Epoxidation of conjugated C=C-bonds and sulfur-oxidation of thioethers mediated by NADH:FMN-dependent oxidoreductases.

Autor: Mueller NJ; Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, Austria., Stueckler C, Hall M, Macheroux P, Faber K
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2009 Mar 21; Vol. 7 (6), pp. 1115-9. Date of Electronic Publication: 2009 Jan 26.
DOI: 10.1039/b819057g
Abstrakt: Three FMN-dependent oxidoreductases, YcnD and YhdA from Bacillus subtilis and Lot6p from Saccharomyces cerevisiae, oxidised alpha,beta-unsaturated carbonyl compounds and a thioether, respectively, to furnish the corresponding racemic epoxides or sulfoxide, respectively. The mechanism of this enzyme-mediated (rather than enzyme-catalysed) oxidation was shown to proceed via the NADH-dependent reduction of O(2), forming H(2)O(2), which acted as oxidant in a spontaneous (non-enzymatic) fashion.
Databáze: MEDLINE