Chemistry:Thioselenide

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Dimethyl thioselenide, a simple thioselenide found in some species of Allium[1]

A thioselenide is any organic chemical compound containing a selenium-sulfur bond.

Thioselenides are rare in nature, but have been identified, for example, in some species of Allium[1] and in roasted coffee.[2] The mammalian version of the protein thioredoxin reductase contains a selenocysteine residue which forms a thioselenide (analogous to a disulfide) upon oxidation.[3]

The selenium-sulfur bond length is about 220 picometers.

References

  1. 1.0 1.1 Cai, Xiao-Jia; Uden, Peter C.; Block, Eric; Zhang, Xing; Quimby, Bruce D.; Sullivan, James J. (1994). "Allium chemistry: Identification of natural abundance organoselenium volatiles from garlic, elephant garlic, onion, and Chinese chive using headspace gas chromatography with atomic emission detection". Journal of Agricultural and Food Chemistry 42 (10): 2081–2084. doi:10.1021/jf00046a002. 
  2. Meija, Juris; Bryson, Joshua M.; Vonderheide, Anne P.; Montes-Bayón, Maria; Caruso, Joseph A. (2003). "Studies of Selenium-Containing Volatiles in Roasted Coffee". Journal of Agricultural and Food Chemistry 51 (17): 5116–5122. doi:10.1021/jf034210h. PMID 12903978. 
  3. Lee, S.-R.; Bar-Noy, S.; Kwon, J.; Levine, R. L.; Stadtman, T. C.; Rhee, S. G. (2000). "Mammalian thioredoxin reductase: Oxidation of the C-terminal cysteine/Selenocysteine active site forms a thioselenide, and replacement of selenium with sulfur markedly reduces catalytic activity". Proceedings of the National Academy of Sciences 97 (6): 2521–2526. doi:10.1073/pnas.050579797. PMID 10688911. Bibcode2000PNAS...97.2521L.