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

Publikationstyp
Journal Article
Date Issued
2017-06-19
Sprache
English
Author(s)
Huang, Lei  
Romero, Elvira  
Ressmann, Anna K.  
Rudroff, Florian  
Hollmann, Frank  
Fraaije, Marco W.  
Kara, Selin  
Institut
Technische Biokatalyse V-6  
TORE-URI
http://hdl.handle.net/11420/3012
Journal
Advanced synthesis & catalysis  
Volume
359
Issue
12
Start Page
2142
End Page
2148
Citation
Advanced Synthesis and Catalysis 12 (359): 2142-2148 (2017-06-19)
Publisher DOI
10.1002/adsc.201700401
Scopus ID
2-s2.0-85019618467
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.).
DDC Class
000: Allgemeines, Wissenschaft
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