ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 27.2, Problem 8P
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Draw both enantiomers of each amino acid and label them as R or S: (a) phenylalanine; (b) methionine.
Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.
a. Val–Glu
b. Gly–His–Leu
c. M–A–T–T
A tripeptide undergoes complete hydrolysis and the resulting mixture contains only phenylalanine and glycine. Draw all possible sequences for the original tripeptide.
Chapter 27 Solutions
ORGANIC CHEMISTRY
Ch. 27.1 - Prob. 1PCh. 27.1 - Problem 29.2
What form exists at the isoelectric...Ch. 27.1 - Problem 29.3
Explain why the of the group of an...Ch. 27.1 - Prob. 4PCh. 27.2 - Problem 29.5
What -halo carbonyl compound is...Ch. 27.2 - Problem 29.6
The enolate derived from diethyl...Ch. 27.2 - Problem 29.7
What amino acid is formed when is...Ch. 27.2 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 27.2 - Problem 29.9
Draw the products of each...Ch. 27.3 - Prob. 10P
Ch. 27.3 - Prob. 11PCh. 27.3 - Prob. 12PCh. 27.4 - Problem 29.13
What alkene is needed to synthesize...Ch. 27.5 - Problem 29.14
Draw the structure of each peptide....Ch. 27.5 - Problem 29.15
Name each peptide using both the...Ch. 27 - Draw the product formed when the following amino...Ch. 27 - With reference to the following peptide: a...Ch. 27 - Prob. 31PCh. 27 - Histidine is classified as a basic amino acid...Ch. 27 - Tryptophan is not classified as a basic amino acid...Ch. 27 - What is the structure of each amino acid at its...Ch. 27 - What is the predominant form of each of the...Ch. 27 - 29.37 What is the predominant form of each of the...Ch. 27 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 27 - 29.39 Draw the organic products formed in each...Ch. 27 - 29.40 What alkyl halide is needed to synthesize...Ch. 27 - Prob. 50PCh. 27 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 27 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 27 - Prob. 53PCh. 27 - Prob. 54PCh. 27 - 29.55 Draw the amino acids and peptide fragments...Ch. 27 - Prob. 56PCh. 27 - Prob. 57PCh. 27 - Prob. 58PCh. 27 - 29.59 An octapeptide contains the following amino...Ch. 27 - 29.60 Draw the organic products formed in each...Ch. 27 - 29.65 Draw the mechanism for the reaction that...Ch. 27 - 29.66 Which of the following amino acids are...Ch. 27 - 29.67 After the peptide chain of collagen has been...Ch. 27 - Prob. 68PCh. 27 - Prob. 69PCh. 27 - 29.70 The anti-obesity drug orlistat works by...Ch. 27 - Prob. 71P
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- What special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?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_forwardFor the tripeptide GlyAlaCys a. What amino acid is located at the peptides N-terminal end? b. What amino acid is located at the peptides C-terminal end? c. How many peptide bonds are present? d. How many amide linkages are present?arrow_forward
- General reactions for drugs belonging to the group of aliphatic amino acids: A) with iodine solution B) With ninhydrin C) With copper sulfate in an alkaline environment D) With resorcinolarrow_forwardDraw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin, appeared in Section 22.6B.)arrow_forwardTreating chitin with H2O, -OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, bers for sutures, and wound dressings.arrow_forward
- Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.arrow_forward1.Draw the structures of ornithine and lysine. Explain how they are different . (B) Draw the structure of the compound formed when ornithine reacts with carbamoyl phosphate. (C) Write the transamination reaction of alanine with alpha - ketoglutarate. Name the products that are formed .arrow_forwardDraw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu.arrow_forward
- 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.arrow_forward1. In the synthesis of p-amino benzene sulfonamide, a bubble formation is duw to the formation of _? 2. Draw the sulfonic acid and its derivatives.arrow_forward3. What is the product if the following peptide is hydrolyzed? H₂N O OHarrow_forward
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