Enalapril is an anti-hypertension "prodrug" (i.e, a drug precursor)that is inactive until the ethyl ester (arrow in figure) is hydrolyzed byesterases present in blood plasma. The active drug is the dicarboxylicacid ("enalaprilat") that results from this hydrolysis reaction.(a) Enalapril is administered in pill form, but enalaprilat must beadministered intravenously. Why do you suppose enalapril works asa pill, but enalaprilat does not?EtOOC-NHCH3HOOCEnalapril(b) Enalaprilat is a competitive inhibitor of the angiotensin-convertingenzyme (ACE), which cleaves the blood-pressure regulating peptideangiotensin. ACE has a KM = 12 µM for angiotensin, which ispresent in plasma at a concentration of 75 µM. When enalaprilat ispresent 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?

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Biochemistry

9th Edition

ISBN:9781319114671

Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.

Chapter1: Biochemistry: An Evolving Science

Section: Chapter Questions

Problem 1P

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