Pyrone

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Pyrones or pyranones are a class of heterocyclic chemical compounds. They contain an unsaturated six-membered ring containing one oxygen atom and a ketone functional group.[1] There are two isomers denoted as 2-pyrone and 4-pyrone. The 2-pyrone (or α-pyrone) structure is found in nature as part of the coumarin ring system. 4-Pyrone (or γ-pyrone) is found in some natural chemical compounds such as chromone, maltol and kojic acid.

In July 2013, α-pyrones were identified as a new class of signalling molecule in bacterial communication, similar to quorum sensing. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce N-acylhomoserine lactone QS signaling molecules) are known as LuxR "solos", to which pyrones bind as ligands facilitating cell-cell communication.[2]

See also

  • Furanone, which has one fewer carbon atom in the ring.

References

  1. ^ Streitwieser, Jr., Andrew; Heathcock, Clayton H. (1985). Introduction to Organic Chemistry (Third ed.). pp. 1038–1040. ISBN 978-0-02-418140-4.
  2. ^ Brachmann, Alexander; Brameyer, S.; Kresovic, D.; Hitkova, I.; Kopp, Y.; Manske, C.; Schubert, K.; Bode, H. B.; Heermann, R. (14 July 2013). "Pyrones as bacterial signaling molecules". Nature Chemical Biology. Nature Publishing Group. 9 (9): 573–578. doi:10.1038/nchembio.1295. PMID 23851573.


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