Isoindoline-Based Nitroxides as Bioresistant Spin Labels for Protein Labeling via Cysteines and Alkyne Bearing Noncanonical Amino Acids

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2020
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Electron paramagnetic resonance (EPR) spectroscopy in combination with site-directed spin labeling (SDSL) is a powerful tool in protein structural research. Nitroxides are highly suitable spin labeling reagents, but suffer from limited stability in particular in cellular environment. Here, we present the synthesis of a maleimid- and an azide-modified tetraethyl-shielded isoindoline-based nitroxide (M- and Az-TEIO) for labeling of cysteines or the noncanonical amino acid para -ethynyl-l-phenylalanine ( p ENF). We demonstrate high stability of TEIO  site-specifically attached to the protein thioredoxin (TRX) towards reduction in prokaryotic and eukaryotic environments, and conduct double electron-electron resonance (DEER) measurements. We further generate a rotamer library for the new residue p ENF-Az-TEIO that affords a distance distribution that is in agreement with the measured distribution.

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540 Chemie
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bioresistancy, EPR spectroscopy, macromolecular dynamics, protein conformation analysis, site-directed spin labeling
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ISO 690BRAUN, Theresa S., Pia WIDDER, Uwe OSSWALD, Lina GROSS, Lara WILLIAMS, Moritz J. SCHMIDT, Irina HELMLE, Daniel SUMMERER, Malte DRESCHER, 2020. Isoindoline-Based Nitroxides as Bioresistant Spin Labels for Protein Labeling via Cysteines and Alkyne Bearing Noncanonical Amino Acids. In: ChemBioChem. Wiley. 2020, 21(7), pp. 958-962. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201900537
BibTex
@article{Braun2020-04Isoin-47475,
  year={2020},
  doi={10.1002/cbic.201900537},
  title={Isoindoline-Based Nitroxides as Bioresistant Spin Labels for Protein Labeling via Cysteines and Alkyne Bearing Noncanonical Amino Acids},
  number={7},
  volume={21},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={958--962},
  author={Braun, Theresa S. and Widder, Pia and Osswald, Uwe and Groß, Lina and Williams, Lara and Schmidt, Moritz J. and Helmle, Irina and Summerer, Daniel and Drescher, Malte}
}
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