ORGANIC CHEMISTRY (LL)-W/ACCESS
10th Edition
ISBN: 9781259717536
Author: Carey
Publisher: MCG
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Question
Chapter 26.7, Problem 14P
Interpretation Introduction
Interpretation:
Assuming that each chirality center is L, the structural formula for each of the given dipeptides is to be shown in a manner that reveals the stereochemistry at the
Concept Introduction:
A peptide bond is an amide bond. A dipeptide contains two amino acids linked by a peptide bond.
It is formed between amino group of one amino acid the carboxyl group of the other amino acid.
The peptide structures are written, such that the amino group is at the left side and the carboxyl group is at the right side.
The left end of the peptide is called the N terminus and the right end is called the C terminus.
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An oligopeptide, 6 amino acids in length, was subjected to acid hydrolysis and yielded equimolar amounts of the following amino acids (in alphabetical order):
Arg Gln Lys Met Thr Tyr
Based on the following separate treatments, which amino acid is in position #5 of this
sequence?
a. Cyanogen bromide treatment had no effect.
b. Trypsin treatment yielded a dipeptide, a tripeptide and free arginine. The tripeptide had a net positive charge at pH 7.
c. Chymotrypsin treatment yielded a dipeptide and a tetrapeptide. The dipeptide had a net
charge of zero at pH 5.
d. The phenylthiohydantoin derivative released by one round of Edman degradation was
PTH-Thr.
A decapeptide has the following amino acid composition.
Ala2, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val
Partial hydrolysis yields the following tripeptides.
Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala + Lys-Val-Phe + Val-Phe-Gly
One round of Edman degradation yields a lysine phenylthiohydantoin. From this information, deduce the primary structure of this decapeptide.
. True/ False
A. Amino acids found in the living systems are generally in the D-form
B. The R-group attached to alfa carbon atom of amino acids are unique for each amino acids.
C. Of the 20 essential amino acids, glycine is the only amino acid which is achiral.
D. Ions of heavy metals Hg2+ or Pb2+ denature proteins by combining with the amino groups.
E. Denaturation of protein involves the breakdown of secondary, tertiary and quaternary structure.
F. Cysteine is the only amino acid that can form a disulfide bridge.
G. Both the poly saccharides and proteins are polymers.
H. Hydrogen bonding is responsible for the secondary structure of Proteins.
I. When proteins are hydrolyzed, smaller peptides and amino acids are produced.
J. When simple lipids are hydrolyzed glycerol an alcohol as well as fatty acids and their salts are produced.
Chapter 26 Solutions
ORGANIC CHEMISTRY (LL)-W/ACCESS
Ch. 26.1 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Prob. 3PCh. 26.3 - Prob. 4PCh. 26.3 - Prob. 5PCh. 26.4 - Prob. 6PCh. 26.4 - Prob. 7PCh. 26.4 - Prob. 8PCh. 26.5 - Prob. 9PCh. 26.6 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.7 - Prob. 13PCh. 26.7 - Prob. 14PCh. 26.7 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Prob. 17PCh. 26.9 - Prob. 18PCh. 26.10 - Digestion of the tetrapeptide of Problem 26.18...Ch. 26.12 - Prob. 20PCh. 26.12 - Prob. 21PCh. 26.15 - Prob. 22PCh. 26.15 - Prob. 23PCh. 26.16 - Prob. 24PCh. 26.17 - Prob. 25PCh. 26.18 - Prob. 26PCh. 26 - Prob. 27PCh. 26 - Prob. 28PCh. 26 - Prob. 29PCh. 26 - Prob. 30PCh. 26 - Prob. 31PCh. 26 - Prob. 32PCh. 26 - Prob. 33PCh. 26 - Prob. 34PCh. 26 - Prob. 35PCh. 26 - Prob. 36PCh. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - Prob. 39PCh. 26 - Prob. 40PCh. 26 - If you synthesized the tripeptide Leu-Phe-Ser from...Ch. 26 - Prob. 42PCh. 26 - Prob. 43PCh. 26 - Prob. 44PCh. 26 - Prob. 45DSPCh. 26 - Prob. 46DSPCh. 26 - Prob. 47DSPCh. 26 - Prob. 48DSPCh. 26 - Prob. 49DSPCh. 26 - Prob. 50DSP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
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- Prepare valine from the corresponding: a) aldehyde, b) halocarboxylic acid, c) keto acid, d) nitro acid.arrow_forwardAs a genetic engineer, you have been given the following task:alter a protein’s structure by converting a specific amino acidsequence that forms an extended a-helix to one that formsa b-barrel. What types of amino acid are probably in thea-helix, and which ones would you need to substitute?arrow_forwardA normal polypeptide and a mutant of the polypeptide were hydrolyzed by an endopeptidase under the same conditions. The normal and mutant poly peptide differ by one amino acid. The fingerprints of the peptides obtained from the two polypeptides are shown below. What kind of amino acid substitution occurred as a result of the mutation? (That is, is the substituted amino acid more or less polar than the original amino acid? Is its pI lower or higher?)arrow_forward
- Show the steps in the synthesis of the tetrapeptide Leu-Phe-Ala-Val, using Merrifield’s method.arrow_forwardConsider the peptide Trp-Arg-Glu-Cys-Gly-Tyr. For the drawings requested below, please show them in zig-zag style, from amino to carboxy terminus, with correct stereochemistry please highlight the part has been change Draw the predominant form at pH = 2 Draw the predominant form at pH = 5 Draw the predominant form at pH = 7 Draw the predominant form at pH = 12arrow_forwardWhat percentage of the a-amino group of lysine will be protonated at its pI? < 25% 50% > 75% a. Answer the same question for the e-amino group of lysine.arrow_forward
- A tetrapeptide is given as: Ser-Lys-Ala-Phe. Which statement is true? a. The listing should be in alphabetical order. b. There are four peptide bonds because there are four amino acids. c. The serine provided a nitrogen for the peptide bond. d. The N-terminus is serine (Ser).arrow_forwardDraw three-dimensional representations of the following amino acids.(a) l-phenylalaninearrow_forwardDetermine the amino acid sequence of a polypeptide from the following data:Acid-catalyzed hydrolysis gives Ala, Arg, His, 2 Lys, Leu, 2 Met, Pro, 2 Ser, Thr, and Val.Carboxypeptidase A releases Val.Edman’s reagent releases PTH-Leu.Trypsin-catalyzed hydrolysis gives three peptides and a single amino acid:1. Arg, Leu, Ser 3. Lys2. Met, Pro, Ser, Thr, Val 4. Ala, His, Lys, Metarrow_forward
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