Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 29, Problem 29.22P
Devise a synthesis of each peptide from amino acid starting materials: (a) Leu–Val; (b) Ala–Ile–Gly.
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Devise a synthesis of each peptide from amino acid starting materials: (a) Leu–Val; (b) Ala–Ile–Gly; (c) Ala–Gly–Ala–Gly.
Draw the structure for each peptide: (a) Phe–Ala; (b) Gly–Gln; (c) Lys–Gly; (d) R - H.
Draw both enantiomers of each amino acid and label them as R or S: (a) phenylalanine; (b) methionine.
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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- Name each peptide using both the three-letter and one-letterabbreviations of the component amino acids.arrow_forwardWith reference to the following peptide: (a) Identify the N-terminal and Cterminal amino acids. (b) Name the peptide using one-letter abbreviations. (c) Label all the amide bonds in the peptide backbone.arrow_forwardDraw the amino acids and peptide fragments formed when the decapeptide A–P–F–L–K–W–S–G–R–G is treated with each reagent or enzyme: (a) chymotrypsin; 8 pt helvetica roman (b) trypsin; (c) carboxypeptidase; (d) C6H5N = C = S.arrow_forward
- (a) Draw the structure of the two possible dipeptides that can be formed by combining valine and phenylalanine. (b) In each dipeptide, label the N- and C-terminal amino acids. (c) Name each peptide using three-letter symbols.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_forwardDraw both enantiomers of each amino acid and label them as D or L: (a) methionine; (b) asparaginearrow_forward
- Propose a synthesis for the peptide leu-lys-cysarrow_forwardPlease give a clear explanation handwritten answer..arrow_forwardFor the tripeptide SerValMet 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
- The following compound is an intermediate in the biosynthesis of one of the 20 common -amino acids. Which one is it likely to be, and what kind of chemical change must take place to complete the biosynthesis?arrow_forward22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forwardWhich amino acids could be referred to as derivatives of butanoic acid?arrow_forward
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