Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 27, Problem 27.62AP
Interpretation Introduction
(a)
Interpretation:
The explanation for iodoacetic acid reaction with side chain thiol group of a cysteine residue is to be stated. The reason as to why this reaction is necessary before sequencing is to be stated.
Concept introduction:
The reagent DTT is known as dithiothreitol and is a common redox reagent. It is also known as Cleland’s reagent. It is relatively not a stable compound due to air oxidation. It is used as a deprotecting group and to break the disulfide bond in protein.
Interpretation Introduction
(b)
Interpretation:
The product obtained on oxidation of disulfide bond with
Concept introduction:
The compound hydrogen peroxide represented by
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Treatment of a new protein with dansyl chloride reveals two (2) dansyl-labelled derivatives of amino acids, alanine and methionine. What can you deduce about the structure of the proteinfrom these results?
indicate the RIGHT alternative:
(a) The Zwitterion form of an amino acid exists only at a point pH value.
(b) In a peptide bond there is free rotation at the C-N bond.
(c) In a polypeptide, the terminal carboxyl group may be present in its amide form.
(d) At a pH greater than pI, an amino acid tends to move towards the cathode in an electrophoresis.
(e) At any pH below pI, the predominant form of an amino acid is negatively charged.
(a) The two most acidic hydrogens of uracil have pKa’s of 9.5 and 14.2, respectively. Match these pKa’s with the hydrogens in the structural formula and provide structures for the most stable resonance contributors of the monoanion and the dianion.(b) The pKa of the conjugate acid of triethylamine is 10.4. Is triethylamine a strong enough base to convert uracil to its monoanion? To its dianion?
Chapter 27 Solutions
Organic Chemistry
Ch. 27 - Prob. 27.1PCh. 27 - Prob. 27.2PCh. 27 - Prob. 27.3PCh. 27 - Prob. 27.4PCh. 27 - Prob. 27.5PCh. 27 - Prob. 27.6PCh. 27 - Prob. 27.8PCh. 27 - Prob. 27.9PCh. 27 - Prob. 27.10PCh. 27 - Prob. 27.11P
Ch. 27 - Prob. 27.12PCh. 27 - Prob. 27.13PCh. 27 - Prob. 27.14PCh. 27 - Prob. 27.15PCh. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Prob. 27.25PCh. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - Prob. 27.43APCh. 27 - Prob. 27.44APCh. 27 - Prob. 27.45APCh. 27 - Prob. 27.46APCh. 27 - Prob. 27.47APCh. 27 - Prob. 27.48APCh. 27 - Prob. 27.49APCh. 27 - Prob. 27.50APCh. 27 - Prob. 27.51APCh. 27 - Prob. 27.52APCh. 27 - Prob. 27.53APCh. 27 - Prob. 27.54APCh. 27 - Prob. 27.55APCh. 27 - Prob. 27.56APCh. 27 - Prob. 27.57APCh. 27 - Prob. 27.58APCh. 27 - Prob. 27.59APCh. 27 - Prob. 27.60APCh. 27 - Prob. 27.61APCh. 27 - Prob. 27.62APCh. 27 - Prob. 27.63APCh. 27 - Prob. 27.64APCh. 27 - Prob. 27.65APCh. 27 - Prob. 27.66APCh. 27 - Prob. 27.67APCh. 27 - Prob. 27.68APCh. 27 - Prob. 27.69APCh. 27 - Prob. 27.70APCh. 27 - Prob. 27.71APCh. 27 - Prob. 27.72APCh. 27 - Prob. 27.73APCh. 27 - Prob. 27.74APCh. 27 - Prob. 27.75APCh. 27 - Prob. 27.76APCh. 27 - Prob. 27.77APCh. 27 - Prob. 27.78APCh. 27 - Prob. 27.79APCh. 27 - Prob. 27.80APCh. 27 - Prob. 27.81APCh. 27 - Prob. 27.82APCh. 27 - Prob. 27.83AP
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- only question (b)arrow_forwardA 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 COOHarrow_forward(b) Describe how the charge of some amino groups in a protein might differ at pH 9.0 and pH 5.0. the charge on the amino group will differ at pH 5 and pH 9 which will depend on the pKa of the amino acid. (c) Describe how the charge of some carboxyl groups in a protein might differ at pH 9.0 and pH 5.0. charge on carboxyl group will differ at pH 5 and pH 9 which will depend on the pKa of the amino acid. (d) Given your answers to parts (b) and (c), what kind of intramolecular interactions in beta-galactosidase are most likely to be affected by a change in pH from 9.0 to 5.0? (e) Could the interactions you mention in part (d) affect the catalytic activity of beta-galactosidase?arrow_forward
- Draw the structure of the tetrapeptide Asp-Arg-Val-Tyr. Please show the appropriate stereochemistry of the natural amino acids in the resulting peptide. Please draw all ionizable groups in their neutral form.arrow_forwardWhat is the Answer for (a.) ?arrow_forward(a) Isoleucine has been prepared by the following sequence of reactions. Give the structure of compounds A through D isolated as intermediates in this synthesis.(b) An analogous procedure has been used to prepare phenylalanine. What alkyl halide would you choose as the starting material for this synthesis?arrow_forward
- An amino acid mixture of phenylalanine, glycine and glutamic acid is to be separated bypaper chromatography. The solvent is less polar than water. Which of these amino acids will have the highest Rf value and which the lowest? Explain. Treatment of a new protein with dansyl chloride reveals two (2) dansyl-labelled derivatives of amino acids, alanine and methionine. What can you deduce about the structure of the protein from these results? Name the amino acids that contribute atoms to both purine and pyrimidine rings.arrow_forwardThe amino acid (S)-alanine has the physical characteristics listed under the structure. Label each of the following as optically active or inactive: a solution of pure (S)- alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.arrow_forwardQ1arrow_forward
- Now let's consider histidine as a free amino acid in aqueous solution. a) Draw the most likely structure of histidine under biochemical standard state conditions. b) Given that free histidine has the following three pKa values, assign each to its corresponding acidic hydrogen or conjugate base in your structure from part a). pK1 = 1.7, pKa2 = 6.0, pK23 = 9.1 c) For each pKa, give the corresponding expression for the equilibrium constant. It helps to write out the chemical equation for each.arrow_forwardPart a) Draw the peptide K-E-S. Part b) How can you estimate the pI of the peptide?arrow_forwardSubject-advance chemistryarrow_forward
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