Featured Research

from universities, journals, and other organizations

70-year-old chemical mystery solved: How tropolone are synthesized in fungi

Date:
April 16, 2012
Source:
University of Bristol
Summary:
Chemists and biologists have finally cracked one of the longest standing chemical mysteries. They have demonstrated exactly how an unusual class of compounds known as tropolones are synthesized in fungi.

Ring expansion of 3-methylorcinaldehyde to give the tropolone ring.
Credit: Image by R.J. Cox and A.M. Bailey

Chemists and biologists from the University of Bristol have finally cracked one of the longest standing chemical mysteries. In a paper published April 16 in Proceedings 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.

Using a combination of genetic and chemical methods, Dr Andy Bailey and Professor Russell Cox and colleagues were able to identify the genes responsible for this process, blocking the synthetic pathway at different steps and thus demonstrating how, on a molecular scale, the tropolone structure is produced. This is the core of a number of fungal compounds including stipitatic acid, the xenovulenes which are antidepressants and the antimalarial compound puberulic acid.

Knowledge of tropolone biosynthetic pathway is in itself very interesting to chemists, but it may also lead to the discovery of new drugs.

Professor Cox of Bristol's School of Chemistry, who led the project, said: "Members of this class of compound are well known as having antibacterial properties and some have promise as antimalarial treatments -- we now plan to engineer fungi to produce these new compounds."

It is hoped that identification of the enzymes responsible for tropolone synthesis will help in generating a wider range of compounds for evaluation.


Story Source:

The above story is based on materials provided by University of Bristol. Note: Materials may be edited for content and length.


Journal Reference:

  1. J. Davison, A. al Fahad, M. Cai, Z. Song, S. Y. Yehia, C. M. Lazarus, A. M. Bailey, T. J. Simpson, R. J. Cox. Genetic, molecular, and biochemical basis of fungal tropolone biosynthesis. Proceedings of the National Academy of Sciences, 2012; DOI: 10.1073/pnas.1201469109

Cite This Page:

University of Bristol. "70-year-old chemical mystery solved: How tropolone are synthesized in fungi." ScienceDaily. ScienceDaily, 16 April 2012. <www.sciencedaily.com/releases/2012/04/120416154414.htm>.
University of Bristol. (2012, April 16). 70-year-old chemical mystery solved: How tropolone are synthesized in fungi. ScienceDaily. Retrieved July 31, 2014 from www.sciencedaily.com/releases/2012/04/120416154414.htm
University of Bristol. "70-year-old chemical mystery solved: How tropolone are synthesized in fungi." ScienceDaily. www.sciencedaily.com/releases/2012/04/120416154414.htm (accessed July 31, 2014).

Share This




More Matter & Energy News

Thursday, July 31, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Britain Testing Driverless Cars on Roadways

Britain Testing Driverless Cars on Roadways

AP (July 30, 2014) British officials said on Wednesday that driverless cars will be tested on roads in as many as three cities in a trial program set to begin in January. Officials said the tests will last up to three years. (July 30) Video provided by AP
Powered by NewsLook.com
Amid Drought, UCLA Sees Only Water

Amid Drought, UCLA Sees Only Water

AP (July 30, 2014) A ruptured 93-year-old water main left the UCLA campus awash in 8 million gallons of water in the middle of California's worst drought in decades. (July 30) Video provided by AP
Powered by NewsLook.com
Smartphone Powered Paper Plane Debuts at Airshow

Smartphone Powered Paper Plane Debuts at Airshow

AP (July 30, 2014) Smartphone powered paper airplane that was popular on crowdfunding website KickStarter makes its debut at Wisconsin airshow (July 30) Video provided by AP
Powered by NewsLook.com
U.K. To Allow Driverless Cars On Public Roads

U.K. To Allow Driverless Cars On Public Roads

Newsy (July 30, 2014) Driverless cars could soon become a staple on U.K. city streets, as they're set to be introduced to a few cities in 2015. Video provided by Newsy
Powered by NewsLook.com

Search ScienceDaily

Number of stories in archives: 140,361

Find with keyword(s):
Enter a keyword or phrase to search ScienceDaily for related topics and research stories.

Save/Print:
Share:

Breaking News:
from the past week

In Other News

... from NewsDaily.com

Science News

Health News

    Environment News

    Technology News



      Save/Print:
      Share:

      Free Subscriptions


      Get the latest science news with ScienceDaily's free email newsletters, updated daily and weekly. Or view hourly updated newsfeeds in your RSS reader:

      Get Social & Mobile


      Keep up to date with the latest news from ScienceDaily via social networks and mobile apps:

      Have Feedback?


      Tell us what you think of ScienceDaily -- we welcome both positive and negative comments. Have any problems using the site? Questions?
      Mobile: iPhone Android Web
      Follow: Facebook Twitter Google+
      Subscribe: RSS Feeds Email Newsletters
      Latest Headlines Health & Medicine Mind & Brain Space & Time Matter & Energy Computers & Math Plants & Animals Earth & Climate Fossils & Ruins