Question

The anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without metabolism, inhibition occurs by reaction of orlistat with a serine residue of the enzyme, forming a covalently bound, inactive enzyme product. Draw the structure of the product formed during inhibition.

Short answer

Orlistat is acquired from lipstatin and is employed to cure obesity. It has several side effects that are connected with gastro-intestinal problems. Food comprising excessive fat content can be avoided to prevent them.

Step-by-step solution

Orlistat

Orlistat is acquired from lipstatin and is employed to cure obesity. It has several side effects that are connected with gastro-intestinal problems. Food comprising excessive fat content can be avoided to prevent them.

Enzyme inhibitor

Enzyme inhibitor constitutes a molecule that connects to an enzyme and lessens its activity. All the molecules connecting with enzymes are not inhibitors. The enzymatic activity elevates due to the linking of the enzyme activator with the enzyme.

Structure of the product formed during the inhibition

The given drug comprises a beta lactone ring which can be opened by the inhibitors. The structure of the compound can be given as:

The attack of the hydroxyl group on the beta-lactone ring leads to inhibition producing an inactive enzyme. The chemical reaction can be given as: