L. Hunag, E. Romero, A. Ressmann, F. Rudroff, F. Hollmann, M.W. Fraaije, S. Kara:
"Nicotinamide adenine dinucleotide-dependent redox-neutral convergent cascade for lactonizations with Type II flavin-containing monooxygenase";
Advanced Synthesis & Catalysis,
A nicotinamide adenine dinucleotide (NADH)-dependent redox-neutral convergent cascade composed of a recently discovered type II flavin-containing monooxygenase (FMO−E) and horse liver alcohol dehydrogenase (HLADH) has been established. Two model reaction cascades were analyzed for the synthesis of γ-butyrolactone and chiral bicyclic lactones. In the former cascade, all substrates were converted into one single product γ-butyrolactone with high atom efficiency. More than 130 mM γ-butyrolactone were obtained when applying 100 mM cyclobutanone and 50 mM 1,4-butanediol in this cascade. In the second cascade where bicyclo[4.2.0]octan-7-one and cis-1,2-cyclohexanedimethanol were coupled, the ketone substrate was converted to the corresponding normal lactone with an ee value of 89-74% (3aS, 7aS) by FMO−E alone and the abnormal lactone with an ee value of >99% (3aR, 7aS) was formed by both HLADH and FMO−E.
Baeyer-Villiger Monooxygenase; Re-dox-neutral Cascade; Cofactor Specificity; AlcoholDehydrogenase; Biocatalysis
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