The quantitative differences in biological activity between the two enantiomers of a compound are sometimes quite large. For example, the D isomer of the drug isoproterenol, used to treat mild asthma, is 50 to 80 times more effective as a bronchodilator than the L isomer. Identify the chiral center in isoproterenol. Why do the two enantiomers have such radically different bioactivity?

Question

Chemistry

Ryan Bates

1 December, 15:29

The quantitative differences in biological activity between the two enantiomers of a compound are sometimes quite large. For example, the D isomer of the drug isoproterenol, used to treat mild asthma, is 50 to 80 times more effective as a bronchodilator than the L isomer. Identify the chiral center in isoproterenol. Why do the two enantiomers have such radically different bioactivity?

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Answers (1)

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Marisa Edwards · Answer 1

The Chiral center is show in the figure

Explanation:

If a carbon atom is bonded to four differents groups as in isoproterenol (-OH, - Ph, - H and - CH2-R), it is a chiral carbon, which means that the molecule has two enantiomers, D and L.

Each enantiomer will have a different bioactivity, the bioctivity is the interaction of the D or L enantiomer with a biological receptor which also is chiral. The two enantiomers have different bioactivity because each one interact different with the biological receptor.