Chapter 29: Q7P (page 1158)
What amino acid is formed when CH3CONHCH(CO2Et)2is treated with the following series of reagents:

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Chapter 29: Q7P (page 1158)
What amino acid is formed when CH3CONHCH(CO2Et)2is treated with the following series of reagents:

Answer

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Explain why the pKaof the -NH3+group of an -amino acid is lower than the pKaof the ammonium ion derived from a amine . For example, pKaof the group of alanine is 9.87 but the pKaof is 10.63.
Draw the product formed when the following amino acid is treated with each reagent: (a); (b), pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e).

Draw the organic products formed in each reaction.

a.

b.

c.

d.

e.

f.
Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin,
appeared in Section 22.6B.)
a. Draw the structure of the tripeptide A-A-A, and label the two ionizable functional groups.
b. What is the predominant form of A-A-A at pH=1?
c. The values for the two ionizable functional groups (3.39 and 8.03) differ considerably from the values of alanine (2.35 and 9.87;see table 29.1). Account for the observed differences.
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