Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 27, Problem 65P
Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:
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Neostigmine is an inhibitor of acetylcholinesterase. The enzyme attempts to catalyse the same reaction on neostigmine as it does with acetylcholine. However, a stable intermediate is formed which prevents completion of the process and which results in a molecule being covalently linked to the active site. Identify (draw) the stable intermediate and explain why it is stable.
Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under these conditions:
An enzyme catalyzes the hydrolysis of an ester with a
certain activity, but this activity is lost in a 3 M urea
solution. What is the most likely explanation for the loss
of activity?
(A) Urea binds to the active site of the enzyme
competitively with the substrate.
(B) Urea causes the cleavage of the peptide bonds in the
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(C) Urea causes the enzyme to denature and lose its
specific three-dimensional shape.
(D) Urea reacts with disulfide bonds in the enzyme.
Chapter 27 Solutions
Organic Chemistry (6th Edition)
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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- Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:arrow_forwardlodoacetamide acts as an irreversible inhibitor for a few enzymes by reacting with the amino acid at the active site having the function group -NH_2 -COOH -SH -OHarrow_forwardProteins that helps in increasing the rate of chemical reaction in the body * O(a) Enzymes O (b) Antibody O (c) Structural proteins O (d) Transport proteinsarrow_forward
- What is the mechanism of action of the antibiotic drug Sulfanilamide in terms of enzyme inhibition?arrow_forwardThe conversion of L-proline to D-proline is shown. The reaction below shows an enzyme-catalyzed reaction that converts from an L amino acid to D amino acid. What type of enzyme catalyzes this reaction? H H+ COOH L-Proline Isomerase Hydrolase Ligase Transferase COOH Transition state H Xco N COOH H D-Prolinearrow_forwardPredict the product(s) obtained when each of the following compounds is treated with a mixture of nitric acid and sulfuric acid. Select all that apply. 18.41d * Your answer is incorrect.arrow_forward
- Sulfanilamide, a sulfur drug, acts as an antibiotic. Explain its mechanism of action in the context of enzyme inhibition. Methotrexate is used in cancer chemotherapy. Explain how this compound works by elaborating on the type of enzyme inhibition involved for its action.arrow_forwardHow prepare g-C3N4 from urea in laboratory?arrow_forwardGive the name of the enzyme that will most likely catalyze each of the following reactions: O CH3 - CH2 - OH + NAD+ → CH3 – C – H + NADH + H+ Ans. ___________________________________________ CH3 – C – COOH + R – CH – COOH → CH3 – CH – COOH + R – C – COOH O NH2 NH2 O HO – C – CH – CH2 – C – OH → HO – C – CH = CH – C – OH + H2O O OH O O O CO2 + CH3 – C – C – OH + ATP → HO – C – CH2 – C – C – OH + ADP + Pi O O O O…arrow_forward
- 3. What is the product if the following peptide is hydrolyzed? H₂N O OHarrow_forwardBelow is given the active site of a protease including its substrate. SUBSTRATE R1-NH NH Ph NH OH N ENZYME (i) Which type of protease is this? (ii) Draw the same part of the enzyme at the intermediate stage of the enzyme catalyzed reaction when part of the substrate is covalently linked to the enzyme.arrow_forwardSome nonessential amino acids are synthesized in the body by a simple transamination. The transamination between oxaloacetate, an a-keto acid, and glutamate, an amino acid with the side chain -CH2CH2COO¯, proceeds according to the following reaction: || → -00C-CH2 CH2 C-CO0 + amino acid 2 0OC-CH2 CCOO +0OC-CH2 CH2 CH-COO → NH3+ Predict the structure of the amino acid product, indicated by amino acid 2, for the reaction. Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. Include all hydrogen atoms and formal charges. Viouarrow_forward
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