Nicotinamide Adenine Dinucleotide-Dependent Redox-Neutral Convergent Cascade for Lactonizations with Type II Flavin-Containing Monooxygenase

Nicotinamide Adenine Dinucleotide-Dependent Redox-Neutral Convergent Cascade for Lactonizations with Type II Flavin-Containing Monooxygenase

Huang, Lei (Hamburg University of Technology)
Romero, Elvira (University Medical Center Groningen)
Ressmann, Anna K. (Technische Universität Wien)
Rudroff, Florian (Technische Universität Wien)
Hollmann, F. (TU Delft BT/Biocatalysis)
Fraaije, Marco W. (University Medical Center Groningen)
Kara, S. (Hamburg University of Technology)

2017-06-19

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. (Figure presented.).

Alcohol Dehydrogenase
Baeyer-Villiger Monooxygenase
Biocatalysis
Cofactor Specificity
Redox-neutral Cascade

http://resolver.tudelft.nl/uuid:0537ee23-d7a4-499d-91fc-83094718a284

https://doi.org/10.1002/adsc.201700401

2018-06-19

1615-4150

Advanced Synthesis & Catalysis, 359 (12), 2142-2148

Accepted Author Manuscript

Institutional Repository

journal article

© 2017 Lei Huang, Elvira Romero, Anna K. Ressmann, Florian Rudroff, F. Hollmann, Marco W. Fraaije, S. Kara