Chapter 5: Q.49 (page 207)
Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.
ethambutol
Short Answer
Following is the structure of (S,S)-ethambutol:
Chapter 5: Q.49 (page 207)
Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.
ethambutol
Following is the structure of (S,S)-ethambutol:
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Get started for freeWhat is the maximum number of stereoisomers possible for each compound?
a.
b.
c.
Determine if each compound is identical to or an enantiomer of A.
a.
b.
c.
a. Locate the stereogenic centres in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure.
b. Label each stereogenic centre as R or S.
A molecule is achiral if it has a plane of symmetry in any conformation. Each of the following conformations does not have a plane of symmetry, but rotation around a carbonโcarbon bond forms a conformation that does have a plane of symmetry. Draw this conformation for each molecule.
a.
b.
Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, has been used as an unsanctioned anticancer drug both within and outside of the United States. One hydrolysis product formed from amygdalin is mandelic acid, used in treating common skin problems caused by photo-aging and acne.
a. How many stereogenic centres are present in amygdalin? What is the maximum number of stereoisomers possible?
b. Draw both enantiomers of mandelic acid and label each stereogenic centre as R or S.
c. Pure (R)-mandelic acid has a specific rotation of โ154. If a sample contains 60% of the R isomer and 40% of its enantiomer, what is of this solution?
d. Calculate the ee of a solution of mandelic acid having = +50. What is the percentage of each enantiomer present?
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