Package: Organic Chemistry with Connect 2-year Access Card
5th Edition
ISBN: 9781259729959
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 29, Problem 29.34P
Tryptophan is not classified as a basic amino acid even though it has a heterocycle containing a nitrogen atom. Why is the
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Histidine is classified as a basic amino acid because one of the N atoms in its five-membered ring is readily protonated by acid. Which N atom in histidine is protonated and why?
Histidine is classied as a basic amino acid because one of the N atoms in its fivemembered ring is readily protonated by acid. Which N atom in histidine is protonated and why?
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.
Chapter 29 Solutions
Package: Organic Chemistry with Connect 2-year Access Card
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 - Prob. 29.4PCh. 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 - Problem 29.9
Draw the products of each...Ch. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Problem 29.15
Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 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. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 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. 29.32PCh. 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 - 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 - 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. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 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. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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- Answer the following questions about the amino acid whose Fischer projection formula is a. Is it a D-amino acid or an L-amino acid? b. Is it a nonpolar or polar amino acid? c. Is it an essential or nonessential amino acid? d. Is it a standard or nonstandard amino acid?arrow_forwardWhat percentage of the a-amino group of lysine will be protonated at its pI? < 25% 50% > 75% a. Answer the same question for the e-amino group of lysine.arrow_forwardDraw the structure of alanine in a solution at pH = 0arrow_forward
- What percentage of the e-amino group of lysine will be protonated at its pI?< 25% 50% >75%arrow_forwardWhen an unprotected -amino acid is treated with dicyclohexylcarbodiimide (DCC), a 2,5-diketopiperazine results. Explainarrow_forwardDraw the structure of the amino acid L-leucine at each pH: (a) 6; (b) 10; (c) 2. Which form predominates at L-leucine's isoelectric point?arrow_forward
- Draw the structure of the following moleculeThe amino acid lysine at pH 12arrow_forwardLysine and tryptophan are two amino acids that contain an additional N atom in the R group bonded to the α carbon. While lysine is classied as a basic amino acid because it contains an additional basic N atom, tryptophan is classied as a neutral amino acid. Explain why this difference in classication occurs.arrow_forwardExplain why the ability of PLP to catalyze an amino acid transformation is greatly reduced if a PLP-requiring enzymatic reaction is carried out at a pH at which the pyridine nitrogen is not protonated.arrow_forward
- With 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_forwardLeuprolide is a synthetic nonapeptide used to treat both endometriosis in women and prostate cancer in men. (a) Both C-terminal and N-terminal amino acids in leuprolide have been structurally modified. Identify the modifications. (b) One of the nine amino acids in leuprolide has d stereochemistry rather than the usual L. Which one? (c) Write the structure of leuprolide using both one- and three-letter abbreviations. (d) What charge would you expect leuprolide to have at neutral pH?arrow_forward
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