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Recent Advances in ω-Transaminase-Mediated Biocatalysis for the Enantioselective Synthesis of Chiral Amines
Open AccessFeature PaperArticle

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

Politecnico di Milano, Dipartimento di Chimica, Materiali e Ingegneria Chimica, Via Mancinelli 7, Milano I-20131, Italy
Istituto di Chimica del Riconoscimento Molecolare–CNR, Via Mancinelli 7, Milano I-20131, Italy
Author to whom correspondence should be addressed.
With the exception of the first author, the others are listed in alphabetical order.
Catalysts 2018, 8(8), 308;
Received: 12 July 2018 / Revised: 24 July 2018 / Accepted: 25 July 2018 / Published: 29 July 2018
(This article belongs to the Special Issue Enzyme-Mediated Stereoselective Synthesis)
Chiral β-nitroalcohols are important building blocks in organic chemistry. The synthetic approach that is based on the enzyme-mediated reduction of α-nitroketones has been scarcely considered. In this work, the use of commercial alcohol dehydrogenases (ADHs) for the reduction of aromatic and aliphatic nitroketones is investigated. High conversions and enantioselectivities can be achieved with two specific ADHs, affording either the (S) or (R)-enantiomer of the corresponding nitroalcohols. The reaction conditions are carefully tuned to preserve the stability of the reduced product, and to avoid the hydrolytic degradation of the starting substrate. The further manipulation of the enantioenriched nitroalcohols into Boc-protected amminoalcohols is also described. View Full-Text
Keywords: nitroketone; reduction; alcohol-dehydrogenase; enantioselectivity nitroketone; reduction; alcohol-dehydrogenase; enantioselectivity
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MDPI and ACS Style

Tentori, F.; Brenna, E.; Colombo, D.; Crotti, M.; Gatti, F.G.; Ghezzi, M.C.; Pedrocchi-Fantoni, G. Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones. Catalysts 2018, 8, 308.

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