Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 26.SE, Problem 50AP
The α-helical parts of myoglobin and other proteins stop whenever a proline residue is encountered in the chain. Why is proline never present in a protein α helix?
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Draw Tryptophan in a peptide bond. Explain all of the bonds using valence bond theory (VBT). Next, explain where VBT fails and how molecular orbital theory is a better description of key regions of this amino acid and the peptide bonds it forms with other residues
An amino acid residue side chain is deprontonated at pH9.5. What is the pKa of this residue if it is fully deprotonated at this pH?
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His-Tyr
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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- 22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forward22-61 Polyglutamic acid (a polypeptide chain made only of glutamic acid residues) has an a-helix conformation below pH 6.0 and a random-coil conformation above pH 6.0. What is the reason for this conformational change?arrow_forwardA peptide has the sequence Glu–His–Trp–Ser–Gly–Leu–Arg–Pro–Gly The p?a values for the peptide’s side chains, terminal amino groups, and carboxyl groups are provided in the table. Amino acid Amino pKa Carboxyl pKa Side‑chain pKa glutamate 9.609.60 2.342.34 4.254.25 histidine 9.179.17 1.821.82 6.006.00 tryptophan 9.399.39 2.382.38 serine 9.159.15 2.212.21 glycine 9.609.60 2.342.34 leucine 9.609.60 2.362.36 arginine 9.049.04 2.172.17 12.4812.48 proline 10.9610.96 1.991.99 Calculate the net charge of the molecule at pH 11 and estimate the isoelectric point (pI)(pI) for this peptide.arrow_forward
- Write the structural formula (flat projection) of the dipeptide glycyl-phenylalanine (Glycine is the N-terminal residue). What electrical charge will this dipeptide have at pH 7.0?arrow_forwardHis-Met-Asp-Tyr-Phe-Ser within this peptide, which amino acid residue is the most hydrophobic and why?arrow_forwardThe initial pH of a 2M arginine solution is 14. What is the predominant structure of arginine in solution at this pH?arrow_forward
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