4.6 Article

Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 11, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103925

Keywords

alpha-ketoamides; alkynes; photo-affinity labeling; spin density; thiophenes

Funding

  1. PRIME from the Japan Agency for Medical Research and Development, AMED
  2. Platform Project for Supporting Drug Discovery and Life Science Research (BINDS) from the Japan Agency for Medical Research and Development, AMED
  3. JSPS KAKENHI [21K19053, 21H02070, 20K15957]
  4. Sumitomo Foundation
  5. Grants-in-Aid for Scientific Research [21K19053, 20K15957, 21H02070] Funding Source: KAKEN

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Minimalist photo-reactive probes, consisting of a photo-reactive group and a tag for detection of target proteins, are valuable tools in chemical biology. In this study, minimalist probes based on a 2-thienyl-substituted alpha-ketoamide with an alkyne group on the thiophene ring were developed. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.
Minimalist photo-reactive probes, which consist of a photo-reactive group and a tag for detection of target proteins, are useful tools in chemical biology. Although several diazirine-based and aryl azide-based minimalist probes are available, no keto-based minimalist probe has yet been reported. Here we describe minimalist probes based on a 2-thienyl-substituted alpha-ketoamide bearing an alkyne group on the thiophene ring. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.

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