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PMSF (phenylmethylsulfonyl fluoride) is an inactivator of serine proteases. It is commonly used in the production of protein for experimental study; it prevents cellular proteases from digesting the protein of interest. The structure of PMSF is: (15 points)
a. Starting with the framework of a serine protease active site provided below, show a complete curved arrow mechanism for how PMSF inactivates the enzyme. In your drawing, also complete the missing portions of the enzyme, and show all important interactions in the active site. Draw any H-bonds as dotted lines.
b. PMSF is a (choose all that apply):
i. Transition state analog
ii. Substrate analog
iii. Product analog
iv. Competitive inhibitor
v. Uncompeititive inhibitor
vi. Mixed inhibitor
c. True or false? Lowering the pH of the solution would alter binding by PMSF. In a single sentence, explain how you arrived at your answer.
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