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Nitroxides are highly suitable spin labeling reagents, but suffer from limited stability, particularly in the cellular environment. Herein we present the synthesis of a maleimide\u2010 and an azide\u2010modified tetraethyl\u2010shielded isoindoline\u2010based nitroxide (M\u2010 and Az\u2010TEIO) for labeling of cysteines or the noncanonical amino acid <jats:italic>para<\/jats:italic>\u2010ethynyl\u2010<jats:sc>l<\/jats:sc>\u2010phenylalanine (<jats:italic>p<\/jats:italic>ENF). We demonstrate the high stability of TEIO site\u2010specifically attached to the protein thioredoxin (TRX) against reduction in prokaryotic and eukaryotic environments, and conduct double electron\u2013electron resonance (DEER) measurements. We further generate a rotamer library for the new residue <jats:italic>p<\/jats:italic>ENF\u2010Az\u2010TEIO that affords a distance distribution that is in agreement with the measured distribution.<\/jats:p>","DOI":"10.1002\/cbic.201900537","type":"journal-article","created":{"date-parts":[[2019,10,28]],"date-time":"2019-10-28T03:15:01Z","timestamp":1572232501000},"page":"958-962","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Isoindoline\u2010Based Nitroxides as Bioresistant Spin Labels for Protein Labeling through Cysteines and Alkyne\u2010Bearing Noncanonical Amino Acids"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2065-5840","authenticated-orcid":false,"given":"Theresa Sophie","family":"Braun","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"},{"name":"Konstanz Research School Chemical Biology (KoRS-CB) University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5068-2658","authenticated-orcid":false,"given":"Pia","family":"Widder","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"},{"name":"Konstanz Research School Chemical Biology (KoRS-CB) University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Uwe","family":"Osswald","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0489-6193","authenticated-orcid":false,"given":"Lina","family":"Gro\u00df","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6879-938X","authenticated-orcid":false,"given":"Lara","family":"Williams","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1933-1999","authenticated-orcid":false,"given":"Moritz","family":"Schmidt","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina","family":"Helmle","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"},{"name":"Present address: Faculty of Science Department of Pharmaceutical Biology University of T\u00fcbingen  Auf der Morgenstelle 8 72076 T\u00fcbingen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3019-7241","authenticated-orcid":false,"given":"Daniel","family":"Summerer","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Chemical Biology TU Dortmund  Otto-Hahn-Strasse 4a 44227 Dortmund Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3571-3452","authenticated-orcid":false,"given":"Malte","family":"Drescher","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"},{"name":"Konstanz Research School Chemical Biology (KoRS-CB) University of Konstanz  Universit\u00e4tsstrasse 10 78457 Konstanz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,12,6]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmre.1999.1944"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-physchem-032511-143716"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/prot.340060312"},{"key":"e_1_2_2_4_1","author":"Bonucci A.","year":"2019","journal-title":"ChemBioChem"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp401806g"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201900341"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710184"},{"key":"e_1_2_2_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201710184"},{"key":"e_1_2_2_9_2","first-page":"999","volume":"49","author":"Gophane D. 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