Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
8th Edition
ISBN: 9780134015187
Author: John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher: PEARSON
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Textbook Question
Chapter 18, Problem 18.39UKC
Threonine has two chiral centers. Draw L-threonine and indicate which carbon atoms are chiral. Which carbon atom is responsible for D and L configuration?
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Consider the structure of the tripeptide (in its fully protonated form) below.
H
H
H
+ I ||
H₂N-C-C-N-C-C-N-C-C-OH
1
I |
H CH₂ H CH₂
CH₂
T
C=O
OH
AA1
0=0
||
HC-CH3
CH3
AA2
AA3
0=C
1. Give the sequence of the tripeptide using the ONE-LETTER DESIGNATION (UPPERCASE LETTER) with NO spaces and symbols between each letter.
2. How many ionizable groups are there in the tripeptide? Give the numerical value (e.g., 10 not ten).
• pH 10: {Choices: -2, -1, 0, +1, +2}
3. Which amino acid residue has one ionizable group left upon forming the tripeptide? {Choices: AA1, AA2, AA3, none, all}
4. Give the net charge of the dominant structure of the tripeptide at the given pH values. The pK, values of the amino acids are given in Table 1.
• pH 4: {Choices: -2, -1, 0, +1, +2}
Draw tripeptide Lys-Thr-Glu at pH 7.4 and circle the six atoms that are restricted in the same plane.
IDENTIFY THE FUNCTIONAL GROUP PRESENT IN THESE COMPOUNDS.
A = ?
B = ?
C = ?
Chapter 18 Solutions
Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
Ch. 18.2 - Prob. 18.1PCh. 18.2 - Prob. 18.2PCh. 18.3 - Prob. 18.3PCh. 18.3 - Examine the ball-and-stick model of valine in the...Ch. 18.3 - Indicate whether each of the following molecules...Ch. 18.3 - Prob. 18.6PCh. 18.3 - Prob. 18.7KCPCh. 18.3 - Prob. 18.8PCh. 18.3 - Prob. 18.9PCh. 18.3 - Prob. 18.10P
Ch. 18.3 - Prob. 18.11PCh. 18.3 - Prob. 18.12PCh. 18.4 - The proteins collagen, bovine insulin, and human...Ch. 18.4 - Prob. 18.2CIAPCh. 18.4 - Prob. 18.13PCh. 18.4 - Prob. 18.14PCh. 18.5 - Valine is an amino acid with a nonpolar side...Ch. 18.5 - Tripeptides are composed of three amino acids...Ch. 18.5 - Prob. 18.17PCh. 18.5 - Identify the amino acids in the following...Ch. 18.5 - Prob. 18.19PCh. 18.5 - Prob. 18.3CIAPCh. 18.5 - Prob. 18.4CIAPCh. 18.5 - Two of the most complete (balanced) proteins...Ch. 18.6 - Prob. 18.6CIAPCh. 18.6 - Prob. 18.7CIAPCh. 18.6 - (a)What atoms are present in a planar unit in a...Ch. 18.6 - Prob. 18.21PCh. 18.6 - Prob. 18.22PCh. 18.7 - Prob. 18.23PCh. 18.7 - Prob. 18.24PCh. 18.7 - Complete the following two sentences with either...Ch. 18.7 - Prob. 18.26KCPCh. 18.8 - Which of the following pairs of amino acids can...Ch. 18.8 - Look at Table 18.3 and identify the type of...Ch. 18.8 - In Figure 18.3, identify the amino acids that have...Ch. 18.8 - Prob. 18.30PCh. 18.9 - Prob. 18.31PCh. 18.10 - Another endoprotease is trypsin. Trypsin...Ch. 18.10 - Prob. 18.33PCh. 18.10 - Prob. 18.8CIAPCh. 18.10 - Prob. 18.9CIAPCh. 18 - Draw the structure of the following amino acids,...Ch. 18 - Prob. 18.35UKCCh. 18 - Prob. 18.36UKCCh. 18 - Prob. 18.37UKCCh. 18 - Prob. 18.38UKCCh. 18 - Threonine has two chiral centers. Draw L-threonine...Ch. 18 - Name four biological functions of proteins in the...Ch. 18 - Prob. 18.41APCh. 18 - Prob. 18.42APCh. 18 - Prob. 18.43APCh. 18 - Prob. 18.44APCh. 18 - Prob. 18.45APCh. 18 - Prob. 18.46APCh. 18 - Prob. 18.47APCh. 18 - Draw leucine and identify any chiral carbon atoms...Ch. 18 - Prob. 18.49APCh. 18 - Prob. 18.50APCh. 18 - Is histidine hydrophilic or hydrophobic? Explain...Ch. 18 - Prob. 18.52APCh. 18 - At neutral pH, which of the following amino acids...Ch. 18 - Prob. 18.54APCh. 18 - Prob. 18.55APCh. 18 - Prob. 18.56APCh. 18 - Prob. 18.57APCh. 18 - Proteins are usually least soluble in water at...Ch. 18 - Prob. 18.59APCh. 18 - Prob. 18.60APCh. 18 - Prob. 18.61APCh. 18 - Prob. 18.62APCh. 18 - Prob. 18.63APCh. 18 - (a)Identify the amino acids present in the peptide...Ch. 18 - Prob. 18.65APCh. 18 - Prob. 18.66APCh. 18 - Prob. 18.67APCh. 18 - Prob. 18.68APCh. 18 - Prob. 18.69APCh. 18 - Prob. 18.70APCh. 18 - Prob. 18.71APCh. 18 - Prob. 18.72APCh. 18 - Prob. 18.73APCh. 18 - Prob. 18.74APCh. 18 - Prob. 18.75APCh. 18 - What kind of bond would you expect between chains...Ch. 18 - Is the bond formed between each pair in Problem...Ch. 18 - Prob. 18.78APCh. 18 - Prob. 18.79APCh. 18 - Prob. 18.80APCh. 18 - Prob. 18.81APCh. 18 - Prob. 18.82APCh. 18 - Prob. 18.83APCh. 18 - Prob. 18.84APCh. 18 - Prob. 18.85APCh. 18 - Prob. 18.86APCh. 18 - Prob. 18.87APCh. 18 - Prob. 18.88APCh. 18 - Give an example of a protein that has quaternary...Ch. 18 - Prob. 18.90APCh. 18 - Prob. 18.91APCh. 18 - Prob. 18.92APCh. 18 - Prob. 18.93APCh. 18 - Prob. 18.94APCh. 18 - Prob. 18.95APCh. 18 - Prob. 18.96APCh. 18 - Prob. 18.97APCh. 18 - Prob. 18.98CPCh. 18 - Prob. 18.99CPCh. 18 - Prob. 18.100CPCh. 18 - Prob. 18.101CPCh. 18 - Prob. 18.102CPCh. 18 - Prob. 18.103CPCh. 18 - Prob. 18.104CPCh. 18 - Prob. 18.105CPCh. 18 - Prob. 18.106CPCh. 18 - Prob. 18.107CPCh. 18 - Prob. 18.108CPCh. 18 - Prob. 18.109GPCh. 18 - Prob. 18.110GPCh. 18 - Prob. 18.111GPCh. 18 - Prob. 18.112GP
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- b) It's said that secondary structures form because of intra- and intermolecular hydrogen bonding involving the peptide bond. Describe what is going on to further stabilize secondary structure through these interactions.arrow_forwardH OH CH2OH D H ОН H الحزن ОН CH2OH ОН H ОН I Which of the following statements correctly describes this structure? (A) The monomer units are bonded by beta 1-2 glycosidic linkage. B The monomer units are bonded by alpha 1-2 glycosidic linkage. The monomer units are bonded by alpha 1-4 glycosidic linkage. The monomer units are bonded by beta 1-4 glycosidic linkage. H CH2OH H ОН H ОН H ОНarrow_forwardFollowing are structural formulas for cytosine and thymine. Draw two additional tautomeric forms for cytosine and three additional tautomeric forms for thymine.arrow_forward
- (a) What is the net charge at neutral pH of a tripeptide containing only alanine? (b) How does the total number of negative and positive charges change following hydrolysis of the tripeptide?arrow_forwardA pentapeptide on complete hydrolysis yields 3 moles of glycine (R=H), 1 mole of alanine (R=CH3) and 1 mole of serine (R=CH2OH). On partial hydrolysis, the fragments are ala-gly, gly-ala and gly-ser. The pentapeptide is negative to the Sanger reaction. Draw a possible structure for the pentapeptide.arrow_forwardHistidine has three ionizable groups. On the titration curve below, show: a) 2 molar equivalents of OH b) pka of the third ionizable group Histidine Titration 12.0 10.0 8.0 4 pH 6.0 4.0 2.0 0.0 Equivalents OHarrow_forward
- At a pH equal to the isoelectric point of alanine, the net charge on alanine is zero. Two structures can be drawn that have a net charge of zero, but the predominant form of alanine at its pI is zwitterionic.(a) Why is alanine predominantly zwitterionic rather than completely uncharged at its pI?(b) What fraction of alanine is in the completely uncharged form at its pI? Justify your assumptions.arrow_forwardUsing the picture provided, match the correct name of each of the functional groups highlighted in blue.arrow_forwardHow many different tripeptides can be formed from three different amino acids, glutamine, histidine, and lysine? Draw the possible structures. Using three-letter abbreviations, give the names for all of the possible tripeptides.arrow_forward
- Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure. a.) What product is formed when glutathione reacts with an oxidizing agent?b.) What is unusual about the peptide bond between glutamic acid and cysteine?arrow_forwardWhy is a thioester bond a “high-energy” bond?arrow_forwardDraw the two dipeptides possible when glutamine and cysteine undergo dehydration to form a peptide bond. Draw the dipeptides in zwitterionic form.arrow_forward
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