Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 26.SE, Problem 46AP
Interpretation Introduction
Interpretation:
The amide bonds that are cleaved by trypsin and by chymotrypsin in the polypeptide, Phe-Leu-Met-Lys-Tyr-Asp-Gly-Arg-Val-Ile-Pro-Tyr, are to be given.
Concept introduction:
Partial hydrolysis of a peptide can be carried out using enzymes which are specific in their action. The enzyme trypsin catalyses the hydrolysis of peptides only at the carboxyl side of the basic amino acids arginine ald lysine. The enzyme chymotrypsin cleaves only at the carboxyl side of the aryl substituted amino acids phenylalanine, tyrosin and tryptophan.
To give:
The amide bonds that are cleaved by trypsin and by chymotrypsin in the polypeptide, Phe-Leu-Met-Lys-Tyr-Asp-Gly-Arg-Val-Ile-Pro-Tyr.
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Check out a sample textbook solutionStudents have asked these similar questions
-NHCHÖNHCH
ਸਾਲ
R
&
C-NHCHC-
R'
CH₂
T
CH₂-S-CH3
Arrow-pushing Instructions
AOC XT
H :O:
1. BrCN
2. H₂O
NHCH-C
NHCH-C-NCHC-
H₂C 0: R'
H₂
NHCHCNI
R
:0-H
I
H
0=0
Proteins can be cleaved specifically at the amide bond on the carboxyl side of methionine residues by reaction with cyanogen bromide (above). Cleavage proceeds by a four-stage mechanism. The third stage is an hydrolysis reaction that cleaves the peptide
chain. At the end of this stage, the carboxyl group of the former methionine becomes part of a lactone (cyclic ester) ring. Draw curved arrows for the first step of this stage.
-NHCHÖNHCH-C-OH
CH₂
CH₂-OH
+
{}
H₂NCC-
R'
The structure among the following that represents an amide (peptide) bond is:
N H
N-H
-C-O-
-C-O-H
A
B
он
C-0-
-C-N-
D
structure A
structure D
structure B
structure C
|
15. How is an amide converted to an anhydride?
Water with strong acid → PCl5 → Carboxylic Acid
PCl5 → Water with strong acid → Carboxylic Acid
Water with strong acid → Carboxylic Acid → PCl5
PCl5 → Carboxylic Acid → Water with strong acid
Chapter 26 Solutions
Organic Chemistry
Ch. 26.1 - How many of the -amino acids shown in Table 26-1...Ch. 26.1 - Prob. 2PCh. 26.1 - Prob. 3PCh. 26.2 - Hemoglobin has pI=6.8. Does hemoglobin have a net...Ch. 26.3 - Show how you could prepare the following -amino...Ch. 26.3 - What alkyl halides would you use to prepare the...Ch. 26.3 - Prob. 7PCh. 26.4 - There are six isomeric tripeptides that contain...Ch. 26.4 - Draw the structure of M-P-V-G, and indicate its...Ch. 26.5 - Prob. 10P
Ch. 26.5 - Prob. 11PCh. 26.6 - The octapeptide angiotensin II has the sequence...Ch. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Give the amino acid sequence of hexapeptides that...Ch. 26.7 - Prob. 16PCh. 26.7 - Write all five steps required for the synthesis of...Ch. 26.10 - Prob. 18PCh. 26.SE - Identify the following amino acids:Ch. 26.SE - Prob. 20VCCh. 26.SE - Isoleucine and threonine are the only two amino...Ch. 26.SE - Prob. 22VCCh. 26.SE - Give the sequence of the following tetrapeptide:Ch. 26.SE - Prob. 24MPCh. 26.SE - The chloromethylated polystyrene resin used for...Ch. 26.SE - Prob. 26MPCh. 26.SE - Prob. 27MPCh. 26.SE - Prob. 28MPCh. 26.SE - Except for cysteine, only S amino acids occur in...Ch. 26.SE - Prob. 30APCh. 26.SE - Prob. 31APCh. 26.SE - Show the structures of the following amino acids...Ch. 26.SE - Prob. 33APCh. 26.SE - Using both three- and one-letter codes for amino...Ch. 26.SE - Prob. 35APCh. 26.SE - Show how you could use the acetamidomalonate...Ch. 26.SE - Prob. 37APCh. 26.SE - Show how you could prepare the following amino...Ch. 26.SE - Prob. 39APCh. 26.SE - Predict the product of the reaction of valine with...Ch. 26.SE - Prob. 41APCh. 26.SE - Prob. 42APCh. 26.SE - Propose two structures for a tripeptide that gives...Ch. 26.SE - Show the steps involved in a synthesis of...Ch. 26.SE - Prob. 45APCh. 26.SE - Prob. 46APCh. 26.SE - Prob. 47APCh. 26.SE - Which of the following amino acids are more likely...Ch. 26.SE - Leuprolide is a synthetic nonapeptide used to...Ch. 26.SE - The -helical parts of myoglobin and other proteins...Ch. 26.SE - Prob. 51APCh. 26.SE - Cytochrome c is an enzyme found in the cells of...Ch. 26.SE - Prob. 53APCh. 26.SE - Prob. 54APCh. 26.SE - Prob. 55APCh. 26.SE - What is the structure of a nonapeptide that gives...Ch. 26.SE - Oxytocin, a nonapeptide hormone secreted by the...Ch. 26.SE - Aspartame, a nonnutritive sweetener marketed under...Ch. 26.SE - Prob. 59APCh. 26.SE - Prob. 60APCh. 26.SE - Prob. 61APCh. 26.SE - Prob. 62AP
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