Chapter 29: Q51P (page 1194)
Draw the structure for each peptide:
(a) Phe–Ala;
(b) Gly–Gln;
(c) Lys–Gly;
(d) R-H
Short Answer
a.
b.
C.
d.
Chapter 29: Q51P (page 1194)
Draw the structure for each peptide:
(a) Phe–Ala;
(b) Gly–Gln;
(c) Lys–Gly;
(d) R-H
a.
b.
C.
d.
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Get started for freeAn 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.
Outline the steps needed to synthesize the tetrapeptideAla–Leu–Ile–Gly using the Merrifield technique.
Draw each polymer in Problem 30.29 using the shorthand representation shown in Figure 30.2.
Propose a structure consistent with each set of data.
a. Compound J: molecular ion at 72; IR peak at 1710 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\); \({}^{\bf{1}}{\bf{H}}\)-NMR data (ppm) at 1.0 (triplet, 3 H), 2.1 (singlet, 3 H), and 2.4 (quartet, 2 H)
b. Compound K: molecular ion at 88; IR peak at 3600–3200 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\); \({}^{\bf{1}}{\bf{H}}\)-NMR data (ppm) at 0.9 (triplet, 3 H), 1.2 (singlet, 6 H), 1.5 (quartet, 2 H), and 1.6 (singlet, 1 H)
Draw the organic products formed in each reaction
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