14D_f09_finalA

14D_f09_finalA - Chemistry 14D Fall 2009 Final Exam Part A...

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Chemistry 14D Fall 2009 Final Exam Part A Page 1 Page 1 score = Simvastatin (shown at right) is a cholesterol-lowering drug that works by inhibiting HMG-CoA reductase, an enzyme that converts HMG-CoA into mevalonate. It is the lactone (cyclic ester) moiety of simvastatin that provides the inhibitory effects. CH 3 CH 3 O O H O HO Questions 1 and 2 refer to a potential reaction for the inhibition of HMG-CoA reductase (abbreviated as Enz-NH 2 ), shown below. Enz-NH 3 + is a weak acid. O R HO O Enz-NH 2 Enz-NH 3 OH HO R H N O Enz 1. (8) Write a mechanism for this reaction. 2. (2) Consider the equilibrium between simvastatin and the inhibited enzyme: R HO O Enz-NH 2 OH HO R H N O Enz + For this equilibrium (circle one): K eq < 1 K eq ~ 1 K eq > 1
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Chemistry 14D Fall 2009 Final Exam Part A Page 2 Page 2 score = 3. (4) The enzyme active site might also contain a serine side chain (Enz-CH 2 OH), in which case the enyzme inhibition product is an ester as shown below. O R HO O Enz-CH 2 OH OH HO R OCH 2 Enz O Enz-NH 2 vs. OH HO R N O H Enz Observed product Not formed Complete this sentence in twenty words or less : Even though the observed product is an ester, the reaction of simvastatin with Enz-CH 2 OH is less favorable than the reaction of simvastatin with Enz- NH 2 because. ..
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14D_f09_finalA - Chemistry 14D Fall 2009 Final Exam Part A...

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