Chapter 29: Q10P (page 1162)
Which of the following amines can be used to resolve a racemic mixture of amino acids?
(a)

(b)

(c)

(d)

Short Answer
Answer
(c)

(d)

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Chapter 29: Q10P (page 1162)
Which of the following amines can be used to resolve a racemic mixture of amino acids?
(a)

(b)

(c)

(d)

Answer
(c)

(d)

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Draw the organic products formed in each reaction.

a.

b.

c.

d.

e.

f.
Draw the other three stereoisomers of L-isoleucine, and label the stereogenic centers as R or S.
The enolate derived from diethyl acetamidomalonate is treated with each of the following alkyl halides. After hydrolysis and decarboxylation, what amino acid is formed?
a. CH3I
b. (CH3)2CHCH2Cl
c. CH3CH2CH(CH3)Br
Consider two molecules of a tetrapeptide composed of only alanine residues. Draw the hydrogen bonding interactions that result when these two peptides adopt a parallel β-pleated sheet arrangement. Answer this same question for the antiparallel β-pleated sheet arrangement.
a.(S)-Penicillamine, an amino acid that does not occur in proteins, is used as a copper chelating agent to treat Wilson’s disease, an inherited defect in copper metabolism.
(R)-Penicillamine is toxic, sometimes causing blindness. Draw the structures of (R) and (S)-penicillamine.
b. What disulfide is formed from oxidation of L-penicillamine?
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