Vladimir Prelog was a Croatian-Swiss chemist who lived from 1906 to 1998. He received his diploma in chemical engineering from the Czech Technical University in 1928. In the midst of World War II, he came to Switzerland to teach at ETH Zurich.
Vladimir Prelog was a Croatian-Swiss chemist who lived from 1906 to 1998. He completed his high school education in Zagreb in 1924, before moving to Prague, where he received his diploma in chemical engineering from the Czech Technical University in 1928. After spending some time in the industry, Prelog decided to return to academia (and to Croatia) as a lecturer at the University of Zagreb in 1935. In the midst of World War II, he was invited by his fellow Croatian chemist Leopold Ružička to come to Switzerland to work in the Organic Laboratory at ETH Zurich.
There he worked on the Cinchona alkaloids, especially quinine. His synthesis of the diamond-like hydrocarbon adamantane brought him international recognition. He elucidated the structures of antibiotics such as rifamycins used to treat tuberculosis. He received the Nobel Prize in Chemistry in 1975 for his research into the stereochemistry of organic molecules and reactions, i.e. the relationship between the structure of a chemical and its reactivity. An important area of his research concerned chiral molecules, formerly called asymmetric molecules. The word "chiral" comes from the Greek meaning "hand" and signifies that the molecules can have two forms differing from one another as the right hand does from the left. Prelog has done very significant research on reactions between chiral molecules, which is fundamental to understanding biological processes.
You may know the Cahn Ingold Prelog Convention (CIP Convention) to name the R-S or E-Z stereoisomers of a molecule! (See Figure 2 for a refresher) In pharmaceutical industries, 56% of the drugs currently in use are chiral molecules and 88% of the latter are marketed as racemic mixtures, consisting of an equimolar mixture of two enantiomers. Although the enantiomers of chiral drugs have the same chemical connectivity of atoms they can be metabolized very differently! Therefore, much effort goes towards the rigorous separation of the two enantiomers. This ensures that only the biologically active enantiomer is present in the final drug product. For example, it is the case for ibuprofen, where the (S)-enantiomer has the desired pharmacological activity (painkiller) while the (R)-enantiomer is completely inactive!
Did you know:
- that Prelog and Ružička (Nobel Prize 1939) were good friends and that the former succeeded as the head of the Organic Laboratory at ETH Zurich in 1957?
Figure 2: Structure of Quinine, Adamantane and Rifamycin. Adamantane was first synthesized by Prelog in 1941 with an overall yield of 0.16%!
Figure 3: What is a chiral center and how to attribute the right isomer with the CIP rule!