenfassung

EPR spectroscopy of diamagnetic bio-macromolecules is based on site-directed spin labeling (SDSL). Here, we present a novel labeling strategy for proteins. We developed and synthesized a nitroxide-based spin label that can be ligated to proteins by an inverse-electron-demand Diels-Alder (DAinv) cycloaddition to genetically encoded non-canonical amino acids (ncAA). The nitroxide moiety is shielded by a photoremovable protecting group (PPG) with an attached tetraethylene glycol unit to achieve water solubility. We demonstrate SDSL of two model proteins with the PaNDA (Photoactivatable Nitroxide for DAinv reaction) label. Our strategy features high reaction rates combined with high selectivity, and the possibility to deprotect the nitroxide in E. coli lysate.

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540 Chemie
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EPR spectroscopy, Cycloaddition, Bioorthogonal chemistry, non-canonical amino acids, Site-directed spin labeling
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ISO 690KUGELE, Anandi, Bjarne SILKENATH, Jakob LANGER, Valentin WITTMANN, Malte DRESCHER, 2019. Protein Spin Labeling with a Photocaged Nitroxide Using Diels-Alder Chemistry. In: Chembiochem. 2019, 20(19), pp. 2479-2484. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201900318
BibTex
@article{Kugele2019-10Prote-46050,
  year={2019},
  doi={10.1002/cbic.201900318},
  title={Protein Spin Labeling with a Photocaged Nitroxide Using Diels-Alder Chemistry},
  number={19},
  volume={20},
  issn={1439-4227},
  journal={Chembiochem},
  pages={2479--2484},
  author={Kugele, Anandi and Silkenath, Bjarne and Langer, Jakob and Wittmann, Valentin and Drescher, Malte}
}
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