Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 24, Problem 8PP
Practice Problem 24.8
Glutathione is a tripeptide found in most living cells. Partial acid-catalyzed hydrolysis of glutathione yields two dipeptides, CG and one composed of E and C. When this second dipeptide was treated with DNFB, acid hydrolysis gave N-labeled glutamic acid.
(a) On the basis of this information alone, what structures are possible for glutathione?
(b) Synthetic experiments have shown that the second dipeptide has the following structure:
What is the structure of glutathione?
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(a) Provide four distinct forms of phenylalanine. (b) Rank the solubility of these forms in water. (c) Explain your ranking.
A tripeptide contains lysine (R= -(CH₂)4NH₂), phenylalanine (R= -CH₂C6H5) and glycine (R= -H). It was found that the tripeptide reacts with 2 moles
of DNFB to give compound A. When compound A was treated with SOCI2, glycine was activated. When hydrolyzed, both NH₂ groups of lysine were
found to be DNP-labelled. What is the structure of the tripeptide?
Select one:
H
(CH₂)2NH2
CH
NH
CH
H₂N
O
O
H₂N
H₂N
H₂N
C
(CH2)4NH2
CH
010
(CH2)4NH2
CH
C=O
CH,Ph
CH
NH
NH
NH
CH
CH,Ph
CH
H
010
CH
CH,Ph
CH
(CH2)4NH2
ΝΗ
NH
NH
NH
CH,Ph
CH
H
CH
COOH
H
CH
COOH
COOH
COOH
h) Specify the absolute (R/S) configuration of the amino group in structure IV.
(i) If the substituents in structures I, IV and V were identical (all OH or all NH2), which structure would result in a meso compound?
(j) If each hydroxy group for structures I, II and VI were replaced with another amino group, which compound would be made optically inactive?
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 1PPCh. 24 - Practice Problem 24.2 The guanidino group NHNHCNH2...Ch. 24 - Prob. 3PPCh. 24 - Prob. 4PPCh. 24 - Prob. 5PPCh. 24 - Prob. 6PPCh. 24 - Prob. 7PPCh. 24 - Practice Problem 24.8
Glutathione is a tripeptide...Ch. 24 - Prob. 9PPCh. 24 - Prob. 10PP
Ch. 24 - Prob. 11PPCh. 24 - Practice Problem 24.12 Show all steps in the...Ch. 24 - Practice Problem 24.13 The synthesis of a...Ch. 24 - Practice Problem 24.14
The terminal carboxyl...Ch. 24 - Prob. 15PPCh. 24 - Prob. 16PPCh. 24 - (a) Which amino acids in Table 24.1 have more than...Ch. 24 - Prob. 18PCh. 24 - 24.19 (a) On the basis of the following sequence...Ch. 24 - Prob. 20PCh. 24 - Prob. 21PCh. 24 - Prob. 22PCh. 24 - Prob. 23PCh. 24 - Prob. 24PCh. 24 - The enzyme lysozyme and its mechanism are...Ch. 24 - Prob. 2LGP
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