EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 15, Problem 91P
Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of the antibody is carried out in the presence of a transition state analog—a stable molecule that structurally resembles the transition state. This causes an antibody to be generated that recognizes and binds to the transition state, thereby stabilizing it. For example, the following transition state analog has been used to generate a catalytic antibody that catalyzes the hydrolysis of the structurally similar ester:
a. Draw a possible transition state for the hydrolysis reaction.
b. The following transition state analog is used to generate a catalytic antibody for the catalysis of ester hydrolysis. Draw the structure of an ester whose rate of hydrolysis would he increased by this catalytic antibody.
c. Design a transition state analog that catalyzes amide hydrolysis at the amide group indicated.
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Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of the antibody is carried out in the presence of a transition state analog—a stable molecule that structurally resembles the transition state. This causes an antibody to be generated that recognizes and binds to the transition state, thereby stabilizing it. For example, the following transition state analog has been used to generate a catalytic antibody that catalyzes the hydrolysis of the structurally similar ester:
a. Draw a possible transition state for the hydrolysis reaction. b. The following transition state analog is used to generate a catalytic antibody for the catalysis of ester hydrolysis. Draw the structure of an ester whose rate of hydrolysis would be increased by this catalytic antibody.
Select below all the catalytic mechanisms used by
chymotrypsin to convert substrate into product.
metal ion catalysis
covalent catalysis
acid-base catalysis
Based on the experiment described below determine the Michaelis constant of the enzyme involved to two decimal places. Include any appropriate units. In your working out do not round intermediate results and only round the final value as required.
A student in studied the kinetics of acid phosphatase. Acid phosphatase hydrolyses p-nitrophenyl phosphate into phosphate and p-nitrophenol.
Reactions contains 250 microlitres p-nitrophenyl phosphate, 50 microlitres 0.1mg.ml/-1 acid phosphatase and 200 microlitres 100mM citrate buffer pH 4.8
They measured the initial rate of enzyme activity (nmol p-nitrophenol produced/min) for different concentrations of p-nitrophenyl phosphate (mmol/L) included in the reaction. The collected data was transformer, a Lineweaver Burk plot, similar to the general one depicted below, was created and the straight-line equation generated from the fitted data.
Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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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
- List two ways that enzyme catalysis of a reaction is superior to normal conditions.arrow_forwardAmylase’ is an enzyme in our saliva that digests the ‘amylose’ protein in mouth. How could you justify the mechanism of enzymatic action using enzyme-catalyzed reaction models?arrow_forwardDraw a reaction coordinate diagram in which the structure of the transition site is more similar to the product of the reaction than to the reactant.arrow_forward
- The Michaelis-Menten equation is an expression of the relationship between the initial velocity Vo of an enzymatic reaction and substrate concentration [S]. There are three conditions that are useful for simplifying the Michaelis-Menten equation to an expression from which the effect of [S] on the rate can be more readily determined. Match the condition (e.g., [S] = Km) with the statement or statements that describe it. Doubling [S] will almost double the rate. Half of the active sites are occupied by substrate. About 90% of the active sites are occupied by substrate. Doubling [S] will have little effect on the rate. Less than 10% of the active sites are occupied by substrate. This condition will result in the highest rate. Answer Bank [S] = 0.1 Km [S] = Km [S] = 10 Kmarrow_forwardPlease don't provide handwritten solution ....arrow_forwardDraw the complete electron pushing mechanism that is enzyme catalyzed.arrow_forward
- If a fast step precedes a slow step in a two-step mecha-nism, how is the fast step affected? How is this effect used to determine the validity of the mechanism?arrow_forwardLet's try similar things with another enzyme! Here's one with a cool mechanism that makes an interesting product. Cys157 Cys157 Cys157 His296 His296 His296 OH HNN: HN, HN -CO2 CH2 Asn329 Asn329 Asn329- Cys157 His296 OH OH HNNH HC. Asn329 N Note that this figure is typical of those found in the biochemical literature in that it provides a somewhat abbreviated view of what is happening. For example, the arrows I have circled in red above for the fırst step need some sorting out. What mechanism is represented by these arrows? O a two step, addition/elimination reaction O an SN2 reaction O an SN1 reaction O nucleophilic aromatic substitution O electrophilic aromatic substitutionarrow_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
- Chemistry Use the References to access important values if needed for this question. Suppose a sequence of enzymatically catalyzed reactions converts substrate A to final product D through a sequem reactions involving the production of intermediate products B and C as shown. Product D inhibits enzyme E₁. If the enzymes E₁-E3 are all present in a test tube and substrate A is added to the reaction mixture, how will the concentration of product D change? E₁ E₂ E3 A B C D increase to a fixed value first increase, then decrease remain at zero oscillate between zero and the concentration of A added increase to the concentration of A added Submit Answer Try Another Version 1 item attempt remainingarrow_forwardUnder acidic conditions (such as in your stomach) benzyl penicillin (BP) breaks down to three products which we will call A, B, and C in a parallel reaction with the following A BP B. values for the rate constants: ka = 7.0 × 10-4 sec-1; ks = 4.1 x 10-3 sec-1; and ke 5.7 x 10-3 sec-1. What is the yield of product A? In other words, after the reaction has reached completion what fraction of the product is present as compound-A?arrow_forwardReview the structure of the standard amino acids and listthose that are capable of acting as acids or bases in enzymecatalysis. Are there any that can function as either acids orbases?arrow_forward
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