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Total Synthesis and Functional Characterization of Selenoneine.

  • Lim D Department for Chemistry, University of Basel, Mattenstrasse 24a, 4002, Basel, Switzerland.
  • Gründemann D Department of Pharmacology, University of Cologne, Faculty of Medicine and University Hospital Cologne, Gleueler Straße 24, 50931, Cologne, Germany.
  • Seebeck FP Department for Chemistry, University of Basel, Mattenstrasse 24a, 4002, Basel, Switzerland.
  • 2019-08-23
Published in:
  • Angewandte Chemie (International ed. in English). - 2019
2-selenoimidazole
antioxidant
natural product
organoselenide
Antioxidants
Ergothioneine
HEK293 Cells
Histidine
Humans
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Organoselenium Compounds
Oxidation-Reduction
English The N-α-trimethyl 2-selenohistidine selenoneine is the selenium isolog of the natural antioxidant ergothioneine. Sulfur-to-selenium substitutions are known to endow proteins and nucleic acids with special activities. In contrast, secondary metabolites that exploit selenium-specific chemistry are rare. Selenoneine therefore provides a unique opportunity to study how natural organoselenides interact with cellular processes. In this report we describe the chemical synthesis of selenoneine and other 2-selenoimidazoles. With synthetic selenoneine at hand we discovered a set of reactivities that distinguish selenoneine from ergothioneine, showing that the two compounds can fill distinct functional niches. Synthetic access to 2-selenoimidazoles should pave the way to explore the pharmaceutical potential and physiological function of this heretofore inaccessible class of compounds.
Language
  • English
Open access status
green
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Persistent URL
https://folia.unifr.ch/global/documents/5498
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