Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 29, Problem 29.17P
Glutathione, a powerful antioxidant that destroy s harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:
glutathione
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?
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Students have asked these similar questions
Which amino acids on proteins can form glycosidic linkages?
Select one:
a. Cysteine and methionine
b. Tryptophan and phenylalanine
c. Glycine and proline
d. Serine and asparagine
e. Alanine and leucine
9. A trisaccharide obtained from the partial hydrolysis of amylopectin showed two glycosidic
linkages.
A. Draw the structure of the trisaccharide
B. If the trisaccharide is to be exhaustively methylated and subsequently hydrolyzed with
an acid, how many different methylated products will be obtained? Draw their
structures.
C. Can an aqueous solution of the trisaccharide precipitate Cu as Cu₂O? If it can, encircle
the potential carbonyl carbon(s) in the trisaccharide.
D. Can the trisaccharide exist in different anomeric forms? If yes, draw their structures.
B. Draw the structure of the following dipeptide. Use the formation of polymers
to draw.
1. Ser - Ala
Chapter 29 Solutions
Organic Chemistry
Ch. 29 - Prob. 29.1PCh. 29 - Problem 29.2
What form exists at the isoelectric...Ch. 29 - Problem 29.3
Explain why the of the group of an...Ch. 29 - Problem 29.5
What -halo carbonyl compound is...Ch. 29 - Problem 29.6
The enolate derived from diethyl...Ch. 29 - Problem 29.7
What amino acid is formed when is...Ch. 29 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 29 - Prob. 29.8PCh. 29 - Prob. 29.9PCh. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Name each peptide using both the one-letter and...Ch. 29 - Prob. 29.15PCh. 29 - Prob. 29.16PCh. 29 - Problem 29.18
Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19
Draw the structure of the...Ch. 29 - Problem 29.20
Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.21PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.24PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.27PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.31PCh. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - To calculate the isoelectric point of amino acids...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - Draw the organic product formed when the amino...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - Prob. 29.48PCh. 29 - Prob. 29.49PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.51PCh. 29 - Prob. 29.52PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 29 - Prob. 29.55PCh. 29 - Explain why a peptide CN bond is stronger than an...Ch. 29 - Prob. 29.57PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.59PCh. 29 - Prob. 29.60PCh. 29 - Prob. 29.61PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - Prob. 29.63PCh. 29 - Prob. 29.64PCh. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - Which of the following amino acids are typically...Ch. 29 - After the peptide chain of collagen has been...Ch. 29 - Prob. 29.72PCh. 29 - Prob. 29.73PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.75P
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- 9. Which of the following amino acids has more than one chiral center a. b. C. d. е. ETFarrow_forwardA trisaccharide obtained from the partial hydrolysis of amylopectin showed two glycosidic linkages. A. Draw the structure of the trisaccharide B. If the trisaccharide is to be exhaustively methylated and subsequently hydrolyzed with an acid, how many different methylated products will be obtained? Draw their structures. C. Can an aqueous solution of the trisaccharide precipitate Cu as Cu2O? If it can, encircle the potential carbonyl carbon(s) in the trisaccharide. D. Can the trisaccharide exist in different anomeric forms? If yes, draw their structures.arrow_forwardCeramide can then be used to synthesize sphingomyelin, another important molecule that is prevalent in cell membranes. 1.How does the structure of sphingomyelin differ from that of ceramide? 2.Sphingomyelin is also found in the cell membrane. Explain how you would expect to find the orientation of this molecule in the cell membrane. 3.Which amino alcohol is used in the synthesis of sphingomyelin? 4.What is particular about the amino alcohol used in in the synthesis of sphingomyelin? 5.How does your answer to #16 affect the physical properties of properties of sphingomyelin?arrow_forward
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