Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Steric vs. electronic effects in the Lactobacillus brevis ADH-catalyzed bioreduction of ketones.Application of 17190-29-3.
Lactobacillus brevis ADH (LBADH) is an alc. dehydrogenase that is commonly employed to reduce alkyl or aryl ketones usually bearing a Me, an Et or a chloromethyl as a small ketone substituent to the corresponding (R)-alcs. Herein we have tested a series of 24 acetophenone derivatives differing in their size and electronic properties for their reduction employing LBADH. After plotting the relative activity against the measured substrate volumes we observed that apart from the substrate size other effects must be responsible for the activity obtained. Compared to acetophenone (100% relative activity), other small substrates such as propiophenone, α,α,α-trifluoroacetophenone, α-hydroxyacetophenone, and benzoylacetonitrile had relative activities lower than 30%, while medium-sized ketones such as α-bromo-, α,α-dichloro-, and α,α-dibromoacetophenone presented relative activities between 70% and 550%. Moreover, the comparison between the enzymic activity and the obtained final conversions using an excess or just 2.5 equivalent of the hydrogen donor 2-propanol, denoted again deviations between them. These data supported that these hydrogen transfer (HT) transformations are mainly thermodynamically controlled. For instance, bulky α-halogenated derivatives could be quant. reduced by LBADH even employing 2.5 equivalent of 2-propanol independently of their kinetic values. Finally, we found good correlations between the IR absorption band of the carbonyl groups and the degrees of conversion obtained in these HT processes, making this simple method a convenient tool to predict the success of these transformations.
In some applications, this compound(17190-29-3)Application of 17190-29-3 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics