Stereochemistry

The world around us is brimming with asymmetry. From the spiral of a seashell to the curl of a fingerprint, handedness, or chirality, plays a fascinating role in both nature and human invention. In the realms of organic and biochemistry, chirality takes center stage, dramatically influencing the properties and functions of molecules. The proteins in our bodies, which serve as catalysts for countless biochemical reactions, are chiral. This inherent asymmetry demands the precise development of chiral drug entities, as only specific orientations will fit and interact effectively with these biological targets.

Chiral
chi·ral
/ˈkīrəl/
      adjective
      CHEMISTRY
  1. asymmetric in such a way that the structure and its mirror image are not superimposable. Chiral compounds are typically optically active (i.e. they rotate plane polarized light).  Many larger organic molecules often have one or more chiral centers (sometimes called chiral centers or asymmetric centers) where four different groups are attached to a carbon atom.

 

Enalapril, Angiotensin-Converting Enzyme (ACE) inhibitor for hypertension, was introduced in Acids, Bases and Reaction chapter.  Enalapril is a chiral molecule.  In fact, it has three chiral centers.  If any one of these stereocenters were different the drug would not be as effective.  Enalapril must "fit" inside the active site of ACE to be effective.   


ActionEnalapril is shown below.  Can you find 3 carbons in Enalapril that have 4 different groups attached them?
Additional Reading

Chapter 5 McMurry