Details
| Original language | English |
|---|---|
| Pages (from-to) | 2142-2148 |
| Number of pages | 7 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 12 |
| Early online date | 22 May 2017 |
| Publication status | Published - 19 Jun 2017 |
| Externally published | Yes |
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% (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.).
Keywords
- Alcohol Dehydrogenase, Baeyer-Villiger Monooxygenase, Biocatalysis, Cofactor Specificity, Redox-neutral Cascade
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Advanced Synthesis and Catalysis, Vol. 359, No. 12, 19.06.2017, p. 2142-2148.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Nicotinamide Adenine Dinucleotide-Dependent Redox-Neutral Convergent Cascade for Lactonizations with Type II Flavin-Containing Monooxygenase
AU - Huang, Lei
AU - Romero, Elvira
AU - Ressmann, Anna K.
AU - Rudroff, Florian
AU - Hollmann, Frank
AU - Fraaije, Marco W.
AU - Kara, Selin
N1 - Funding Information: S.K. thanks Fonds der Chemischen Industrie (Frankfurt, Germany) for the financial support (Grant No: SK 196/20). L.H. thanks China Scholarship Council (CSC) for the financial support. A.K.R and F.R. thank the FWF (Grant No: P28477-B21), the COST action Systems Biocatalysis WG2 and TU Wien ABC-Top Anschubfinanzierung for financial support. The authors thank Dr. Diederik Johannes Opperman (University of the Free State, South Africa) for the recombinant plasmid containing HLADH gene.
PY - 2017/6/19
Y1 - 2017/6/19
N2 - 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.).
AB - 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.).
KW - Alcohol Dehydrogenase
KW - Baeyer-Villiger Monooxygenase
KW - Biocatalysis
KW - Cofactor Specificity
KW - Redox-neutral Cascade
UR - http://www.scopus.com/inward/record.url?scp=85019618467&partnerID=8YFLogxK
U2 - 10.1002/adsc.201700401
DO - 10.1002/adsc.201700401
M3 - Article
AN - SCOPUS:85019618467
VL - 359
SP - 2142
EP - 2148
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 12
ER -