Double Nitroxide Labeling by Copper-Catalyzed Azide–Alkyne Cycloadditions with Noncanonical Amino Acids for Electron Paramagnetic Resonance Spectroscopy

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dc.contributor.authorWidder, Pia
dc.contributor.authorBerner, Frederic
dc.contributor.authorSummerer, Daniel
dc.contributor.authorDrescher, Malte
dc.date.accessioned2019-06-13T11:27:50Z
dc.date.available2019-06-13T11:27:50Z
dc.date.issued2019-05-17eng
dc.description.abstractElectron paramagnetic resonance spectroscopy in combination with site-directed spin labeling (SDSL) is an important tool to obtain long-range distance restraints for protein structural research. We here study a variety of azide- and alkyne-bearing noncanonical amino acids (ncAA) in terms of protein single- and double-incorporation efficiency via nonsense suppression, metabolic stability, yields of nitroxide labeling via copper-catalyzed [3 + 2] azide–alkyne cycloadditions (CuAAC), and spectroscopic properties in continuous-wave and double electron–electron resonance measurements. We identify para-ethynyl-l-phenylalanine and para-propargyloxy-l-phenylalanine as suitable ncAA for CuAAC-based SDSL that will complement current SDSL approaches, particularly in cases in which essential cysteines of a target protein prevent the use of sulfhydryl-reactive spin labels.eng
dc.description.versionpublishedeng
dc.identifier.doi10.1021/acschembio.8b01111eng
dc.identifier.pmid30998314eng
dc.identifier.ppn1667470981
dc.identifier.urihttps://kops.uni-konstanz.de/handle/123456789/45999
dc.language.isoengeng
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dc.subject.ddc540eng
dc.titleDouble Nitroxide Labeling by Copper-Catalyzed Azide–Alkyne Cycloadditions with Noncanonical Amino Acids for Electron Paramagnetic Resonance Spectroscopyeng
dc.typeJOURNAL_ARTICLEeng
dspace.entity.typePublication
kops.citation.bibtex
@article{Widder2019-05-17Doubl-45999,
  year={2019},
  doi={10.1021/acschembio.8b01111},
  title={Double Nitroxide Labeling by Copper-Catalyzed Azide–Alkyne Cycloadditions with Noncanonical Amino Acids for Electron Paramagnetic Resonance Spectroscopy},
  number={5},
  volume={14},
  issn={1554-8929},
  journal={ACS Chemical Biology},
  pages={839--844},
  author={Widder, Pia and Berner, Frederic and Summerer, Daniel and Drescher, Malte}
}
kops.citation.iso690WIDDER, Pia, Frederic BERNER, Daniel SUMMERER, Malte DRESCHER, 2019. Double Nitroxide Labeling by Copper-Catalyzed Azide–Alkyne Cycloadditions with Noncanonical Amino Acids for Electron Paramagnetic Resonance Spectroscopy. In: ACS Chemical Biology. 2019, 14(5), pp. 839-844. ISSN 1554-8929. eISSN 1554-8937. Available under: doi: 10.1021/acschembio.8b01111deu
kops.citation.iso690WIDDER, Pia, Frederic BERNER, Daniel SUMMERER, Malte DRESCHER, 2019. Double Nitroxide Labeling by Copper-Catalyzed Azide–Alkyne Cycloadditions with Noncanonical Amino Acids for Electron Paramagnetic Resonance Spectroscopy. In: ACS Chemical Biology. 2019, 14(5), pp. 839-844. ISSN 1554-8929. eISSN 1554-8937. Available under: doi: 10.1021/acschembio.8b01111eng
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