Problem 1Nelfinavir is a small-molecule treatment for HIV that acts by inhibiting HIV protease, a critical enzyme forviral replication.OH 2CHO.OH 3Nelfinavir"BUHN(a) The pk, of the protonated form tertiary amine (1) in nelfinavir is 6.00. In general, the pKs ofprotonated amines (i.e., ammonium ions) range between 9 and 11. How would you rationalize thisapparent discrepancy?(b) The pK,s of the two -OH groups (2 and 3) are 11.06 and "17, respectively. Briefly explain why thepK, of alcohol 2 is 6 orders of magnitude lower than that of alcohol 3.(c) Draw the form (i.e., protonation state) of nelfinavir that you expect to predominate in the stomach,where the pH is between 1.5 and 3.5? Briefly justify your answer.(d) The pH of saliva is about 6.5. What two forms of nelfinavir would you expect to predominate insaliva? What are their relative ratios?

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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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Problem 1. Greco et al. have developed a regression curve fitting package in 1982 and tested it on Vp vs. [S] profiles of Hexosaminidase enzyme (see the figure below). The reactions rates were experimentally measured at various substrate concentrations in the presence or absence of an inhibitor. P-nitrophenyl-N-acetyl-ß-D- glucosaminide (NAG) is the substrate. 2-acetamido-2,4-dideoxy-4-fluoro-D-galactono-1,5-lactone (ADFGL) is the inhibitor. 1 0.9 0.8 -- No Inhibitor 0.7 - 0.2 mM Inhibitor 0.6 0.5 0.4 0.3 0.2 0.1 2 [S] (mM) Using the data given in the Figure, answer the following questions. A) Determine Vmax and Km of the reaction in the absence of inhibitor. B) Determine the inhibition type? C) Determine the equilibrium constant (K;) associated with the enzyme-inhibitor complex. V, (mM/s)

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