HW09Key - Look at the structure of lovastatin, and...

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Graded Homework Problem #09 – Answer Key (Problem worth 20 points; each box worth 4 points) The statins form a class of drugs that are used to lower cholesterol in the blood of people who are at risk of developing heart disease. They work to lower cholesterol by inhibiting the enzyme HMG–CoA reductase, which is involved in the rate-limiting step of cholesterol biosynthesis. The first statin to be approved for use in the U.S. was lovastatin. The structure of lovastatin is shown below. Note the use of wedges and dashed wedges to indicate absolute stereochemistry.
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Unformatted text preview: Look at the structure of lovastatin, and determine the total number of stereoisomers possible for this molecule. Write your answer in the appropriate box. Several (but not all) of the chiral centers in lovastatin are marked with arrows. In the box associated with each arrow, indicate the stereochemical configuration of the chiral center as ( R ) or ( S ) . Total number of stereoisomers possible = O O H O HO O * * * * * * * * 256 = 2 8 (The 8 chiral centers are marked in the structure below) 1 2 3 4 ( S ) 1 2 3 4 ( R ) 1 2 3 4 ( R ) 1 2 3 4 ( R )...
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