Single‐Molecule Observation of Intermediates in Bioorthogonal 2‐Cyanobenzothiazole Chemistry

Abstract: We report a single‐molecule mechanistic investigation into 2‐cyanobenzothiazole (CBT) chemistry within a protein nanoreactor. When simple thiols reacted reversibly with CBT, the thioimidate monoadduct was approximately 80‐fold longer‐lived than the tetrahedral bisadduct, with important implications for the design of molecular walkers. Irreversible condensation between CBT derivatives and N‐terminal cysteine residues has been established as a biocompatible reaction for site‐selective biomolecular labeling and imaging. During the reaction between CBT and aminothiols, we resolved two transient intermediates, the thioimidate and the cyclic precursor of the thiazoline product, and determined the rate constants associated with the stepwise condensation, thereby providing critical information for a variety of applications, including the covalent inhibition of protein targets and dynamic combinatorial chemistry.

Angaben zum Objekt

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Single‐Molecule Observation of Intermediates in Bioorthogonal 2‐Cyanobenzothiazole Chemistry ; volume:59 ; number:36 ; year:2020 ; pages:15711-15716 ; extent:6 ; Angewandte Chemie / International edition. International edition ; 59, Heft 36 (2020), 15711-15716 (gesamt 6)

Beteiligte, Orts- und Zeitangaben

• Urheber: Qing, Yujia ; Liu, Mira D. ; Hartmann, Denis ; Zhou, Linna ; Ramsay, William J. ; Bayley, Hagan

Weitere Informationen

• DOI: 10.1002/anie.202005729
• URN: urn:nbn:de:101:1-2022061313123542242990
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Letzte Aktualisierung: 15.08.2025, 07:27 MESZ