We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Stereoselective Double Reduction of 3-Methyl-2-cyclohexenone, by Use of Palladium and Platinum Nanoparticles, in Tandem with Alcohol Dehydrogenase.
- Authors
Coccia, Francesca; Tonucci, Lucia; Del Boccio, Piero; Caporali, Stefano; Hollmann, Frank; d'Alessandro, Nicola
- 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%).
- Subjects
STEREOSELECTIVE reactions; CYCLOHEXENONES; ALCOHOL dehydrogenase
- Publication
Nanomaterials (2079-4991), 2018, Vol 8, Issue 10, p853
- ISSN
2079-4991
- Publication type
Article
- DOI
10.3390/nano8100853