Sunday, 22 April 2012

70-Year-Old Chemical Mystery Solved: How Tropolone Are Synthesized in Fungi

Chemists and biologists from the University of Bristol have finally cracked one of the longest standing chemical mysteries. In a paper published April 16 inProceedings of the National Academy of Sciences, the team demonstrate exactly how an unusual class of compounds known as tropolones are synthesised in fungi.

In 1942, an 'unidentifiable' aromatic compound known as stipitatic acid was first isolated from fungi. By 1945 the structure was solved but it was so unique that it caused a revolution in the understanding of organic chemistry.
Stipitatic acid is very unusual as it displays similar aromatic properties to the six-membered rings in benzene-based compounds, but is a seven-membered carbon ring known as a tropolone. New theoretical models developed to understand tropolones now underpin our understanding of structure and bonding in organic chemistry.
However it remained a mystery as to how fungi are able to synthesise such a product under biological conditions -- until now. Read more

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