Tetrahydrofuran (THF) is one of the most polar ethers and is a widely used solvent for polar reagents. Since THF is very soluble in water and has a relatively low boiling point, signficant amounts are often released into the environment, causing contamination problems. Tetrahydrofuran is not considered to be readily degradable, and concerns of environmental contamination have been raised.
Bernhardt and Diekmann (1991) performed studied the pathway for tetrahydrofuran degradation by Rhodococcus ruber DSM 44190. The pathway shown below is hypothetical. Not all intermediates (e.g. 2-hydroxytetrahydrofuran) were detected. In fact, the isomerization of 2-hydroxytetrahydrofuran might occur spontaneously and not require an enzyme. However, degradation experiments using the same organism were performed with a similar compound, 2,5-dimethyltetrahydrofuran (Bock, C., Kroppenstedt, R.M., and Diekmann, H., 1996, Appl Microbiol Biotechnol. 45:408-410), and those data support the proposed tetrahydrofuran pathway. Thiemer et al. (2003) characterized the pathway in Pseudonocardia sp. strain K1. This strain only uses the left pathway branch.
The following is a text-format tetrahydrofuran pathway map. An organism which can initiate the pathway is given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (16K) format.
Tetrahydrofuran Rhodococcus opacus Pseudonocardia sp. strain K1 | | tetrahydrofuran | hydroxylase | v 2-Hydroxytetrahydrofuran / (only Rhodococcus) 2-hydroxy- / \ 2-hydroxy- tetrahydrofuran / \ tetrahydrofuran dehydrogenase / \ isomerase v v Butyrolactone + 4-Hydroxybutaraldehyde \ / butyrolactone \ / 4-hydroxy- hydrolase \ / butaraldehyde \ / dehydrogenase v v 4-Hydroxybutanoate | | | v Intermediary Metabolism (KEGG)
Page Author(s): Jodi Bjerke
© 2018, EAWAG. All rights reserved. http://eawag-bbd.ethz.ch/thf/thf_map.html