ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 27, Problem 70P
The anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without
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Esterase is an enzyme that catalyzes the hydrolysis of esters. It hydrolyzes esters of L-amino acids more rapidly than esters of d-amino acids. How can this enzyme be used to separate a racemic mixture of amino acids?
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
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(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
enzyme.
(C) Urea causes the enzyme to denature and lose its
specific three-dimensional shape.
(D) Urea reacts with disulfide bonds in the enzyme.
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.
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The first step in the catabolism of most amino acids is the removal of the nitrogen atom by transfer to an a-keto acid, a reaction catalyzed by an enzyme called a transaminase. The a-keto acid acceptor is often a-ketoglutarate. Modify the structures in the product to show the products of the transamination of cysteine. Be sure to show functional groups with the charge and number of attached hydrogen atoms appropriate for pH 7.4. transaminase + O=C H₂N-CH + CH₂ CH₂ CH₂ SH Incorrect H₂N || CH | CH₂ | CH₂ I || O || n | CH₂ T SHarrow_forwardProteins are thermodynamically unstable molecules since the Delta G of hydrolysis is quite negative. However, most proteins are not degraded unless they come into contact with proteases in cells. What is the reasoning for this paradox? The reaction is endergonic and will not proceed without energy. There is very little water inside cells to react with protein molecules. The free energy change doesn't reveal anything about the rate of the reaction. The concentration of proteins are low which allows them to be more stable.arrow_forward1. What reaction is catalyzed by the enzyme carbonic anhydrase? Which metal ion serves as a cofactor for carbonic anhydrase? Explain how this metal ion is able to assist in catalyzing the reaction. 2. In relation to enzymes, what is the difference between a cosubstrate and a prosthetic group? Give one example of each.arrow_forward
- It is known that the amino acid at position 523 of the cyclooxygenase enzyme is part of the active site. In the isoenzyme COX-1, this amino acid is isoleucine, whereas in COX-2, it is valine. Suggest how such information could be used in the design of drugs that selectively inhibit COX-2.arrow_forwardTriosephosphate isomerase (TIM) catalyzes the conversion of dihydroxyacetone phosphate to glyceraldehyde-3-phosphate. The enzyme’s catalytic groups are Glu 165 and His 95. In the first step of the reaction, these catalytic groups function as a general-base and a general-acid catalyst, respectively. Propose a mechanism for the reaction.arrow_forwardChorismate mutase is an enzyme that promotes a pericyclic reaction by forcing the substrate to assume the conformation needed for the reaction. The product of the pericyclic reaction is prephenate that is subsequently converted into the amino acids phenylalanine and tyrosine. What kind of a pericyclic reaction does chorismate mutase catalyze?arrow_forward
- As you increase the temperature of an enzyme-catalyzedreaction, the rate of the reaction initially increases. It thenreaches a maximum rate and finally dramatically declines.Keeping in mind that enzymes are proteins, how do youexplain these changes in reaction rate?arrow_forwardWhat is the transition state in an enzyme- catalyzed reaction.arrow_forwardActivation of a zymogen is by covalent modification. How might phosphorylation or dephosphorylation (also covalent modification) modify an enzyme to make it more active (or more inactive)?arrow_forward
- If an enzyme-catalyzed reaction has a high rate at low pH and low rate at higher pH, this implies that a group on either the enzyme or the substrate must be for an efficient reaction. leaving group oxidoreductase coenzymes O protonated deprotonated The compound that consists of deoxyribose linked by an N-glycosidic bond to N-9 of guanine is: adenylate deoxyguanosine guanosine nucleotide guanylatearrow_forwardAcetylcholine esterase is an important enzyme in neural synaptic signal transmission. It breaks down the neurotransmitter acetylcholine after it binds the acetylcholine receptor. Its active site has the same features used by serine proteases. Here is the reaction catalyzed by Acetylcholine esterase: Acetylcholine Choline OH Acetate + H Acetylcholine is an ester, while peptide bonds cleaved by proteases are amides. How should acetylcholine estease's mechanism accommodate this? This cannot be determined from the information presented in class and in this question. For amides, the amide nitrogen is deprotonate to make it more like an ester. The same mechanism cleaves deprotonated amides and esters. No changes are needed. The mechanism same works for esters and amides. Prior to cleavage, a transamination converts the ester to an amide. The esterase will make a covalent intermediate to an amine to create the amide to be cleaved.arrow_forwardChorismate mutase is an enzyme that promotes a pericyclic reaction by forcing the substrate to assume the conformation needed for the reaction. The product of the pericyclic reaction is prephenate that is subsequently converted into the amino acids phenylalanine and tyrosine. What kind of a pericyclic reaction does chorismate mutase catalyze?arrow_forward
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