Chapter 29: Q40. (page 1193)
What alkyl halide is needed to synthesize each amino acid from diethyl acetamidomalonate: (a)Asn; (b)His; (c)Trp?
Short Answer



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Chapter 29: Q40. (page 1193)
What alkyl halide is needed to synthesize each amino acid from diethyl acetamidomalonate: (a)Asn; (b)His; (c)Trp?



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Draw the products of each reaction.
(a)
(b)

(c)

(d)
Devise a synthesis of each amino acid from acetaldehyde:
(a) Glycine;
(b) Alanine.
Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.
a. Val–Glu
b. Gly–His–Leu
c. M–A–T–T
As shown in Mechanism 29.2, the final steps in the Edman degradation result in rearrangement of a thiazolinone to an N-phenylthiohydantoin. Draw a stepwise mechanism for this acid-catalyzed reaction.

An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glue (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile-Leu in addition to other products. Deduce the structure of the octapeptide and fragments A-D.
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