Biochemistry: Concepts and Connections (2nd Edition)
2nd Edition
ISBN: 9780134641621
Author: Dean R. Appling, Spencer J. Anthony-Cahill, Christopher K. Mathews
Publisher: PEARSON
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Chapter 8, Problem 16P
Enalapril is an anti-hypertension “pro-drug" (i.e., a drug precursor) that is inactive until the ethyl ester (arrow in figure) is hydrolyzed by esterases present in blood plasma. The active drug is the dicarboxylic acid (“enalaprilat") that results from this hydrolysis reaction.
a. Enalapril is administered in pill form, but enalaprilat must be administered intravenously. Why do you suppose enalapril works as a pill but enalaprilat does not?
b. Enalaprilat is a competitive inhibitor of the angiotensin-converting enzyme (ACE), which cleaves the blood-pressure regulating peptide angiotensin I. ACE has a KM = 521 µM for angiotensin I, which is present in plasma at a concentration of 75 µM When enalaprilat is present at 2.4 nM, the activity of ACE in plasma is 10% of its uninhibited activity. What is the value of KI for enalaprilat?
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Enalapril is an anti-hypertension "prodrug" (i.e, a drug precursor)
that is inactive until the ethyl ester (arrow in figure) is hydrolyzed by
esterases present in blood plasma. The active drug is the dicarboxylic
acid ("enalaprilat") that results from this hydrolysis reaction.
(a) Enalapril is administered in pill form, but enalaprilat must be
administered intravenously. Why do you suppose enalapril works as
a pill, but enalaprilat does not?
EtOOC
-NH
CH3
HOOC
Enalapril
(b) Enalaprilat is a competitive inhibitor of the angiotensin-converting
enzyme (ACE), which cleaves the blood-pressure regulating peptide
angiotensin. ACE has a KM = 12 µM for angiotensin, which is
present in plasma at a concentration of 75 µM. When enalaprilat is
present at 2.4 nM, the activity of ACE in plasma is 10% of its uninhib-
ited activity. What is the value of K; for enalaprilat?
Enalapril is an anti-hypertension “pro-drug” (i.e., a drug precursor) that isinactive until the ethyl ester (arrow in figure) is hydrolyzed by esterases present in blood plasma. The active drug is the dicarboxylic acid (“enalaprilat”) that results from this hydrolysis reaction.(a) Enalapril is administered in pill form, but enalaprilat must be administered intravenously. Why do you suppose enalapril works as a pill but enalaprilat does not? (b) Enalaprilat is a competitive inhibitor of the angiotensin-convertingenzyme (ACE), which cleaves the blood-pressure regulating peptideangiotensin I. ACE has a KM = 52 μM for angiotensin I, which is presentin plasma at a concentration of 75 μM. When enalaprilat is presentat 2.4 nM, the activity of ACE in plasma is 10% of its uninhibitedactivity. What is the value of K1 for enalaprilat?
This is remdesivir, one of the drugs being used in the treatment of COVID-19.
Label the indicated carbons as R, S, or neither.
b);
NH2
HO
OH
Chapter 8 Solutions
Biochemistry: Concepts and Connections (2nd Edition)
Ch. 8 - Prob. 1PCh. 8 - The enzyme urease catalyzes the hydrolysis of urea...Ch. 8 - An enzyme contains an active site aspartic acid...Ch. 8 - The folding and unfolding rate constants for a...Ch. 8 - In some reactions, in which a protein molecule is...Ch. 8 - Would you expect an “enzyme” designed to bind to...Ch. 8 - The initial rate for an enzyme-catalyzed reaction...Ch. 8 - a. If the total enzyme concentration in Problem 7...Ch. 8 - Prob. 9PCh. 8 - Prob. 10P
Ch. 8 - The following data describe the catalysis of...Ch. 8 - At 37 oC, the serine protease subtilisin has kcat...Ch. 8 - The accompanying figure shows three...Ch. 8 - The steady-state kinetics of an enzyme are studied...Ch. 8 - The same enzyme as in Problem 14 is studied in the...Ch. 8 - Enalapril is an anti-hypertension “pro-drug"...Ch. 8 - Initial rate data for an enzyme that obeys...Ch. 8 - Prob. 18PCh. 8 - Suggest the effects of each of the following...Ch. 8 - The inhibitory effect of an uncompetitive...Ch. 8 - Prob. 21PCh. 8 - Prob. 22PCh. 8 - Prob. 23PCh. 8 - In kinetics experiments, the hydrolysis of the...
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