Stereoselective ketone reduction by a carbonyl reductase from Sporobolomyces salmonicolor. Substrate specificity, enantioselectivity and enzyme-substrate docking studies was written by Zhu, Dunming;Yang, Yan;Buynak, John D.;Hua, Ling. And the article was included in Organic & Biomolecular Chemistry in 2006.Computed Properties of C8H9ClO This article mentions the following:
In our effort to search for effective carbonyl reductases, the activity and enantioselectivity of a carbonyl reductase from Sporobolomyces salmonicolor have been evaluated toward the reduction of a variety of ketones. This carbonyl reductase (SSCR) reduces a broad spectrum of ketones including aliphatic and aromatic ketones, as well as α- and β-ketoesters. Among these substrates, SSCR shows highest activity for the reduction of α-ketoesters. Aromatic α-ketoesters are reduced to (S)-α-hydroxy esters, while (R)-enantiomers are obtained from the reduction of aliphatic counterparts. This interesting observation is consistent with enzyme-substrate docking studies, which show that hydride transfer occurs at the different faces of carbonyl group for aromatic and aliphatic α-ketoesters. It is worthy to note that sterically bulky ketone substrates, such as 2′-methoxyacetophenone, 1-adamantyl Me ketone, Et 4,4-dimethyl-3-oxopentanoate and Et 3,3-dimethyl-2-oxobutanoate, are reduced to the corresponding alcs. with excellent optical purity. Thus, SSCR possesses an unusually broad substrate specificity and is especially useful for the reduction of ketones with sterically bulky substituents. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Computed Properties of C8H9ClO).
(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Computed Properties of C8H9ClO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts