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Nanomaterials 2018, 8(10), 853; https://doi.org/10.3390/nano8100853

Stereoselective Double Reduction of 3-Methyl-2-cyclohexenone, by Use of Palladium and Platinum Nanoparticles, in Tandem with Alcohol Dehydrogenase

1
Department of Engineering and Geology (INGEO), G. d’Annunzio University of Chieti-Pescara, Viale Pindaro 42, I-66100 Chieti Scalo, Italy
2
Department of Biotechnology, Delft University of Technology, van der Maasweg 9, 2629HZ Delft, The Netherlands
3
Department of Philosophical, Educational and Economic Sciences, G. d’Annunzio University of Chieti-Pescara, Via dei Vestini 31, I-66100 Chieti Scalo, Italy
4
Department of Pharmacy, G. d’Annunzio University of Chieti-Pescara, Via dei Vestini 31, I-66100 Chieti Scalo, Italy
5
Department of Chemistry, University of Firenze, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy
*
Author to whom correspondence should be addressed.
Received: 21 September 2018 / Revised: 12 October 2018 / Accepted: 17 October 2018 / Published: 19 October 2018
(This article belongs to the Special Issue Nanomaterials in Biocatalyst)
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Abstract

The combination of metal nanoparticles (Pd or Pt NPs) with NAD-dependent thermostable alcohol dehydrogenase (TADH) resulted in the one-flask catalytic double reduction of 3-methyl-2-cyclohexenone to 3-(1S,3S)-methylcyclohexanol. In this article, some assumptions about the interactions between a chemocatalyst and a biocatalyst have been proposed. It was demonstrated that the size of the NPs was the critical parameter for the mutual inhibition: the bigger the NPs, the more harmful for the enzyme they were, even if the NPs themselves were only moderately inactivated. Conversely, the smaller the NPs, the more minimal the TADH denaturation, although they were dramatically inhibited. Resuming, the chemocatalysts were very sensitive to deactivation, which was not related to the amount of enzyme used, while the inhibition of the biocatalyst can be strongly reduced by minimizing the NPs/TADH ratio used to catalyze the reaction. Among some methods to avoid direct binding of NPs with TADH, we found that using large Pd NPs and protecting their surfaces with a silica shell, the overall yield of 3-(1S,3S)-methylcyclohexanol was maximized (36%). View Full-Text
Keywords: nanoparticles; biocatalysis; palladium; platinum; chemoenzymatic catalysis; alcohol dehydrogenase; tandem reaction; nanocatalysis nanoparticles; biocatalysis; palladium; platinum; chemoenzymatic catalysis; alcohol dehydrogenase; tandem reaction; nanocatalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Coccia, F.; Tonucci, L.; Del Boccio, P.; Caporali, S.; Hollmann, F.; D’Alessandro, N. Stereoselective Double Reduction of 3-Methyl-2-cyclohexenone, by Use of Palladium and Platinum Nanoparticles, in Tandem with Alcohol Dehydrogenase. Nanomaterials 2018, 8, 853.

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