Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 15, Problem 30P
A number of drugs are prepared by reactions in which carbon–carbon bond formation is the last step. Indicate what you believe would be a reasonable last step in the synthesis of each
of the following:
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Prostaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in
prostaglandin synthesis involves the conversion of the 20-carbon fatty acid arachidonic acid to PGG2 by the enzyme prostaglandin endoperoxide synthase, or cyclooxy:
Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically.
Arachidonic acid
20₂
0.5
1.0
1.5
2.5
3.5
cyclooxrygenase
PGG₂
JOH
محمد
The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48
[arachidonic acid] (uM)
(1) v(uM/min) (2) v(uM/min)
23.5
32.2
36.9
41.8
44.0
16.67
25.25
30.49
37.04
38.91
Ibuprofen
A. Plot the data in standard Michaelis-Menten form as well as in double-reciprocal form.
B. Determine Vmax and Km for the enzyme.
C. Based on this limited data set, what type of inhibition does ibuprofen likely exhibit?…
Prostaglandins are a class of cicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues.
They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20-
carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a
cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins.
Rate of formation of PGG2 with 10 mg/ml
ibuprofen (mM/min)
Arachidonic
acid (mM)
Rate of formation
of PGG2 (mM/min)
0.190
12.3
0.228
13.9
0.342
17.5
0.570
1.33
22.2
28.8
7.71
8.88
11.9
16.3
24.0
The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing
here on the first two columns, determine the Vmax and Km of the enzyme.
Vmax =
Km
mM/min
mM
Exercice 5 Complete the following reactions, giving details of the reaction mechanisms Exercice 6 Give
the compound A formed in the following reaction → NaOH
Chapter 15 Solutions
Organic Chemistry - Standalone book
Ch. 15.1 - Each of the following organometallic reagents will...Ch. 15.3 - Write equations showing how you could prepare...Ch. 15.4 - Lithium diisopropylamide is often used as a strong...Ch. 15.5 - Write the structure of the organic product of each...Ch. 15.7 - Prob. 5PCh. 15.8 - Prob. 6PCh. 15.9 - Prob. 7PCh. 15.9 - Like nickel, iron reacts with carbon monoxide to...Ch. 15.9 - Prob. 9PCh. 15.9 - What is the oxidation state of manganese in the...
Ch. 15.9 - Prob. 11PCh. 15.10 - Prob. 12PCh. 15.10 - Prob. 13PCh. 15.11 - Give the structure including stereochemistry of...Ch. 15.11 - Prob. 15PCh. 15.12 - Homogeneous catalytic hydrogenation of the...Ch. 15.12 - Prob. 17PCh. 15.13 - What alkenes are formed from 2-pentene by olefin...Ch. 15.13 - The product of the following reaction was isolated...Ch. 15 - Suggest appropriate methods for preparing each of...Ch. 15 - Prob. 21PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 23PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 25PCh. 15 - A different stereoisomer of...Ch. 15 - Prob. 27PCh. 15 - Using phenyllithium and any necessary organic or...Ch. 15 - Prob. 29PCh. 15 - A number of drugs are prepared by reactions in...Ch. 15 - The following conversion was carried out in two...Ch. 15 - Outline syntheses of (a)...Ch. 15 - (S)-(+)-Ibuprofen can be prepared by...Ch. 15 - Like other hydroborations, the reaction of alkynes...Ch. 15 - The sex attractant of the female silkworm has been...Ch. 15 - Prob. 36PCh. 15 - (a) Exaltolide, a musk substance, has been...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and (Cyclobutadiene)tricarbonyliron...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...
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