Reaction: isoeugenol + O2 = vanillin + acetaldehyde
For diagram of reaction click here.
Glossary: isoeugenol = 2-methoxy-4-(prop-1-en-1-yl)phenol
Other name(s): iem (gene name)
Systematic name: isoeugenol:oxygen 7,8-oxidoreductase (bond-cleaving)
Comments: Contains Firon(II). The enzyme, charcterised from the bacteria Pseudomonas putida and Pseudomonas nitroreducens, catalyses the epoxidation of the double bond in the side chain of isoeugenol, followed by a second oxygenation and cleavage of the side chain in the form of acetaldehyde.
Links to other databases: BRENDA, EXPASY, ExplorEnz, KEGG, MetaCyc, CAS registry number:
References:
1. Shimoni, E., Ravid, U. and Shoham, Y. Isolation of a Bacillus sp. capable of transforming isoeugenol to vanillin. J. Biotechnol. 78 (2000) 1-9. [PMID: 10702906]
2. Yamada, M., Okada, Y., Yoshida, T. and Nagasawa, T. Biotransformation of isoeugenol to vanillin by Pseudomonas putida IE27 cells. Appl. Microbiol. Biotechnol. 73 (2007) 1025-1030. [PMID: 16944125]
3. Yamada, M., Okada, Y., Yoshida, T. and Nagasawa, T. Purification, characterization and gene cloning of isoeugenol-degrading enzyme from Pseudomonas putida IE27. Arch. Microbiol. 187 (2007) 511-517. [PMID: 17516050]
4. Ryu, J.Y., Seo, J., Unno, T., Ahn, J.H., Yan, T., Sadowsky, M.J. and Hur, H.G. Isoeugenol monooxygenase and its putative regulatory gene are located in the eugenol metabolic gene cluster in Pseudomonas nitroreducens Jin1. Arch. Microbiol. 192 (2010) 201-209. [PMID: 20091296]
5. Ryu, J.Y., Seo, J., Park, S., Ahn, J.H., Chong, Y., Sadowsky, M.J. and Hur, H.G. Characterization of an isoeugenol monooxygenase (iem) from Pseudomonas nitroreducens Jin1 that transforms isoeugenol to vanillin. Biosci. Biotechnol. Biochem. 77 (2013) 289-294. [PMID: 23391906]