Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans

Richter N, Gröger H, Hummel W (2011)
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY 89(1): 79-89.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Richter, Nina; Gröger, HaraldUniBi; Hummel, WernerUniBi
Einrichtung
Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie
Abstract / Bemerkung
A recombinant enoate reductase from Gluconobacter oxydans was heterologously expressed, purified, characterised and applied in the asymmetric reduction of activated alkenes. In addition to the determination of the kinetic properties, the major focus of this work was to utilise the enzyme in the biotransformation of different interesting compounds such as 3,5,5-trimethyl-2-cyclohexen-1,4-dione (ketoisophorone) and (E/Z)-3,7-dimethyl-2,6-octadienal (citral). The reaction proceeded with excellent stereoselectivities (>99% ee) as well as absolute chemo-and regioselectivity, only the activated C-C bond of citral was reduced by the enoate reductase, while non-activated C-C bond and carbonyl moiety remained untouched. The described strategy can be used for the production of enantiomerically pure building blocks, which are difficult to prepare by chemical means. In general, the results show that the investigated enoate reductase is a promising catalyst for the use in asymmetric C-C bond reductions.
Erscheinungsjahr
2011
Zeitschriftentitel
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
Band
89
Ausgabe
1
Seite(n)
79-89
ISSN
0175-7598
eISSN
1432-0614
Page URI
https://pub.uni-bielefeld.de/record/2344730

Zitieren

Richter N, Gröger H, Hummel W. Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY. 2011;89(1):79-89.
Richter, N., Gröger, H., & Hummel, W. (2011). Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 89(1), 79-89. https://doi.org/10.1007/s00253-010-2793-y
Richter, Nina, Gröger, Harald, and Hummel, Werner. 2011. “Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans”. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY 89 (1): 79-89.
Richter, N., Gröger, H., and Hummel, W. (2011). Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY 89, 79-89.
Richter, N., Gröger, H., & Hummel, W., 2011. Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 89(1), p 79-89.
N. Richter, H. Gröger, and W. Hummel, “Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans”, APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, vol. 89, 2011, pp. 79-89.
Richter, N., Gröger, H., Hummel, W.: Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY. 89, 79-89 (2011).
Richter, Nina, Gröger, Harald, and Hummel, Werner. “Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans”. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY 89.1 (2011): 79-89.

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