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Nicotinamide Adenine Dinucleotide-Dependent Redox-Neutral Convergent Cascade for Lactonizations with Type II Flavin-Containing Monooxygenase.
- Source :
-
Advanced Synthesis & Catalysis . Jun2017, Vol. 359 Issue 12, p2142-2148. 7p. - Publication Year :
- 2017
-
Abstract
- 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% (3a S, 7a S) by FMO−E alone and the abnormal lactone with an ee value of >99% (3a R, 7a S) was formed by both HLADH and FMO−E. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 359
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 123671442
- Full Text :
- https://doi.org/10.1002/adsc.201700401