Chapter 8: Problem 2

Why do the two enantiomers of glutethimide (8.41) undergo P450-catalyzed hydroxylation at two different sites?

Short Answer

Expert verified

Due to the different spatial orientations of the two enantiomers of glutethimide, they interact differently with the P450 enzyme, resulting in the hydroxylation occurring at different sites in each of these enantiomers.

Step by step solution

Understanding Enantiomers

Enantiomers are pairs of molecules that are non-superimposable mirror images of each other. They have the same molecular formula and sequence of bonded atoms, but differ in the three-dimensional orientations of their atoms in space. In the case of glutethimide, this means that even though they have the same chemical structure, the spatial arrangement of atoms is different and this makes its two enantiomers chemically unique.

Understanding P450-catalyzed Hydroxylation

Cytochrome P450 enzymes are responsible for catalyzing the hydroxylation of organic substances. They act by inserting one atom of oxygen into the alkyl group resulting in the formation of alcohols. Since these enzymes have a complex three-dimensional shape, their interaction with the substrates is strongly dependent on the spatial configuration of the substrate.

Different Hydroxylation Sites of the two Glutethimide Enantiomers

As the two forms of glutethimide are mirror images of each other, they exhibit different spatial orientations. Hence, the P450 enzymes will interact differently with each of them. Due to the difference in the spatial arrangement of atoms, the P450 enzyme will recognize each enantiomer differently and lead to the hydroxylation occurring at different locations within the molecules.

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Why do the two enantiomers of glutethimide (8.41) undergo P450-catalyzed hydroxylation at two different sites?

Short Answer

Step by step solution

Understanding Enantiomers

Understanding P450-catalyzed Hydroxylation

Different Hydroxylation Sites of the two Glutethimide Enantiomers

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