Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24.4, Problem 24.6P
Although tryptophan contains a heterocyclic
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Although tryptophan contains a heterocyclic amine, it is considered a neutral aminoacid. Explain why the indole nitrogen of tryptophan is more weakly basic than one ofthe imidazole nitrogens of histidine.
Lanthionine is a nonstandard amino acid consisting of two alanine residues linked via their β carbon atoms by a thioether (—S—) linkage. Draw the structure of lanthionine.
Lysine and tryptophan are two amino acids that contain an additional N atom in the R group bonded to the a carbon. While lysine is classified as a basic amino acid because it contains an additional basic N atom, tryptophan is classified as a neutral amino acid. Explain why this difference in classification occurs.
Chapter 24 Solutions
Organic Chemistry (9th Edition)
Ch. 24.2A - Draw three-dimensional representations of the...Ch. 24.2A - Prob. 24.2PCh. 24.2B - The herbicide glyphosate (Roundup) kills plants by...Ch. 24.4 - Draw the structure of the predominant form of a....Ch. 24.4 - Draw the resonance forms of a protonated guanidino...Ch. 24.4 - Although tryptophan contains a heterocyclic amine,...Ch. 24.4 - Prob. 24.7PCh. 24.4 - Prob. 24.8PCh. 24.5A - Show how the following amino acids might be formed...Ch. 24.5B - Prob. 24.10P
Ch. 24.5C - Prob. 24.11PCh. 24.5C - Show how you would use a Strecker synthesis to...Ch. 24.6 - Suggest how you would separate the free i-ammo...Ch. 24.7A - Propose a mechanism for the acid-catalyzed...Ch. 24.7A - Give equations for the formation and...Ch. 24.7B - Prob. 24.16PCh. 24.7C - Prob. 24.17PCh. 24.8B - Draw the complete structures of the following...Ch. 24.9C - Prob. 24.19PCh. 24.9C - Prob. 24.20PCh. 24.9C - Prob. 24.21PCh. 24.9E - Prob. 24.22PCh. 24.9E - Prob. 24.23PCh. 24.10A - Propose a mechanism for the coupling of acetic...Ch. 24.10B - Show how you would synthesize Leu-Gly-Ala-Val-Phe...Ch. 24.10B - Show how solid-phase peptide synthesis would be...Ch. 24 - a. The isoelectric point (pl) of phenylalanine is...Ch. 24 - Prob. 24.28SPCh. 24 - Prob. 24.29SPCh. 24 - Prob. 24.30SPCh. 24 - Prob. 24.31SPCh. 24 - Suggest a method for the synthesis of the...Ch. 24 - Prob. 24.33SPCh. 24 - Write the complete structures for the following...Ch. 24 - The following structure is drawn in an...Ch. 24 - Prob. 24.36SPCh. 24 - Prob. 24.37SPCh. 24 - Show the steps and intermediates in the synthesis...Ch. 24 - Prob. 24.39SPCh. 24 - Lipoic acid is often found near the active sites...Ch. 24 - Prob. 24.41SPCh. 24 - Prob. 24.42SPCh. 24 - Prob. 24.43SPCh. 24 - Complete hydrolysis of an unknown basic...Ch. 24 - Prob. 24.45SPCh. 24 - Prob. 24.46SPCh. 24 - Prob. 24.47SP
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- What special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forwardA chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forward22-91 Which amino acid does not rotate the plane of polarized light?arrow_forward
- Draw a structural formula for the product formed when alanine is treated with the following reagents. (a) Product from (c), L-Alanine ethyl ester, DCC (b) Product from (d), L-Alanine ethyl ester, DCCarrow_forward22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forwardOn complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one phenylalanine, and one valine residue. Partial hydrolysis gives the following fragments: Ala-Phe, Leu-Met, Val-Ala, Phe-Leu. It is known that the first amino acid in the sequence is valine and the last one is methionine. What is the complete sequence of amino acids?arrow_forward
- 22-21 Explain why an amino acid cannot exist in an un-ionized form at any pH.arrow_forwardConsider the tripeptide leucylvalyltryptophan. a. Specify its structure using three-letter symbols for the amino acids. b. How many peptide bonds are present within the peptide? c. Which of the amino acid residues has the largest R group? d. Which of the amino acid residues, if any, has a basic side chain?arrow_forward22-48 How many amino acid residues in the A chain of insulin are the same in insulin from humans, cattle (bovine), hogs, and sheep?arrow_forward
- 22-17 What are the similarities and differences in the structures of alanine and phenylalanine?arrow_forward22-44 How can a protein act as a buffer?arrow_forwardAnother method to form a peptide bond involves a two-step process Reaction of the p-nitrophenyl ester with an amino acid ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forward
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