REPRESENTATIVE CARBON COMPOUNDS:
FUNCTIONAL GROUPS, INTERMOLECULAR FORCES,
AND INFRARED (IR) SPECTROSCOPY
Structure Is Everything
- The three-dimensional structure of an organic molecule and the functional groups
it contains determine its biological function.
- Crixivan, a drug produced by Merck and Co. (the world’s premier drug firm, $1
billion annual research spending), is widely used in the fight against AIDS
(acquired immune deficiency syndrome).
N
N OH
NH O
HN
H
H H
O
HO H
C 6 H 5
H
Crixivan (an HIV protease inhibitor)
1) Crixivan inhibits an enzyme called HIV (human immunodeficiency virus)
protease.
2) Using computers and a process of rational chemical design, chemists arrived at a
basic structure that they used as a starting point (lead compound).
3) Many compounds based on this lead are synthesized then until a compound had
optimal potency as a drug has been found.
4) Crixivan interacts in a highly specific way with the three-dimensional structure
of HIV protease.
5) A critical requirement for this interaction is the hydroxyl (OH) group near the
center of Crixivan. This hydroxyl group of Crixivan mimics the true chemical
intermediate that forms when HIV protease performs its task in the AIDS virus.
6) By having a higher affinity for the enzyme than its natural reactant, Crixivan ties
