Figure 5.7 Only one of the two amino acid enantiomers shown can achieve
three-point binding with the hypothetical binding site (e.g., in an
enzyme).
5.4 HISTORICAL ORIGIN OF STEREOCHEMISTRY
- Stereochemistry: founded by Louis Pasteur in 1848.
- H. van’t Hoff (Dutch scientist) proposed a tetrahedral structure for carbon atom in
September of 1874. J. A. Le Bel (French scientist) published the same idea
independently in November of 1874.
- van’t Hoff was the first recipient of the Nobel Prize in Chemistry in 1901.
- In 1877, Hermann Kolbe (of the University of Leipzig), one of the most eminent
organic chemists of the time, criticized van’t Hoff’s publication on “The
Arrangements of Atoms in Space.” as a childish fantasy.
- He finds it more convenient to mount his Pegasus (飛馬座) (evidently taken
from the stables of the Veterinary College) and to announce how, on his bold
flight to Mount Parnassus (希臘中部的山;詩壇), he saw the atoms arranged in
space.
- The following information led van’t Hoff and Le Bel to the conclusion that the
spatial orientation of groups around carbon atoms is tetrahedral.