Asymmetric Biocatalytic Reduction of Ketones

Gröger H, Hummel W, Metzner R (2012)
In: Synthetic Methods VI – Enzymatic and Semi-Enzymatic. Carreira EM, Yamamoto H (Eds); Comprehensive Chirality, 7. Oxford: Elsevier: 181-215.

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Carreira, Erick M. ; Yamamoto, Hisashi
Abstract
The use of enzymes as catalysts in enantioselective ketone reduction has gained broad synthetic interest in organic chemistry since this biocatalytic methodology was found to be a versatile, robust, efficient, and industrially feasible synthetic approach toward enantiomerically pure alcohols. In such processes, which are based on the use of isolated enzymes, immobilized enzymes, and recombinant whole-cell catalysts, respectively, different types of cofactor regenerations based in particular on substrate- and enzyme-coupled methods have been successfully applied. The advantages of these types of alcohol dehydrogenase (ADH)-catalyzed ketone reductions are not only the well-known excellent enantio-, diastereo-, and regioselectivities of enzymes but also the high volumetric productivities and excellent substrate loadings that are tolerated by many (recombinant) biocatalyst systems. With respect to the search for suitable ADHs, a broad range of well-established screening tools have been developed. In addition, numerous recombinant ADHs are already available, and the known ADHs show a broad, often complementary substrate spectrum. Furthermore, biocatalytic ketone reductions have also demonstrated their suitability to be combined with other enzymatic or ‘classic’ chemical or chemocatalytic reaction steps toward chemoenzymatic one-pot multistep processes.
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Gröger H, Hummel W, Metzner R. Asymmetric Biocatalytic Reduction of Ketones. In: Carreira EM, Yamamoto H, eds. Synthetic Methods VI – Enzymatic and Semi-Enzymatic. Comprehensive Chirality. Vol 7. Oxford: Elsevier; 2012: 181-215.
Gröger, H., Hummel, W., & Metzner, R. (2012). Asymmetric Biocatalytic Reduction of Ketones. In E. M. Carreira & H. Yamamoto (Eds.), Comprehensive Chirality: Vol. 7. Synthetic Methods VI – Enzymatic and Semi-Enzymatic (pp. 181-215). Oxford: Elsevier.
Gröger, H., Hummel, W., and Metzner, R. (2012). “Asymmetric Biocatalytic Reduction of Ketones” in Synthetic Methods VI – Enzymatic and Semi-Enzymatic, ed. E. M. Carreira and H. Yamamoto Comprehensive Chirality, vol. 7, (Oxford: Elsevier), 181-215.
Gröger, H., Hummel, W., & Metzner, R., 2012. Asymmetric Biocatalytic Reduction of Ketones. In E. M. Carreira & H. Yamamoto, eds. Synthetic Methods VI – Enzymatic and Semi-Enzymatic. Comprehensive Chirality. no.7 Oxford: Elsevier, pp. 181-215.
H. Gröger, W. Hummel, and R. Metzner, “Asymmetric Biocatalytic Reduction of Ketones”, Synthetic Methods VI – Enzymatic and Semi-Enzymatic, E.M. Carreira and H. Yamamoto, eds., Comprehensive Chirality, vol. 7, Oxford: Elsevier, 2012, pp.181-215.
Gröger, H., Hummel, W., Metzner, R.: Asymmetric Biocatalytic Reduction of Ketones. In: Carreira, E.M. and Yamamoto, H. (eds.) Synthetic Methods VI – Enzymatic and Semi-Enzymatic. Comprehensive Chirality. 7, p. 181-215. Elsevier, Oxford (2012).
Gröger, Harald, Hummel, Werner, and Metzner, Richard. “Asymmetric Biocatalytic Reduction of Ketones”. Synthetic Methods VI – Enzymatic and Semi-Enzymatic. Ed. Erick M. Carreira and Hisashi Yamamoto. Oxford: Elsevier, 2012.Vol. 7. Comprehensive Chirality. 181-215.
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