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ProblemSet5 - Biochemistry 704 Problem Set 5 Due 1 Circle...

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Biochemistry 704 Problem Set 5 Due 03/25/2008 1. Circle the compound below that has the most stable disulfide bond (that is, the one most difficult to reduce). S S S S S S 1 2 3 Explain briefly why each of the other two disulfide bonds is less stable. 2. Proteins can suffer irreversible damage at high pH. For example, asparagine residues can degrade spontaneously to form aspartate and “isoaspartate” residues. These two products are formed by the hydrolysis of a common intermediate, i . NH NH 2 O O N H O NH O O N H NH O O O N H i Draw the structure of i .
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page 2 of 5 3. The exchange of deuterium between [D 6 ]acetone and solvent H 2 O is catalyzed by amines. D 3 C CD 3 O H 3 C CH 3 O amine 3 H 2 O + + 3 D 2 O Diamine 4 is a much better catalyst for this reaction than is monoamine 5 . N N NH 2 5 4 a. Propose a mechanism for the exchange reaction as catalyzed by diamine 4 . b. Diamine 6 is an even better catalyst than diamine 4 for the exchange reaction.
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